- IDENTIFICATION OF NAA-L-ASPARTATE AMIDE AS THE MAJOR METABOLITE SYNTHESIZED BY TOBACCO MESOPHYLL PROTOPLASTS INCUBATED IN THE PRESENCE OF THE AUXIN ANALOGUE NAA
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A major metabolite of naphthalene 1-acetic acid (NAA) is rapidly accumulated by tobacco mesophyll protoplasts induced to divide by this growth regulator.A comparison of the natural product with various chemically synthesized NAA-amino acid conjugates was performed.Themetabolite was identified as NAA-aspartate amide by negative CIMS.The biological activity of NAA-aspartate on protoplasts was further studied.The significance of the accumulation of this metabolite in dividing protoplasts is descussed.Key words: Nicotiana tabacum; Solanaceae; protoplast; NAA; auxin-amino acid; conjugates; isolation; identification.
- Aranda, Gerard,Tabet, Jean-Claude,Leguay, Jean-Jacques,Caboche, Michel
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- Peri-Dimethylamino substituent effects on proton transfer at carbon in α-naphthylacetate esters: A model for mandelate racemase
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The rate constants for exchange of hydrogen for deuterium at the α-CH2 positions of 8-(N,N-dimethylaminonaphthalen-1-yl)acetic acid tert-butyl ester 1 and naphthalen-1-ylacetic acid tert-butyl ester 2 have been determined in potassium deuteroxide solutions in 1:1 D2O:CD 3CN, in order to quantify the effect of the neighbouring peri-dimethylamino substituent on α-deprotonation. Intramolecular general base catalysis by the (weakly basic) neighbouring group was not detected. Second-order rate constants, kDO, for the deuterium exchange reactions of esters 1 and 2 have been determined as 1.35 × 10-4 M-1 s-1 and 3.95 × 10-3 M-1 s-1, respectively. The unexpected 29-fold decrease in the k DO value upon the introduction of a peri-dimethylamino group is attributed to an unfavourable steric and/or electronic substituent effect on intermolecular deprotonation by deuteroxide ion. From the experimental k DO values, carbon acid pKa values of 26.8 and 23.1 have been calculated for esters 1 and 2.
- Delley, Richard J.,Bandyopadhyay, Subhajit,Fox, Mark A.,Schliehe, Constanze,Hodgson, David R. W.,Hollfelder, Florian,Kirby, Anthony J.,O'Donoghue, Annmarie C.
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- L-Amino acid derived pyridinium-based chiral compounds and their efficacy in chiral recognition of lactate
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A series of pyridinium-based chiral compounds 1-6 have been designed and synthesized. l-Amino acids have been used as the chiral source in the molecules. Among the chiral compounds, an l-valine derived compound 1 was found to exhibit enantioselective recognition of d-lactate in fluorescence. Structural tuning of this derivative, either by replacing l-valine with l-alanine or l-phenylglycine or by reducing the number of chiral centres around the binding site, does not result in any significant change in enantioselectivity in the recognition process. Change of the urea site to amide introduces compound 6 that displays good enantiodiscrimination for lactate (enantiomeric fluorescence difference ratio ef = 28.33 for d-lactate), even better than that of the l-valine derived compound 1 and of other reported structures in the literature.
- Ghosh, Kumaresh,Majumdar, Anupam
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- A ratiometric luminescent sensing of Ag+ ion via in situ formation of coordination polymers
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A ratiometric luminescent sensing of Ag+ ion is developed via the Ag(i)-NCys coordination polymeric luminophore in situ formed in aqueous solution upon mixing Ag+ ion with the designed fluorescent thiol ligand NCys.
- Li, Dong-Hua,Shen, Jiang-Shan,Chen, Na,Ruan, Yi-Bin,Jiang, Yun-Bao
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- Synthesis, characterization and slow release properties of O-naphthylacetyl chitosan
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O-naphthylacetyl chitosan (NA-chitosan) was first prepared via protecting the amino groups with phthalic anhydride, followed by reaction with 1-naphthylacetyl chloride. The intermediates were hydrolyzed with anhydrous hydrazine to obtain final product. The derivatives of each step were characterized with Fourier transform infrared spectroscopy (FT-IR) and 13C solid state nuclear magnetic resonance (NMR). Results showed NA-chitosan had both naphthylacetyl and amino groups in the main chain of the polysaccharide. Elemental analysis showed that the substitution degree of hydroxyl was 0.4. Thermogravimetric analysis (TGA, DTG) of NA-chitosan was observed with much lower decomposition peak at 283°C than that of chitosan at 300°C. The release of 1-naphthylacetic acid was dependent on both pH values and the medium temperature, and at pH 12.0, 60°C the release period could last for 55 days.
- Tao, Shuming,Pang, Ran,Chen, Chao,Ren, Xueqin,Hu, Shuwen
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- Pyridinum-based flexible tripodal cleft:A case of fluorescence sensing of ATP and dihydrogenphosphate under different conditions and cell imaging
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Pyridinium-based chemosensor 1 built on tris(aminomethyl)amine (tren) has been designed, synthesized and established as a chemosensor for ATP over ADP, AMP and a series of other anions in aqueous CH3CN at pH 6.5. Compound 1 exhibits a significant change in emission upon complexation of ATP. In CH3CN, the sensor selectively binds H2PO4- and forms an excimer with significant intensity. Furthermore, the intracellular ATP detection using 1 was possible through fluorescent confocal imaging.
- Ghosh, Kumaresh,Tarafdar, Debojyoti,Samadder, Asmita,Khuda-Bukhsh, Anisur Rahman
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- Synthesis and characterization of 3-O-esters of N-acetyl-D-glucosamine derivatives as organogelators
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Carbohydrate derived low molecular weight organogelators are interesting compounds with many potential applications. Selective functionalization of the different hydroxyl substituents on d-glucose and d-glucosamine resulted in small molecular gelators. Previously we have found that the C-2 acylated derivatives including esters and carbamates of 4,6-O-benzylidene protected glucose and glucosamine derivatives have shown remarkable applications as molecular gelators. In this research, in order to probe the structural influence of sugar derivatives on molecular self-assembly, we introduced acylation functional groups to the 3-hydroxyl group of 4,6-O-benzylidene acetal protected N-acetyl glucosamine derivatives. A library of fourteen ester derivatives was synthesized and characterized. The ester derivatives typically formed gels in pump oil and aqueous mixtures of dimethyl sulfoxide or ethanol. The resulting gels were characterized using optical microscopy, and rheology, etc. All alkyl ester derivatives were gelators for pump oil. A short chain ester derivative was able to form gels in a few different oils and the corresponding oil water mixtures phase selectively. The compound was also used to trap naproxen sodium and formed a stable co-gel. The controlled release of the drug from the gel to the aqueous phase was analyzed using UV-vis spectroscopy. These results show that the functionalization at the 3-OH position of the N-acetyl glucosamine derivative is a feasible strategy in designing new classes of organogelators.
- Chen, Anji,Samankumara, Lalith P.,Garcia, Consuelo,Bashaw, Kristen,Wang, Guijun
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- Annelated Pyridine Bases for the Selective Acylation of 1,2-Diols
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A set of 24 annelated derivatives of 4-diaminopyridine (DMAP) has been synthesized and tested with respect to its catalytic potential in the regioselective acylation of 1,2-diol substrates. The Lewis basicities of the catalysts as quantified through quantum chemical calculations vary due to inductive substituent effects and intramolecular stacking interactions between side chain π-systems and the pyridinium core ring system. The primary over secondary hydroxyl group selectivities in catalytic acylations of 1,2-diol substrates depend on the size and the steric demand of the Lewis base and the anhydride reagent.
- Mayr, Stefanie,Zipse, Hendrik
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supporting information
(2022/03/08)
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- Novel Pyridine-Based Hydroxamates and 2′-Aminoanilides as Histone Deacetylase Inhibitors: Biochemical Profile and Anticancer Activity
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Starting from the N-hydroxy-3-(4-(2-phenylbutanoyl)amino)phenyl)acrylamide (5 b) previously described by us as a HDAC inhibitor, we prepared four aza-analogues, 6–8, 9 b, as regioisomers containing the pyridine nucleus. Preliminary screening against mHDAC1 highlighted the N-hydroxy-5-(2-(2-phenylbutanoyl)amino)pyridyl)acrylamide (9 b) as the most potent inhibitor. Thus, we further developed both pyridylacrylic- and nicotinic-based hydroxamates (9 a, 9 c–f, and 11 a–f) and 2′-aminoanilides (10 a–f and 12 a–f), related to 9 b, to be tested against HDACs. Among them, the nicotinic hydroxamate 11 d displayed sub-nanomolar potency (IC50: 0.5 nM) and selectivity up to 34 000 times that of HDAC4 and from 100 to 1300 times that of all the other tested HDAC isoforms. The 2′-aminoanilides were class I-selective HDAC inhibitors, generally more potent against HDAC3, with the nicotinic anilide 12 d being the most effective (IC50HDAC3=0.113 μM). When tested in U937 leukemia cells, the hydroxamates 9 e, 11 c, and 11 d blocked over 80 % of cells in G2/M phase, whereas the anilides did not alter cell-cycle progress. In the same cell line, the hydroxamate 11 c and the anilide 10 b induced about 30 % apoptosis, and the anilide 12 c displayed about 40 % cytodifferentiation. Finally, the most potent compounds in leukemia cells 9 b, 11 c, 10 b, 10 e, and 12 c were also tested in K562, HCT116, and A549 cancer cells, displaying antiproliferative IC50 values at single-digit to sub-micromolar level.
- Zwergel, Clemens,Di Bello, Elisabetta,Fioravanti, Rossella,Conte, Mariarosaria,Nebbioso, Angela,Mazzone, Roberta,Brosch, Gerald,Mercurio, Ciro,Varasi, Mario,Altucci, Lucia,Valente, Sergio,Mai, Antonello
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p. 989 - 999
(2020/12/17)
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- N-Alkenylation of hydroxamic acid derivatives with ethynyl benziodoxolone to synthesizecis-enamides through vinyl benziodoxolones
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The stereoselective synthesis ofcis-β-N-alkoxyamidevinyl benziodoxolones (cis-β-N-RO-amide-VBXs) fromO-alkyl hydroxamic acids in the presence of an ethynyl benziodoxolone-acetonitrile complex (EBX-MeCN) is reported herein. The reaction was performed under mild conditions including an aqueous solvent, a mild base, and room temperature. The reaction tolerated variousO-alkyl hydroxamic acids derived from carboxylic acids, such as amino acids, pharmaceuticals, and natural products. Vinyl dideuteratedcis-β-N-MeO-amide-VBXs were also synthesized using deuterium oxide as the deuterium source. Valine-derivedcis-β-N-MeO-amide-VBX was stereospecifically derivatized to hydroxamic acid-derivedcis-enamides without the loss of stereoselectivity or reduction in the deuterium/hydrogen ratio.
- Shimbo, Daisuke,Maruyama, Toshifumi,Tada, Norihiro,Itoh, Akichika
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supporting information
p. 2442 - 2447
(2021/04/02)
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- Benzoic acid derivative as well as preparation method and medicinal application thereof
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The invention discloses a benzoic acid derivative as well as a preparation method and a pharmaceutical application thereof, and belongs to the technical field of medicines. The invention specifically discloses a benzoic acid derivative represented by a co
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Paragraph 0193-0197
(2021/09/21)
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- Hydrosilylative reduction of primary amides to primary amines catalyzed by a terminal [Ni-OH] complex
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A terminal [Ni-OH] complex1, supported by triflamide-functionalized NHC ligands, catalyzes the hydrosilylative reduction of a range of primary amides into primary amines in good to excellent yields under base-free conditions with key functional group tolerance. Catalyst1is also effective for the reduction of a variety of tertiary and secondary amides. In contrast to literature reports, the reactivity of1towards amide reduction follows an inverse trend,i.e., 1° amide > 3° amide > 2° amide. The reaction does not follow a usual dehydration pathway.
- Pandey, Pragati,Bera, Jitendra K.
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supporting information
p. 9204 - 9207
(2021/09/20)
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- The Importance of 1,5-Oxygen???Chalcogen Interactions in Enantioselective Isochalcogenourea Catalysis
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The importance of 1,5-O???chalcogen (Ch) interactions in isochalcogenourea catalysis (Ch=O, S, Se) is investigated. Conformational analyses of N-acyl isochalcogenouronium species and comparison with kinetic data demonstrate the significance of 1,5-O???Ch interactions in enantioselective catalysis. Importantly, the selenium analogue demonstrates enhanced rate and selectivity profiles across a range of reaction processes including nitronate conjugate addition and formal [4+2] cycloadditions. A gram-scale synthesis of the most active selenium analogue was developed using a previously unreported seleno-Hugerschoff reaction, allowing the challenging kinetic resolutions of tertiary alcohols to be performed at 500 ppm catalyst loading. Density functional theory (DFT) and natural bond orbital (NBO) calculations support the role of orbital delocalization (occurring by intramolecular chalcogen bonding) in determining the conformation, equilibrium population, and reactivity of N-acylated intermediates.
- Cockroft, Scott L.,Elmi, Alex,Frost, Aileen B.,Ling, Kenneth B.,McLaughlin, Calum,Morris, Rylie K.,Pascoe, Dominic J.,Slawin, Alexandra M. Z.,Smith, Andrew D.,Smith, Terry K.,Willoughby, Patrick H.,Woods, Andrew M.,Young, Claire M.,de la Houpliere, Alix
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supporting information
p. 3705 - 3710
(2020/02/11)
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- N-monoarylacetothioureas as potent urease inhibitors: synthesis, SAR, and biological evaluation
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A urease inhibitor with good in vivo profile is considered as an alternative agent for treating infections caused by urease-producing bacteria such as Helicobacter pylori. Here, we report a series of N-monosubstituted thioureas, which act as effective urease inhibitors with very low cytotoxicity. One compound (b19) was evaluated in detail and shows promising features for further development as an agent to treat H. pylori caused diseases. Excellent values for the inhibition of b19 against both extracted urease and urease in intact cell were observed, which shows IC50 values of 0.16 ± 0.05 and 3.86 ± 0.10 μM, being 170- and 44-fold more potent than the clinically used drug AHA, respectively. Docking simulations suggested that the monosubstituted thiourea moiety penetrates urea binding site. In addition, b19 is a rapid and reversible urease inhibitor, and displays nM affinity to urease with very slow dissociation (koff=1.60 × 10?3 s?1) from the catalytic domain.
- Fang, Hai-Lian,He, Jie-Ling,Li, Wei-Yi,Liu, Shan-Shan,Ni, Wei-Wei,Pan, Xing-Ming,Xiao, Zhu-Ping,Ye, Ya-Xi,Yi, Juan,Zhou, Mi,Zhou, Tian-Li,Zhu, Hai-Liang
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p. 404 - 413
(2020/01/03)
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- Palladium-Catalyzed 2-(Neopentylsulfinyl)aniline Directed C–H Acetoxylation and Alkenylation of Arylacetamides
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The 2-(neopentylsulfinyl)aniline directing group that promotes rapid palladium-catalyzed C–H acetoxylation and alkenylation of arylacetamides has been developed. The acetoxylation reaches completion within only 40 min at 100 °C and leads to the bis-functionalized products. Alternatively, the reaction can be carried out at room temperature, which is beneficial for sensitive substrates. For the alkenylation, we have developed a protocol in which easily available 1-substituted cyclopropanols were employed as equivalents of vinyl ketones.
- Barysevich, Maryia V.,Laktsevich-Iskryk, Marharyta V.,Krech, Anastasiya V.,Zhabinskii, Vladimir N.,Khripach, Vladimir A.,Hurski, Alaksiej L.
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supporting information
p. 937 - 943
(2020/02/25)
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- Propargylamine-selective dual fluorescence turn-on method for post-synthetic labeling of DNA
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We have developed a propargylamine-selective dual fluorescence turn-on system, using ylidenemalononitrile enamines, for post-synthetic DNA labeling, allowing the direct monitoring of DNA using dual emission in living cells.
- Nguyen, Van Thang,Pandith, Anup,Seo, Young Jun
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supporting information
p. 3199 - 3202
(2020/03/23)
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- One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles
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We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C-H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target. This journal is
- Bobal, Pavel,Otevrel, Jan,Svestka, David
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p. 25029 - 25045
(2020/07/14)
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- Synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarinviaa TsOH-mediated tandem reaction
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A concise and efficient method for the synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarin using available 1-(2-hydroxyphenyl)-2-phenylethanone and Meldrum's acid has been developed. This transformation involved a tandem aldol reaction/lactonization/Friedel-Crafts reaction to form a lactone ring and a benzene ring. It showed high atom economy with water and acetone as the byproducts. Mechanism studies demonstrated two roles of Meldrum's acid: (i) as the reagent for the tandem reaction, and (ii) as the catalyst for the Friedel-Crafts reaction. Moreover, the hydroxyl group of 7-hydroxy-6H-naphtho[2,3-c]coumarin was further functionalized efficiently by arylethynyl, aryl, and cyano groups to furnish D-π-A compounds with excellent fluorescence emissions (ΦF= 0.14-0.78).
- Li, Chenyu,Liang, Yong,Ma, Zhishuang,Wang, Ding,Wang, Nana,Wang, Tao,Zhang, Zunting
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supporting information
p. 10369 - 10372
(2020/09/16)
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- Palladium-Catalyzed Distal C?H Selenylation of 2-Aryl Acetamides with Diselenides and Selenyl Chlorides
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A convenient and effective method of palladium-catalyzed C?H selenylation of the 2-aryl acetamides assisted with removable 8-aminoquinoline with readily available diselenides and selenyl chlorides has been developed. This selenylation reaction is scalable and tolerates a wide range of functional groups, providing a straightforward way of the preparing unsymmetrical diaryl selenides and dibenzoselene-pinone. Preliminary mechanistic studies indicated that a single-electron transfer type mechanism and facile C?H metalation are operative. (Figure presented.).
- Gu, Linghui,He, Meicui,Ma, Wenbo,Tan, Yuqiang,Wang, Yang,Wang, Yuchi,Zhang, Chunran
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supporting information
p. 5708 - 5715
(2020/12/01)
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- Cobalt(II)-Catalyzed Stereoselective Olefin Isomerization: Facile Access to Acyclic Trisubstituted Alkenes
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Stereoselective synthesis of trisubstituted alkenes is a long-standing challenge in organic chemistry, due to the small energy differences between E and Z isomers of trisubstituted alkenes (compared with 1,2-disubstituted alkenes). Transition metal-catalyzed isomerization of 1,1-disubstituted alkenes can serve as an alternative approach to trisubstituted alkenes, but it remains underdeveloped owing to issues relating to reaction efficiency and stereoselectivity. Here we show that a novel cobalt catalyst can overcome these challenges to provide an efficient and stereoselective access to a broad range of trisubstituted alkenes. This protocol is compatible with both mono- and dienes and exhibits a good functional group tolerance and scalability. Moreover, it has proven to be a useful tool to construct organic luminophores and a deuterated trisubstituted alkene. A preliminary study of the mechanism suggests that a cobalt-hydride pathway is involved in the reaction. The high stereoselectivity of the reaction is attributed to both a π-πstacking effect and the steric hindrance between substrate and catalyst.
- Zhang, Sheng,Bedi, Deepika,Cheng, Lu,Unruh, Daniel K.,Li, Guigen,Findlater, Michael
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supporting information
p. 8910 - 8917
(2020/12/23)
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- CEPHALOSPORIN CIPROFLOXACIN HYBRID COMPOUNDS
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A compound of formula (Ia) and related aspects.
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Page/Page column 35; 39; 47
(2020/06/05)
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- Synthesis and bioactivities of diamide derivatives containing a phenazine-1-carboxamide scaffold
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Taking natural product phenazine-1-carboxamide (PCN) as a lead compound, a series of novel phenazine-1-carboxylic acid diamide derivatives were designed and synthesised. Their structures were confirmed by 1H-NMR and HRMS. The bioassays showed that some of the target compounds exhibited promising in vitro fungicidal activities, and exhibited excellent and selective herbicidal activities. Particularly, compounds c, h, o and s displayed root length inhibition activities against barnyard grass with the rate of more than 80%. Compound c exhibited the best activity among all the target compounds against barnyard grass stalk length with the IC50 value of 0.158?mmol/L, and compound o exhibited the best and wide spectrum inhibition against barnyard grass root length and rape in both root length and stalk length herbicidal activities with its IC50 values of 0.067, 0.048 and 0.059?mmol/L respectively. The analysis of preliminary Structure-Activity Relationships provides the theoretical basis for further design of phenazine-1-carboxylic acid.
- Zhu, Xiang,Zhang, Min,Yu, Linhua,Xu, Zhihong,Yang, Dan,Du, Xiaoying,Wu, Qinglai,Li, Junkai
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supporting information
p. 2453 - 2460
(2018/03/29)
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- D-AMINO ACID OXIDASE INHIBITORS AND THERAPEUTIC USES THEREOF
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The present invention relates to compounds of Formula (I): or a pharmaceutically acceptable salt thereof, wherein: each of A, B, C, D, and E, independently, is C, N, N—H, O, S, or absent is a single bond or a double bond; each of X, Y, and Z, independentl
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Paragraph 0175
(2019/04/29)
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- Directed Remote Lateral Metalation: Highly Substituted 2-Naphthols and BINOLs by In Situ Generation of a Directing Group
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A general synthesis of highly substituted 2-naphthols based on a new carbanionic reaction sequence is demonstrated. The reaction exploits the dual nature of lithium bases consisting of consecutive ring opening of readily available coumarins with either LiNEt2 or LiNiPr2 into Z-cinnamamides, thus generating a directing group in situ and allowing, by conformational freedom, a lateral directed remote metalation for ring closure to give the aryl 2-naphthols in good to excellent yields. These transformations can be combined to provide a more efficient one-pot process. Mechanistic insight into the remote lateral metalation step, demonstrating the requirement of Z-cinnamamide, is described. Application of this methodology to the synthesis of highly substituted 3,3′-diaryl BINOL ligands is also reported.
- Patel, Jignesh J.,Laars, Marju,Gan, Wei,Board, Johnathan,Kitching, Matthew O.,Snieckus, Victor
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supporting information
p. 9425 - 9429
(2018/07/29)
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- Synthesis and insecticidal activity of rotenone analogues
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Rotenone, one of traditional botanical insecticide, has been used more than one hundred years. A variety of rotenone derivatives were designed and synthesized in recent years due to environmental benign character and not easy to generate insecticide resistance. This paper described the molecular design, synthesis, and insecticidal activities of a series of rotenone analogues and 2-substituted rotenone derivatives. The preliminary bioassay showed that isorotenone and 2-rotenone nicotinate is equal to rotenone's against Musca domestica.
- Zhicheng, Liu,Dingxin, Jiang,Hanhong, Xu,Xiaohua, Zheng
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p. 1063 - 1070
(2018/10/26)
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- Pd-Catalyzed Decarbonylative Cross-Couplings of Aroyl Chlorides
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This report describes a method for Pd-catalyzed decarbonylative cross-coupling that enables the conversion of carboxylic acid derivatives to biaryls, aryl amines, aryl ethers, aryl sulfides, aryl boronate esters, and trifluoromethylated arenes. The success of this transformation leverages the Pd0/Brettphos-catalyzed decarbonylative chlorination of aroyl chlorides, which can then participate in diverse cross-coupling reactions in situ using the same Pd catalyst.
- Malapit, Christian A.,Ichiishi, Naoko,Sanford, Melanie S.
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supporting information
p. 4142 - 4145
(2017/08/15)
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- 6-aminopurine ethyl-naphthylacetic acid ester compound and application thereof as plant growth regulator
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The invention discloses a 6-aminopurine ethyl-naphthylacetic acid ester compound which serves as a plant growth regulator. The compound shown as the formula I has excellent effects of promoting germination and rooting, increasing the yield and improving the quality and can be widely used for increasing the yield or improving the survival rate in agriculture or forestry.
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Paragraph 0020; 0021; 0022
(2017/07/21)
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- Naphthylacetic acid naphthalimide ester compound and application thereof
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The invention discloses a naphthylacetic acid naphthalimide ester compound of which the structure is as shown in a formula I. The naphthylacetic acid naphthalimide ester compound is used as a plant growth regulator. The compound in the formula I has excellent germination-accelerating effect, root-inducing effect and production-increasing and quality-improving effects, has a good sterilization effect, especially has a control effect on wheat sharp eyespot, phytoph-thora capsici leonian and apple ring rot at 200ppm, and can be widely applied to disease prevention and production increase in agriculture or forestry.
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Paragraph 0017-0020
(2017/07/20)
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- Chemoselectivity in Esterification Reactions - Size Matters after All
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The reaction of carboxylic acid chlorides with secondary alcohols carrying either flexible alkyl or rigid aryl substituents was studied through a series of competition experiments. Aliphatic acid chlorides react preferentially with the aryl-substituted alcohols, while acid chlorides derived from aromatic carboxylic acids react with very low selectivity. Catalysis by 9-azajulolidine (TCAP) increases the selectivity strongly, while solvent and temperature effects are only moderate. The size of the alcohol substituents seems to impact selectivities only for rigid aryl substituents, and highest selectivities have been found for 1-(1-pyrenyl)ethanol.
- Helberg, Julian,Marin-Luna, Marta,Zipse, Hendrik
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supporting information
p. 3460 - 3470
(2017/07/27)
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- Development of catalytic deacylative alkylations (DaA) of 3-acyl-2-oxindoles: total synthesis of meso-chimonanthine and related alkaloids
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We present an effective deacylative alkylation strategy for the construction of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position. A wide variety of products with quaternary centers could be accessed by employing simple Pd(0) catalysis under mild reaction conditions. Importantly, the same strategy works equally well for the dimeric 2-oxindole system, furnishing products with a vicinal quaternary center in favour of meso-isomer as the major product. Eventual application to the total syntheses of meso-chimonanthine and meso-folicanthine very well demonstrates the synthetic potential of this strategy.
- Kumar, Nivesh,Das, Mrinal Kanti,Ghosh, Santanu,Bisai, Alakesh
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supporting information
p. 2170 - 2173
(2017/02/19)
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- Development of [18F]Maleimide-Based Glycogen Synthase Kinase-3β Ligands for Positron Emission Tomography Imaging
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Dysregulation of glycogen synthase kinase-3β (GSK-3β) is implicated in the pathogenesis of neurodegenerative and psychiatric disorders. Thus, development of GSK-3β radiotracers for positron emission tomography (PET) imaging is of paramount importance, because such a noninvasive imaging technique would allow better understanding of the link between the activity of GSK-3β and central nervous system disorders in living organisms, and it would enable early detection of the enzyme’s aberrant activity. Herein, we report the synthesis and biological evaluation of a series of fluorine-substituted maleimide derivatives that are high-affinity GSK-3β inhibitors. Radiosynthesis of a potential GSK-3β tracer [18F]10a is achieved. Preliminary in vivo PET imaging studies in rodents show moderate brain uptake, although no saturable binding was observed in the brain. Further refinement of the lead scaffold to develop potent [18F]-labeled GSK-3 radiotracers for PET imaging of the central nervous system is warranted.
- Hu, Kongzhen,Patnaik, Debasis,Collier, Thomas Lee,Lee, Katarzyna N.,Gao, Han,Swoyer, Matthew R.,Rotstein, Benjamin H.,Krishnan, Hema S.,Liang, Steven H.,Wang, Jin,Yan, Zhiqiang,Hooker, Jacob M.,Vasdev, Neil,Haggarty, Stephen J.,Ngai, Ming-Yu
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supporting information
p. 287 - 292
(2017/03/17)
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- Discovery of a potent protein kinase D inhibitor: insights in the binding mode of pyrazolo[3,4-d]pyrimidine analogues
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In this study, we set out to rationally optimize PKD inhibitors based on the pyrazolo[3,4-d]pyrimidine scaffold. The lead compound for this study was 1-NM-PP1, which was previously found by us and others to inhibit PKD. In our screening we identified one compound (3-IN-PP1) displaying a 10-fold increase in potency over 1-NM-PP1, opening new possibilities for specific protein kinase inhibitors for kinases that show sensitivity towards pyrazolo[3,4-d]pyrimidine derived compounds. Interestingly the observed SAR was not in complete agreement with the commonly observed binding mode where the pyrazolo[3,4-d]pyrimidine compounds are bound in a similar fashion as PKD's natural ligand ATP. Therefore we suggest an alternate binding mode where the compounds are flipped 180 degrees. This possible alternate binding mode for pyrazolo[3,4-d]pyrimidine based compounds could pave the way for a new class of specific protein kinase inhibitors for kinases sensitive towards pyrazolo[3,4-d]pyrmidines.
- Verschueren, Klaas,Cobbaut, Mathias,Demaerel, Joachim,Saadah, Lina,Voet, Arnout R. D.,Van Lint, Johan,De Borggraeve, Wim M.
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p. 640 - 646
(2017/03/30)
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- Carboxamides as N-Alkylating Reagents of Secondary Amines in Indium-Catalyzed Reductive Amination with a Hydrosilane
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A method for the catalytic reductive N-alkylation of amines by using secondary amides as the alkyl source was developed. A versatile type of carboxamide functioned as an N-alkylation reagent in the presence of an indium(III) catalyst and a hydrosilane to provide alkylated tertiary amines efficiently. This amide-based catalytic N-alkylation strategy is considered to be a highly useful protocol to access unsymmetrical tertiary amines.
- Ogiwara, Yohei,Shimoda, Wataru,Ide, Keisuke,Nakajima, Takumi,Sakai, Norio
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supporting information
p. 2866 - 2870
(2017/06/06)
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- Synthesis of gibberellic acid derivatives and their effects on plant growth
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A series of novel C-3-OH substituted gibberellin derivatives bearing an amide group were designed and synthesized from the natural product gibberellic acid (GA3). Their activities on the plant growth regulation of rice and Arabidopsis were evaluated in vivo. Among these compounds, 10d and 10f exhibited appreciable inhibitory activities on rice (48.6% at 100 μmol/L) and Arabidopsis (41.4% at 100mol/L), respectively. These results provide new insights into the design and synthesis of potential plant growth regulators.
- Tian, Hao,Xu, Yiren,Liu, Shaojin,Jin, Dingsha,Zhang, Jianjun,Duan, Liusheng,Tan, Weiming
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- C-H and N-H Bond Annulation of Benzamides with Isonitriles Catalyzed by Cobalt(III)
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A simple efficient, atom-economical procedure was developed for the cobalt-catalyzed C-H bond annulation of benzamides with isonitriles under mild conditions. The reaction tolerates a variety of functional group including heterocycles. Diverse 3-(alkylimino)-2-quinolin-8-yl-2,3-dihydro-1 H -isoindol-1-ones were synthesized using isonitriles as the C1 source through C-H and N-H bond annulation via C-H bond activation in a 'green' solvent. Vinylamides were also used similarly with tert -butyl isonitrile to give 3-(tert -butylimino)-1-quinolin-8-yl-1 H -pyrrol-2(5 H)-ones.
- Kalsi, Deepti,Barsu, Nagaraju,Dahiya, Pardeep,Sundararaju, Basker
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supporting information
p. 3937 - 3944
(2017/08/29)
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- Stereoselective synthesis of Z-vinylsilanes via palladium-catalyzed direct intermolecular silylation of C(sp2)-H bonds
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An efficient and convenient palladium-catalyzed direct intermolecular silylation of C(sp2)-H bonds by using disilanes as the silicon source with the assistance of a readily removable bidentate directing group is reported. This strategy provided a regio- and stereoselective protocol for exclusive synthesis of Z-vinylsilanes with reasonable to excellent yields and good functional group compatibility. Silylation of the isolated palladacycle intermediate revealed the Z-stereoselective pathway. Moreover, the practicality and effectiveness of this method were illustrated by a gram-scale experiment and further functionalization of the silylation product.
- Pan, Jin-Long,Chen, Chao,Ma, Zhi-Gang,Zhou, Jia,Wang, Li-Ren,Zhang, Shu-Yu
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supporting information
p. 5216 - 5219
(2017/11/06)
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- Naphthalenedicarboxamide ethylnaphthalene acetic ester type compound and application thereof
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The invention discloses an Naphthalenedicarboxamide ethylnaphthalene acetic ester type compound with the structure shown as the formula I and a purpose of the compound as a plant growth regulator. The compound shown as the formula I shown as the accompanying drawing has excellent plant growth regulation activity of promoting rooting, increasing the yield and improving the quality; by the modes of seed treatment or root and stem leaf spraying and the like, the compound can be widely applied to rooting, seeding strengthening, yield increase and quality improvement of plants or crops such as grains, cotton, fruit and vegetables, and has the characteristics of use safety, low cost, obvious effect and the like.
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Paragraph 0021; 0022; 0023
(2016/10/08)
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- Synthesis of Unsymmetrical Diaryl Acetamides, Benzofurans, Benzophenones, and Xanthenes by Transition-Metal-Free Oxidative Cross-Coupling of sp3 and sp2 C-H Bonds
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A chemo- and regioselective intermolecular sp3 C-H and sp2 C-H coupling reaction for C-C bond formation is described to access unsymmetrical diaryl acetamides under TM-free conditions from sec- and tert-arylacetamides and nitroarenes using tert-butoxide base in DMSO at room temperature. The coupling partners with sensitive functionalities such as chloro, bromo, hydroxy, and cyano were also amenable to the developed reaction. Synthesized α-(2/4-nitroaryl) phenylacetamides have been transformed into biologically important benzofurans, xanthenes, diaryl indoles, and unsymmetrical benzophenones by novel routes without applying a transition metal. Overall, an economical, yet efficient, strategy has been devised to access unsymmetrical diarylacetamides with the possibility of their further elaboration into a variety of biologically important heterocycles. Mechanistic understanding suggests that the reaction proceeds by a nucleophilic addition of a phenylacetamide carbanion, which is generated in the presence of tert-butoxide base, to the para or ortho (if para is substituted) position of nitrobenzene. The formed α-(4-nitrocyclohexa-2,4-dien-1-yl) phenylacetamide anion intermediate oxidized by a basic solution of DMSO or atmospheric oxygen led to the desired sp3 C-H and sp2 C-H coupled α-(2/4-nitroaryl) phenylacetamides.
- Rathore, Vandana,Sattar, Moh.,Kumar, Raushan,Kumar, Sangit
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p. 9206 - 9218
(2016/10/14)
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- A naphthylacetic acid pyridine ethyl ester compound and use thereof (by machine translation)
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The invention discloses a structure as shown in formula I the naphthylacetic acid pyridine ethyl ester compound and its salt: The salt is inorganic acid salt or organic acid salt. The compounds of formula I and its salt has excellent plant growth regulating activity, can be used alone or with other active component composite use, is used for improving crop yield. (by machine translation)
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Paragraph 0025; 0026; 0027; 0028
(2016/10/27)
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- An amidation/cyclization approach to the synthesis of N-hydroxyquinolinones and their biological evaluation as potential anti-plasmodial, anti-bacterial, and iron(II)-chelating agents
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A 26-member library of novel N-hydroxyquinolinone derivatives was synthesized by a one-pot Buchwald-type palladium catalyzed amidation and condensation sequence. The design of these rare scaffolds was inspired from N-hydroxypyridones and 2-quinolinones classes of compounds which have been shown to have rich biological activities. The synthesized compounds were evaluated for their anti-plasmodial and anti-bacterial properties. In addition, these compounds were screened for their iron(II)-chelation properties. Notably, four of these compounds exhibited anti-plasmodial activities comparable to that of the natural product cordypyridone B.
- Teng, Yanbo,Suwanarusk, Rossarin,Ngai, Mun Hong,Srinivasan, Rajavel,Ong, Alice Soh Meoy,Ho, Bow,Rnia, Laurent,Chai, Christina L.L.
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supporting information
p. 607 - 610
(2015/01/30)
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- Pd(OAc)2-catalyzed lactonization of arylacetamides involving oxidation of C-H bonds
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The reaction of arylacetamides that contain a quinolin-8-ylmethylamine as the directing group with PhI(OAc)2, in the presence of Pd(OAc)2 as the catalyst, results in lactonization to give γ-lactones, the formation of which involves activation of the ortho C-H bonds, with concomitant cleavage of the directing group.
- Uemura, Takeshi,Igarashi, Takuya,Noguchi, Moe,Shibata, Kaname,Chatani, Naoto
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supporting information
p. 621 - 623
(2015/05/20)
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- Carboxylate Assisted Ni-Catalyzed C-H Bond Allylation of Benzamides
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A one-step synthetic method was developed for allylation of benzamides using Ni(COD)2/RCO2H and [Ni(μ-H2O)(OOCCMe3)2(HOOCCMe3)2]2 (A′) catalytic system. Efficient, well-defined, air and moisture-stable Ni-pivalate complex was isolated and employed in catalytic allylation. The influence of solvent on product selectivity was also investigated. Nickel-back: A one-step synthetic method was developed for the allylation of benzamides using in situ formed nickel carboxylate Ni(COD)2/RCO2H catalyst (see scheme). The air and moisture stable Ni-pivalate complex was isolated and employed in catalytic allylation. The influence of solvent on product selectivity is discussed.
- Barsu, Nagaraju,Kalsi, Deepti,Sundararaju, Basker
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supporting information
p. 9364 - 9368
(2015/06/30)
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- Ligand-Enabled Meta-C-H Alkylation and Arylation Using a Modified Norbornene
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2-Carbomethoxynorbornene is identified as a more effective transient mediator to promote a Pd(II)-catalyzed meta-C(sp2)-H alkylation of amides with various alkyl iodides as well as arylation with previously incompatible aryl iodides. The use of a tailor-made quinoline ligand is also crucial for this reaction to proceed.
- Shen, Peng-Xiang,Wang, Xiao-Chen,Wang, Peng,Zhu, Ru-Yi,Yu, Jin-Quan
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supporting information
p. 11574 - 11577
(2015/09/28)
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- PLANT GROWTH REGULATOR COMPRISING COMPOUND HAVING SUBSTITUENT COORDINATING TO ZINC
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PROBLEM TO BE SOLVED: To provide a plant growth regulator having a more reduced risk of withering plants and to provide a simple plant growth regulating method. SOLUTION: Provided is a plant growth regulator that comprises, as an active ingredient, a compound or agriculturally acceptable salt, hydrate or solvate thereof in which the terminal carboxyl group in an indole or naphthalene compound having carboxy alkyl group is made to be a group or analog thereof derived from hydroxamic acid capable of coordinating to zinc. COPYRIGHT: (C)2015,JPOandINPIT
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Paragraph 0146; 0147; 0152-0154; 0159-0161; 0162-0164
(2018/10/31)
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- 4-Hydroxy-3-(naphthalen-1-ylmethyl)thiophen-2(5H)-one as inhibitors of tyrosyl-tRNA synthase: Synthesis, molecular docking and antibacterial evaluation
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A series of novel 4-hydroxy-3-(naphthalen-1-ylmethyl)thiophen-2(5H)-ones as tyrosyl-tRNA synthetase inhibitors were synthesized. Of these compounds, 4-(naphthalen-1-ylmethyl)-5-oxo-2,5-dihydrothiophen-3-yl-2-(4-hydroxyphenyl) acetate (29) was the most potent. The binding model and structure-activity relationship indicate that replacement of phenyl acetate in the side chain of 29 with a substituent containing more hydrophilic groups would be more suitable for further modification. Antibacterial assay revealed that the synthetic compounds are effective against growth of Gram-positive organisms, and 29 is the most potent agent against Staphylococcus aureus ATCC 25923 with MIC 50 value of 0.21 μg/mL.
- Sun, Juan,Liu, Jia-Jia,Zhou, Wei,Guo, Feng-Jiao,Wang, Xin-Yi,Zhu, Hai-Liang
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p. 104 - 109
(2013/11/19)
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- HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF
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Provided herein are heterocyclyl compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or management of various neurological disorders, including but not limited to, psychosis and schizophrenia.
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Paragraph 00373
(2014/07/21)
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- Ylidenemalononitrile enamines as fluorescent "turn-on" indicators for primary amines
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Ylidenemalononitrile enamines undergo rapid amine exchange followed by a cyclization with primary amines to yield fluorescent products with emission intensities as high as 900 times greater than the starting materials. After identifying the fluorescent species by X-ray crystallography, we demonstrate that the rate of amine exchange is substrate dependent and that by simple structural variation the fluorescence can be tuned over the entire visible spectrum. We further demonstrate their potential application in biomolecule labeling.
- Longstreet, Ashley R.,Jo, Minyoung,Chandler, Rebecca R.,Hanson, Kenneth,Zhan, Naiqian,Hrudka, Jeremy J.,Mattoussi, Hedi,Shatruk, Michael,McQuade, D. Tyler
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supporting information
p. 15493 - 15496
(2015/01/08)
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- The iso-VAPOL ligand: Synthesis, solid-state structure and its evaluation as a BOROX catalyst
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The new vaulted biaryl ligand iso-VAPOL is an isomer of VAPOL but has the chiral pocket of VANOL. The synthesis of iso-VAPOL involves a cycloaddition/electrocyclization cascade (CAEC) similar to one that is used for VAPOL except that the starting material
- Gupta, Anil K.,Zhang, Xin,Staples, Richard J.,Wulff, William D.
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p. 4406 - 4415
(2015/02/02)
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- Palladium-catalyzed aryl C-H olefination with unactivated, aliphatic alkenes
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Palladium-catalyzed coupling between aryl halides and alkenes (Mizoroki-Heck reaction) is one of the most popular reactions for synthesizing complex organic molecules. The limited availability, problematic synthesis, and higher cost of aryl halide precursors (or their equivalents) have encouraged exploration of direct olefination of aryl carbon-hydrogen (C-H) bonds (Fujiwara-Moritani reaction). Despite significant progress, the restricted substrate scope, in particular noncompliance of unactivated aliphatic olefins, has discouraged the use of this greener alternative. Overcoming this serious limitation, we report here a palladium-catalyzed chelation-assisted ortho C-H bond olefination of phenylacetic acid derivatives with unactivated, aliphatic alkenes in good to excellent yields with high regio- and stereoselectivities. The versatility of this operationally simple method has been demonstrated through drug diversification and sequential C-H olefination for synthesizing divinylbenzene derivatives.
- Deb, Arghya,Bag, Sukdev,Kancherla, Rajesh,Maiti, Debabrata
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supporting information
p. 13602 - 13605
(2015/02/05)
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- Design, synthesis and insecticidal activity of novel anthranilic diamides with benzyl sulfide scaffold
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A series of novel anthranilic diamides with benzyl sulfide scaffold were synthesized, in which N-pyridylpyrazole moiety generally regarded as key pharmacophore was abandoned. The target compounds were characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. The preliminary bioassays indicated that half of the title compounds were endowed with good insecticidal activities against armyworm (Mythimna sepatara) at the concentration of 500 mg/L. Exhilaratingly, the synthesized compound 3a was also active against Tetranychus cinnabarinus at 100 mg/L. The difference in activities between the target compounds was influenced by the substituents, which provided some hints for further investigation on structure modifications.
- Chen, Yin-Bo,Li, Ji-Ling,Shao, Xu-Sheng,Xu, Xiao-Yong,Li, Zhong
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p. 673 - 676
(2013/07/26)
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- Colorimeric and fluorescence ON-OFF probe for acetate anion based on thiourea derivative: Theory and experiment
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Based on thiourea moiety, three colorimetric and fluorescent anion probes have been synthesized. Results indicated the probe 1 containing p-NO2 group showed the strongest binding ability for AcO- among the anions tested (F-/sup
- Shang, Xuefang,Tian, Shuanbao,Xi, Nankai,Li, Yue,Liang, Dong,Liu, Yun,Yin, Zhenya,Zhang, Jinlian,Xu, Xiufang
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supporting information
p. 276 - 281
(2013/03/14)
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- The human Aurora kinase inhibitor danusertib is a lead compound for anti-trypanosomal drug discovery via target repurposing
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New drugs for neglected tropical diseases such as human African trypanosomiasis (HAT) are needed, yet drug discovery efforts are not often focused on this area due to cost. Target repurposing, achieved by the matching of essential parasite enzymes to those human enzymes that have been successfully inhibited by small molecule drugs, provides an attractive means by which new drug optimization programs can be pragmatically initiated. In this report we describe our results in repurposing an established class of human Aurora kinase inhibitors, typified by danusertib (1), which we have observed to be an inhibitor of trypanosomal Aurora kinase 1 (TbAUK1) and effective in parasite killing in vitro. Informed by homology modeling and docking, a series of analogs of 1 were prepared that explored the scope of the chemotype and provided a nearly 25-fold improvement in cellular selectivity for parasite cells over human cells.
- Ochiana, Stefan O.,Pandarinath, Vidya,Wang, Zhouxi,Kapoor, Rishika,Ondrechen, Mary Jo,Ruben, Larry,Pollastri, Michael P.
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p. 777 - 784
(2013/05/09)
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- Optimizing small molecule inhibitors of calcium-dependent protein kinase 1 to prevent infection by toxoplasma gondii
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Toxoplasma gondii is sensitive to bulky pyrazolo [3,4-d] pyrimidine (PP) inhibitors due to the presence of a Gly gatekeeper in the essential calcium dependent protein kinase 1 (CDPK1). Here we synthesized a number of new derivatives of 3-methyl-benzyl-PP (3-MB-PP, or 1). The potency of PP analogues in inhibiting CDPK1 enzyme activity in vitro (low nM IC50 values) and blocking parasite growth in host cell monolayers in vivo (low μM EC 50 values) were highly correlated and occurred in a CDPK1-specific manner. Chemical modification of the PP scaffold to increase half-life in the presence of microsomes in vitro led to identification of compounds with enhanced stability while retaining activity. Several of these more potent compounds were able to prevent lethal infection with T. gondii in the mouse model. Collectively, the strategies outlined here provide a route for development of more effective compounds for treatment of toxoplasmosis and perhaps related parasitic diseases.
- Lourido, Sebastian,Zhang, Chao,Lopez, Michael S.,Tang, Keliang,Barks, Jennifer,Wang, Qiuling,Wildman, Scott A.,Shokat, Kevan M.,Sibley, L. David
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p. 3068 - 3077
(2013/06/05)
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