cas 622-88-8, 4-Bromophenylhydrazine hydrochloride

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Design, Synthesis, and Antifungal Activity of 2,6-Dimethyl-4-aminopyrimidine Hydrazones as PDHc-E1 Inhibitors with a Novel Binding Mode
A series of novel 2,6-dimethyl-4-aminopyrimidine hydrazones 5 were rationally designed and synthesized as pyruvate dehydrogenase complex E1 (PDHc-E1) inhibitors. Compounds 5 strongly inhibited Escherichia coli (E. coli) PDHc-E1 (IC50 values 0.94-15.80 μM). As revealed by molecular docking, site-directed mutagenesis, enzymatic, and inhibition kinetic analyses, compounds 5 competitively inhibited PDHc-E1 and bound in a "straight"pattern at the E. coli PDHc-E1 active site, which is a new binding mode. In in vitro antifungal assays, most compounds 5 at 50 μg/mL showed more than 80% inhibition against the mycelial growth of six tested phytopathogenic fungi, including Botrytis cinerea, Monilia fructigena, Colletotrichum gloeosporioides, andBotryosphaeria dothidea. Notably, 5f and 5i were 1.8-380 fold more potent against M. fructigena than the commercial fungicides captan and chlorothalonil. In vivo, 5f and 5i controlled the growth of M. fructigena comparably to the commercial fungicide tebuconazole. Thus, 5f and 5i have potential commercial value for the control of peach brown rot caused by M. fructigena.
Zhou, Yuan,Zhang, Shasha,Cai, Meng,Wang, Kaixing,Feng, Jiangtao,Xie, Dan,Feng, Lingling,Peng, Hao,He, Hongwu
p. 5804 - 5817
(2021/06/25)

Highly Efficient Synthesis of Hindered 3-Azoindoles via Metal-Free C-H Functionalization of Indoles
Although 3-azoindoles have recently emerged as an appealing family of photoswitch molecules, the synthesis of such compounds has been poorly covered in the literature. Herein a high-yielding and operationally simple protocol is reported allowing the synthesis of 3-azoindoles, featuring important steric hindrance around the azo motif. Remarkably, this C-H coupling is characterized by excellent atom economy and occurs under metal-free conditions, at room temperature, and within few minutes, delivering the expected products in excellent yields (quantitatively in most of the cases). Accordingly, a library of new molecules, with potential applications as photochromic compounds, is prepared.
Guillemard, Lucas,Jacob, Nicolas,Wencel-Delord, Joanna
supporting information
p. 574 - 580
(2020/02/13)

Heterocyclic com pounds and organic light-emitting diode including the same
The present invention relates to a novel heterocyclic compound and an organic electroluminescent device comprising the same. The heterocyclic compound is represented by the following Chemical Formula 1, and the organic electroluminescent device including the heterocyclic compound has excellent driving voltage, luminous efficiency, and lifespan properties. Chemical Formula 1. (by machine translation)
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Paragraph 0657-0663

(2021/01/19)

An electroluminescen compound and an electroluminescent device comprising the same
The present invention relates to an organic light-emitting compound represented by chemical formula 1. An organic electroluminescent device comprising the organic light-emitting compound in the present invention has excellent power efficiency, light-emitting efficiency, and long life cycle because the present invention can be operated by a lower driving-voltage in comparison with a device comprising conventional phosphorescent host materials.
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Paragraph 0390-0394

(2021/02/02)

Synthesis and Characterization of Telmisartan-Derived Cell Death Modulators to Circumvent Imatinib Resistance in Chronic Myeloid Leukemia
New strategies to eradicate cancer stem cells in chronic myeloid leukemia (CML) include a combination of imatinib with peroxisome proliferator-activated receptor gamma (PPARγ) ligands. Recently, we identified the partial PPARγ agonist telmisartan as effective sensitizer of resistant K562 CML cells to imatinib treatment. Here, the importance of the heterocyclic core on the cell death-modulating effects of the telmisartan-derived lead 4′-((2-propyl-1H-benzo[d]imidazol-1-yl)methyl)-[1,1′-biphenyl]-2-carboxylic acid (3 b) was investigated. Inspired by the pharmacodynamics of HYL-6d and the selective PPARγ ligand VSP-51, the benzimidazole was replaced by a carbazole or an indole core. The results indicate no correlation between PPARγ activation and sensitization of resistant CML cells to imatinib. The 2-COOH derivatives of the carbazoles or indoles achieved low activity at PPARγ, while the benzimidazoles showed 60-100 % activation. Among the 2-CO2CH3 derivatives, only the ester of the lead (2 b) slightly activated PPARγ. Sensitizing effects were further observed for this non-cytotoxic 2 b (80 % cell death), and to a lesser extent for the lead 3 b or the 5-Br-substituted ester of the benzimidazoles (5 b).
Schoepf, Anna M.,Salcher, Stefan,Hohn, Verena,Veider, Florina,Obexer, Petra,Gust, Ronald
supporting information
p. 1067 - 1077
(2020/05/25)

Multinuclear 2-(Quinolin-2-yl)quinoxaline-Coordinated Iridium(III) Complexes Tethered by Carbazole Derivatives: Synthesis and Photophysics
Five mono/di/trinuclear iridium(III) complexes (1-5) bearing the carbazole-derivative-tethered 2-(quinolin-2-yl)quinoxaline (quqo) diimine (N^N) ligand were synthesized and characterized. The photophysical properties of these complexes and their corresponding diimine ligands were systematically studied via UV-vis absorption, emission, and transient absorption (TA) spectroscopy and simulated by time-dependent density functional theory. All complexes possessed strong well-resolved absorption bands at 400 nm that have predominant ligand-based 1π,π? transitions and broad structureless charge-transfer (1CT) absorption bands at 400-700 nm. The energies or intensities of these 1CT bands varied pronouncedly when the number of tethered Ir(quqo)(piq)2+ (piq refers to 1-phenylisoquinoline) units, πconjugation of the carbazole derivative linker, or attachment positions on the carbazole linker were altered. All complexes were emissive at room temperature, with 1-3 showing near-IR (NIR) 3MLCT (metal-to-ligand charge-transfer)/3LLCT (ligand-to-ligand charge-transfer) emission at ～710 nm and 4 and 5 exhibiting red or NIR 3ILCT (intraligand charge-transfer)/3LMCT (ligand-to-metal charge-transfer) emission in CH2Cl2. In CH3CN, 1-3 displayed an additional emission band at ca. 590 nm (3ILCT/3LMCT/3MLCT/3π,π? in nature) in addition to the 710 nm band. The different natures of the emitting states of 1-3 versus those of 4 and 5 also gave rise to different spectral features in their triplet TA spectra. It appears that the parentage and characteristics of the lowest triplet excited states in these complexes are mainly impacted by the πsystems of the bridging carbazole derivatives and essentially no interactions among the Ir(quqo)(piq)2+ units. In addition, all of the diimine ligands tethered by the carbazole derivatives displayed a dramatic solvatochromic effect in their emission due to the predominant intramolecular charge-transfer nature of their emitting states. Aggregation-enhanced emission was also observed from the mixed CH2Cl2/ethyl acetate or CH2Cl2/hexane solutions of these ligands.
Zhu, Xiaolin,Liu, Bingqing,Cui, Peng,Kilina, Svetlana,Sun, Wenfang
supporting information
p. 17096 - 17108
(2020/11/30)

Allylic and Allenylic Dearomatization of Indoles Promoted by Graphene Oxide by Covalent Grafting Activation Mode
The site-selective allylative and allenylative dearomatization of indoles with alcohols was performed under carbocatalytic regime in the presence of graphene oxide (GO, 10 wt percent loading) as the promoter. Metal-free conditions, absence of stoichiometric additive, environmentally friendly conditions (H2O/CH3CN, 55 °C, 6 h), broad substrate scope (33 examples, yield up to 92 percent) and excellent site- and stereoselectivity characterize the present methodology. Moreover, a covalent activation model exerted by GO functionalities was corroborated by spectroscopic, experimental and computational evidences. Recovering and regeneration of the GO catalyst through simple acidic treatment was also documented.
Lombardi, Lorenzo,Bellini, Daniele,Bottoni, Andrea,Calvaresi, Matteo,Monari, Magda,Kovtun, Alessandro,Palermo, Vincenzo,Melucci, Manuela,Bandini, Marco
supporting information
p. 10427 - 10432
(2020/07/24)

Boron difluoride formazanates with thiophene and 3,4-ethylenedioxythiophene capping and their electrochemical polymerization
We report here the first example of BF2formazanates with thiophene capping and their π-conjugated polymers in the form of electroactive uniform thin films by electrochemical polymerization. These new formazanates and their polymers possess panc
Agrawal, Abhijeet R.,Banewar, Vishal W.,Das, Sarasija,Ghosh, Nani Gopal,Karmakar, Himadri S.,Kumar, Chandan,Kumar, Neha Rani,Zade, Sanjio S.
supporting information
p. 13202 - 13206
(2020/10/13)

Heterocyclic com pounds and organic light-emitting diode including the same
PURPOSE: A heterocyclic compound and an organic electroluminescent device containing the same are provided to show stability compared with an existing material and to have superior light emitting properties such as low driving voltage or current efficiency. CONSTITUTION: A heterocyclic compound is denoted by chemical formula 1. An organic electroluminescent device comprises an anode, a cathode, and layers containing the heterocyclic compounds, which is placed between the anode and the cathode. A light emitting layer between the anode and the cathode contains the heterocyclic compounds. The organic electroluminescent device further comprises one or more layers selected among a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
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Paragraph 0279; 0286-0291; 0324-0330

(2019/08/30)

Heterocyclic com pounds and organic light-emitting diode including the same
The present invention relates to novel heterocyclic compounds of chemical formula 1 and an organic electroluminescent device containing the same as a light emitting material and, more specifically, to stable heterocyclic compounds with superior light emitting properties such as driving voltage and light emitting efficiency; and an organic electroluminescent device containing the same. Also, the present invention provides an organic electroluminescent device comprising an anode, a cathode, and layers which are inserted between the anode and the cathode and contain the heterocyclic compounds of chemical formula 1.
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Paragraph 0186; 0187-0192

(2019/11/29)

Aromatic compound and organoelectroluminescent device comprising the compound
The present invention relates to a novel aromatic compound and an organic electroluminescent device comprising the same. The present invention relates to an organic electroluminescent device including an aromatic compound. (by machine translation)
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Paragraph 0057; 0076-0081

(2019/12/10)

Heterocyclic com pounds and organic light-emitting diode including the same
PURPOSE: A heterocyclic compound and an organic electroluminescent device containing the same are provided to show stability and superior light emitting properties such as low driving voltage or current efficiency. CONSTITUTION: A heterocyclic compound is denoted by chemical formula 1. An organic electroluminescent device comprises an anode, a cathode, and layers containing the heterocyclic compounds, which are placed between the anode and the cathode. A light emitting layer between the anode and the cathode contains the heterocyclic compounds. The organic electroluminescent device comprises a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
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Paragraph 0263-0269

(2019/06/04)

Design, synthesis and biological evaluation of novel indole derivatives as potential HDAC/BRD4 dual inhibitors and anti-leukemia agents
HDAC inhibitors and BRD4 inhibitors were considered to be potent anti-cancer agents. Recent studies have demonstrated that HDAC and BRD4 participate in the regulation of some signal paths like PI3K-AKT. In this work, a series of indole derivatives that co
Cheng, Gaoliang,Wang, Zhi,Yang, Jinyu,Bao, Yu,Xu, Qihao,Zhao, Linxiang,Liu, Dan
p. 410 - 417
(2019/01/03)

Design, synthesis and biological evaluation of tryptamine salicylic acid derivatives as potential antitumor agents
A series of tryptamine salicylic acid derivatives were synthesized and their antiproliferative activity against MGC-803, MCF-7, HepG2, A549 and HeLa cell lines was evaluated. The structure-activity relationship (SAR) study revealed that different substitutions of the C5 and C3′-C5′ positions have certain effects on the anti-proliferation activity. The growth assay revealed that N-[2-(5-bromo-1H-indol-3-yl)-ethyl]-2-hydroxy-3-methyl-benzamide (E20) showed the most potent and broad-spectrum anticancer inhibition of all the cell lines evaluated, and was only more potent than 5-Fu for the gastric cancer cell line. Preliminary studies indicated that compound E20 could inhibit colony formation and migration of MGC-803 cells. The flow cytometry (FCM) results showed that compound E20 arrested the cell cycle in the G2/M phase and induced apoptosis of MGC-803 cells in a concentration-dependent manner. In addition, the western blot results showed that E20 can down-regulate the expression of hexokinase 2. Our studies suggest that the framework of N-[2-(5-bromo-1H-indol-3-yl)-ethyl]-2-hydroxy-3-methyl-benzamide may be consider as a new type of chemical for designing effective anti-cancer drugs targeting gastric cancer cells.
Xiong, Runde,He, Dongxiu,Deng, Xiangping,Liu, Juan,Lei, Xiaoyong,Xie, Zhizhong,Cao, Xuan,Chen, Yanming,Peng, Junmei,Tang, Guotao
p. 573 - 583
(2019/04/30)

Synthesis and evaluation of indole derivatives as photosynthesis and plant growth inhibitors
Indole derivatives were synthetized based on the Fischer indole methodology using different phenyl hydrazine hydrochlorides and either cyclohexanone or 2-butanone. The pre- and post-emergent herbicidal activities were evaluated against Ipomoea grandifolia. A carbazole, 6-chloro-2,3,4,9-tetrahydro-1H-carbazole (3b), decreased the PIabs parameter by 32% and increased the cross-section related parameters, indicating the inactivation of the reaction center on photosystem II. Compound 3b acts as a post-emergent herbicide prototype since dry biomass was reduced by 50%, corroborating the fluorescence results. Comparing instead with a germination experiment, 2,3,4,9-tetrahydro-1H-carbazole (3a) was found to be the most effective agent, inhibiting seed germination by 22% and decreasing root length by 50%. The tetrahydrocarbazoles showed better results than indole derivatives potentially due to the presence of methylene groups at structures, which increase the compounds' lipophilicity and may facilitate their access to the plant. In addition, electron withdrawing groups on the aromatic ring were found to correlate with increased herbicide activity. Further optimization of this series towards the development of herbicides is ongoing.
Mendes, Mylla Cristie Da Silva,Fazolo, Bruno Rodrigues,De Souza, Jéssica Maria,De Vasconcelos, Leonardo Gomes,De Sousa Junior, Paulo Teixeira,Dall'Oglio, Evandro Luiz,Soares, Marcos Ant?nio,Sampaio, Olívia Moreira,Vieira, Lucas Campos Curcino
p. 1350 - 1358
(2019/06/19)

Discovery of 1,3,4-oxadiazol-2-one-containing benzamide derivatives targeting FtsZ as highly potent agents of killing a variety of MDR bacteria strains
The spread of infections caused by multidrug-resistant (MDR) pathogens, such as methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant S. aureus (VRSA), has created a need for new antibiotics with novel mechanisms of action. The bacterial division protein FtsZ has been identified as a novel drug target that can be exploited clinically. As part of an ongoing effort to develop FtsZ-targeting antibacterial agents, we describe herein the design, synthesis and bioactivity of six series of novel 1,3,4-oxadiazol-2-one-containing, 1,2,4-triazol-3-one-containing and pyrazolin-5-one-containing benzamide derivatives. Among them, compound A14 was found to be the most potent antibacterial agent, much better than clinical drugs such as ciprofloxacin, linezolid and erythromycin against all the tested gram-positive strains, particularly methicillin-resistant, penicillin-resistant and clinical isolated S. aureus. Subsequent studies on biological activities and docking analyses proved that A14 functioned as an effective compound targeting FtsZ. Preliminary SAR indicated a general direction for further optimization of these novel analogues. Taken together, this research provides a promising chemotype for developing newer FtsZ-targeting bactericidal agents.
Bi, Fangchao,Song, Di,Qin, Yinhui,Liu, Xingbang,Teng, Yuetai,Zhang, Na,Zhang, Panpan,Zhang, Nan,Ma, Shutao
p. 3179 - 3193
(2019/06/17)

Synthesis of Aryl Hydrazines via CuI/BMPO Catalyzed Cross-Coupling of Aryl Halides with Hydrazine Hydrate in Water
The N,N’-bis(2,6-dimethylphenyl)oxalamide was discovered as a powerful ligand for Cu-catalyzed cross-coupling of aryl halides with hydrazine hydrate, leading to the formation of a variety of aryl hydrazines at 80 oC in water under the assistance of K3PO4 and 4 mol% cetyltrimethylammonium bromide from aryl bromides and aryl iodides. Good to excellent yields were observed in most cases.
Kumar, Siripuram Vijay,Ma, Dawei
supporting information
p. 1003 - 1006
(2018/09/20)

Indole hydroxamic acid compounds with anti-tumor activity and application of compounds
The invention belongs to the technical field of medicines and relates to indole hydroxamic acid compounds with anti-tumor activity, in particular to hydroxamic acid compounds containing 1,3,5-trisubstituted indole, pharmaceutically accepted salt and hydra
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Paragraph 0045-0048

(2019/01/16)

Synthesis, in vitro Antimicrobial, and Cytotoxic Activities of New 1,3,4-Oxadiazin-5(6H)-one Derivatives from Dehydroabietic Acid
A series of new 1,3,4-oxadiazin-5(6H)-one derivatives (6a–n) of dehydroabietic acid were designed and synthesized as potential antimicrobial and antitumor agents. Their structures were characterized by IR, 1H NMR, 13C NMR, MS, and elemental analyses. All the title compounds were evaluated for their antimicrobial activity against four bacterial and three fungal strains using the serial dilution method. Among them, compound 6e showed the highest antibacterial activity against Bacillus subtilis with a minimum inhibitory concentration (MIC) value of 1.9 μg/mL. In addition, the in vitro cytotoxic activities of the title compounds were also assayed against three human carcinoma cell lines (MCF-7, SMMC-7721, and HeLa) through the MTT colorimetric method. As a result, compounds 6b, 6g, 6k, and 6m exhibited significant inhibition against at least one cell line with IC50 values below 10 μM. Compound 6m was especially found to be the most potent derivative with IC50 values of 2.26 ± 0.23, 0.97 ± 0.11, and 1.89 ± 0.31 μM against MCF-7, SMMC-7721, and HeLa cells, respectively, comparable to positive control etoposide.
Jin, Xiao-Yan,Zhang, Kang-Ping,Chen, Hao,Miao, Ting-Ting,Wang, Shi-Fa,Gu, Wen
p. 538 - 547
(2018/06/11)

A class of 1, 5 - diphenyl pyrazole - 3 - carboxylic acid compound and use thereof
The invention provides a 1, 5-diphenyl pyrazol-3-carboxylic acid compound and application thereof. The compound has a structure as shown in general formula I, wherein R1 is selected from -H, halogen, saturated alkyl of C1-C6, or -X1-R4; R2 is selected from H, halogen, saturated alkyl of C1-C6, or -X2-R5; R3 is selected from H, -NH2 or -NH-CO-Ph-(o, m, p)R6; R6 is selected from H, halogen, saturated alkyl of C1-C6, or -O-R7; X1 and X2 are respectively selected from O or S independently; R4, R5 and R7 are respectively selected from H, saturated alkyl of C1-C6, benzyl or phenyl substituted by saturated alkyl of C1-C6 independently. The compound provided by the invention simulates BH3-only and p53TAD protein alpha-helix at the same time, competitively binds and antagonize Mcl-1, Bcl-2 and MDM2 protein, and specifically causes tumor cell apoptosis, thereby realizing application as an anticancer compound. (general formula I).
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Paragraph 0117; 0119

(2017/10/31)

Rh(II)-catalyzed intramolecular annulation of N-sulfonyl 1,2,3-triazoles with indole derivatives: A new method for synthesis pyranoindoles
A direct and highly stereoselective approach for the synthesis of Z-alkenyl-pyranoindoles had been developed by utilizing Rh(II)-catalyzed intramolecular cyclization of N-sulfonyl-1,2,3-triazoles with indole derivatives. A variety of pyranoindoles were obtained in 44-93% yields. Moreover, a more convenient synthesis of pyranoindoles starting from terminal alkyne was realized via a Cu-Rh sequentially catalyzed one-pot cascade reaction.
Xie, Hui,Yang, Jian-Xin,Bora, Pranjal Protim,Kang, Qiang
supporting information
p. 3014 - 3021
(2016/05/19)

A diversity-oriented approach to indolocarbazoles: Via Fischer indolization and olefin metathesis: Total synthesis of tjipanazole D and i
New synthetic strategies to indolocarbazoles have been reported via two-fold Fischer indolization under green conditions using l-(+)-tartaric acid and N,N-dimethyl urea. Starting with cyclohexanone, a bench-top starting material, this methodology has been extended to the total synthesis of natural products such as tjipanazoles D and I as well as the core structure of asteropusazole and racemosin B. Here, atom economical reactions like ring-closing metathesis, enyne-metathesis, and the Diels-Alder reaction have been used as key steps. Diverse strategies demonstrated here are useful in medicinal chemistry and materials science to design a library of decorated indoles.
Kotha, Sambasivarao,Saifuddin, Mohammad,Aswar, Vikas R.
supporting information
p. 9868 - 9873
(2016/10/31)

Rhodium(III)-catalyzed in situ oxidizing directing group- assisted c-h bond activation and olefination: A route to 2-vinylanilines
A new and efficient method for the synthesis of 2-vinylanilines from the reaction of arylhydrazine hydrochlorides with alkenes and diethyl ketone via a rhodium-catalyzed C-H activation is described. The oxidant-free olefination reaction involves the in situ generation of an -N-N=CR1R2 moiety as the oxidizing directing group thus providing an easy access to 2-vinylanilines.
Muralirajan, Krishnamoorthy,Haridharan, Radhakrishnan,Prakash, Sekar,Cheng, Chien-Hong
supporting information
p. 761 - 766
(2015/03/18)

Synthesis, fungicidal activity, structure-activity relationship and density functional theory studies of novel oxime ether derivatives containing 1-aryl-3-oxypyrazoles
A series of 16 oxime ether derivatives containing 1-aryl-3-oxypyrazoles were synthesised, and the structure of one of them, (E)-methyl 2-(2-({(1-(4-chlorophenyl)-1H-pyrazol-3-yl)-oxy}methyl)phenyl)-2-(methoxyimino)acetate was determined by X-ray diffraction crystallography. Preliminary bioassays indicated that some of these compounds exhibited very good fungicidal activities against Rhizoctonia solani, especially the ester 2-(2-({(1-(4-chlorophenyl)-1H-pyrazol-3-yl)-oxy}methyl)phenyl)-2-(methoxyimino)acetate, which displayed greater activity than control compound pyraclostrobin at a dosage of 0.1 μg mL-1. The relationship between structure and fungicidal activity was discussed. Density functional theory studies of the 3-methyl heterocyclic ester and the 4-chorophenyl heterocyclic N-methylamide were carried out and the results discussed in terms of the wide difference in fungicidal activity shown by each compound.
Lv, Kunzhi,Liu, Yuanyuan,Li, Yi,Xu, Guanghui,Pan, Xuechun,Li, Fangshi,Chen, Kai,Huang, Bin,Yang, Yaping
p. 594 - 600
(2015/11/27)

Design, synthesis, crystal structures, and insecticidal activities of eight-membered azabridge neonicotinoid analogues
Three series of novel azabridge neonicotinoid analogues were designed and synthesized, which were constructed by starting material A, glutaraldehyde, and primary amine hydrochlorides (aliphatic amines, phenylhydrazines, and anilines). Most of the eight-membered azabridge compounds presented higher insecticidal activities than oxabridged compound B against cowpea aphid (Aphis craccivora) and brown planthopper (Nilaparvata lugens). Compared with imidacloprid, some azabridged compounds exhibited excellent insecticidal activity against brown planthopper. The crystal structures and bioassay indicated that changing bridge atoms from O to N could lead to entirely different conformations, which might be the important influential factor of the bioactivities.
Xu, Renbo,Xia, Rui,Luo, Ming,Xu, Xiaoyong,Cheng, Jiagao,Shao, Xusheng,Li, Zhong
p. 381 - 390
(2014/02/14)

Regioselective synthesis of indoles via rhodium-catalyzed C-H activation directed by an in-situ generated redox-neutral group
A regioselective synthesis of indoles from arylhydrazine hydrochlorides with alkynes and diethyl ketone catalyzed by a rhodium complex is described. A possible mechanism involving an in-situ generated oxidizing directing group -N-Ni'CR1R2 assisted ortho-C-H activation and reductive elimination are proposed. The catalytic reaction is highly compatible with a wide range of functional arylhydrazines and alkynes. The reaction proceeds under mild reaction conditions and is atom-step economical.
Muralirajan, Krishnamoorthy,Cheng, Chien-Hong
p. 1571 - 1576
(2014/06/09)

Targeting low-druggability bromodomains: Fragment based screening and inhibitor design against the BAZ2B bromodomain
Bromodomains are epigenetic reader domains that have recently become popular targets. In contrast to BET bromodomains, which have proven druggable, bromodomains from other regions of the phylogenetic tree have shallower pockets. We describe successful tar
Ferguson, Fleur M.,Fedorov, Oleg,Chaikuad, Apirat,Philpott, Martin,Muniz, Joao R. C.,Felletar, Ildiko,Von Delft, Frank,Heightman, Tom,Knapp, Stefan,Abell, Chris,Ciulli, Alessio
supporting information
p. 10183 - 10187
(2014/01/17)

Indole synthesis by rhodium(III)-catalyzed hydrazine-directed C-H activation: Redox-neutral and traceless by N-N bond cleavage
Fishing for complements! There is an alternative to the useful Fischer indole synthesis. The new method utilizes the same retrosynthetic disconnection but is based on a RhIII-catalyzed directed C-H activation step and a successive coupling with alkynes. Copyright
Zhao, Dongbing,Shi, Zhuangzhi,Glorius, Frank
supporting information
p. 12426 - 12429
(2013/12/04)

Piecing together the puzzle: Understanding a mild, metal free reduction method for the large scale synthesis of hydrazines
A key intermediate for the synthesis of hydrazines via a mild, metal free reduction of diazonium salts has been isolated and characterized by X-ray analysis. The presence of this intermediate is general, as demonstrated by the preparation of a number of analogues. A discussion of the mechanism and potential benefits of such a process are also described.
Browne, Duncan L.,Baxendale, Ian R.,Ley, Steven V.
supporting information; experimental part
p. 10296 - 10303
(2012/01/04)

Design and synthesis of antifungal benzoheterocyclic derivatives by scaffold hopping
The incidence of invasive fungal infections and associated mortality is increasing dramatically. Although azoles are first-line antifungal agents, cross-resistance and hepatic toxicity are their two major limitations. The discovery of novel non-azole lead compounds will be helpful to overcome these problems. On the basis of our previously reported benzopyran non-azole CYP51 inhibitor, scaffold hopping was used to design structurally diverse new compounds and expand the structure-activity relationships of the lead structure. Five kinds of scaffolds, namely benzimidazole, benzoxazole, benzothiazole, quinazolin-4-one and carboline, were chosen for synthesis. In vitro antifungal activity data and results from molecular docking revealed that the scaffold was important for the antifungal activity. Several compounds showed potent activity against both standard and clinically resistant fungal pathogens, suggesting that they can serve as a good starting point for the discovery of novel antifungal agents.
Sheng, Chunquan,Che, Xiaoying,Wang, Wenya,Wang, Shengzheng,Cao, Yongbing,Yao, Jianzhong,Miao, Zhenyuan,Zhang, Wannian
scheme or table
p. 1706 - 1712
(2011/05/06)

ENANTIOSELECTIVE PROCESS FOR THE PREPARATION OF ZOLMITRIPTAN
An enantioselective process for preparing zolmitriptan, (S)-4-{[3-[2-(dimethylamine)ethyl]-1H-indol-5-yl]methyl}-2-oxazolidinone), by asymmetric hydrogenation of (Z)-2-(acetylamino)-3-{[3-N,N-(dimethylamine)ethyl)-1H-indol-5-yl]-2-propenoic acid methyl ester in the presence of hydrogen and an enantioselective chiral phosphine transition metal catalyst.
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(2010/09/05)

Synthesis and antimicrobial activities of novel 1H-dibenzo[a,c]carbazoles from dehydroabietic acid
A series of novel 1H-dibenzo[a,c]carbazole derivatives were synthesized in good yield through reaction of methyl 7-oxo-dehydroabietate with a variety of substituted phenylhydrazines. The structures of the newly synthesized compounds were confirmed by IR, 1H NMR, MS spectral studies and elemental analysis. All compounds were investigated for their activity against four bacteria (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas fluorescens) and three fungi (Trichophyton rubrum, Candida albicans and Aspergillus niger). Among the compound tested, 6d, 6e, 6f and 6m exhibited pronounced antibacterial activities and 6e and 6m also showed moderate antifungal activities. Particularly, 6d exhibited stronger antibacterial activity against B. subtilis comparable to positive control.
Gu, Wen,Wang, Shifa
experimental part
p. 4692 - 4696
(2010/10/03)

Synthesis, crystal structure and fungicidal activities of new type oxazolidinone-based strobilurin analogues
A series of oxazolidinone-based strobilurin analogues were efficiently synthesized by the reaction of 3-(2-bromomethylphenyl) oxazolidin-2-one with 1-substituted phenyl-2H-pyrazolin-3-one. Their structures were confirmed and characterized by 1H-NMR, 13C-NMR, elemental analysis, and mass spectroscopy. In addition, the crystal structure of the target compound 3-(2-((1-phenyl-2H-pyrazol-3-yloxy)methyl)phenyl) oxazolidin-2-one was determined by single crystal X-ray diffraction. The bioassay results of these compounds indicated that some of the oxazolidin-2-one derivatives containing N-substituted phenyl 2H-pyrazol ring exhibited potential in vivo fungicidal activities against M. grisea at the dosage of 1 g L-1.
Li, Yuhao,Liu, Rui,Yan, Zhangwei,Zhang, Xiangning,Zhu, Hongjun
experimental part
p. 3341 - 3347
(2012/05/05)

Synthesis and structure of indoline spiropyrans of the coumarin series
New indoline spiropyrans of the coumarin series were synthesized by the condensation of indoline and hydroxyformylcoumarin derivatives. Spiropyrans, viz., derivatives of 8-formyl-7-hydroxy-4-methylcoumarin and 5-formyl-6-hydroxy-4-methylcoumarin, under irradiation are transformed into open forms, which are recyclized in the dark. The compounds formed by the condensation of the indoline derivatives with 3-formyl-4-hydroxycoumarin have an open structure of the merocyanine dyes and are transformed into spiro forms neither in the dark nor under irradiation with the visible light.
Traven,Miroshnikov,Chibisova,Barachevsky,Venidiktova,Strokach
p. 2417 - 2424
(2007/10/03)

INDOLIN PHENYLSULFONAMIDE DERIVATIVES
The invention relates to novel substituted indolin phenylsulfonamide derivatives, to a method for the production thereof and to the use thereof in medicaments, especially as potent PPAR-delta activating compounds for the prophylaxis and/or treatment of cardiovascular diseases, especially dyslipidaemia and coronary heart diseases.
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Page/Page column 56; 57

(2010/11/30)