- Neutralization-Reionization Study of C6H6O Isomers
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Neutralization-reionization (+NR+) mass spectrometry is employed to examine the behavior of C6H6) isomers in the gas phase.Phenol and cyclohexa-2,4-dienone are found not to interconvert following neutralization with mercury of their corresponding cation radicals at 9.9 keV kinetic energy.A very low extent of isomerization is observed following collisional activation of fast C6H6O neutrals with helium.The +NR+ and colisionally activated dissociation spectra, the latter obtained at unit mass resolution, are used to identify these +. isomers.Hexa-1,3,5-trienal is found to cyclize spontaneously to cyclohexa-2,4-dienone during attempted pyrolytic preparation.The thermochemistry of these C6H6O molecules and cation radicals is discussed on the basis of experimental data and MNDO calculations.
- Turecek, Frantisek,Drinkwater, Donald E.,Maquestiau, Andre,McLafferty, Fred W.
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- Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties
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A series of ferrocenyl ketones were synthesized in reaction with ferrocene and corresponding substituted acryloyl chlorides, following previously described procedure. Synthesized products have conjugated enone system, which is suitable for further transformations. In a reaction with hydrazine in acidic medium (acetic acid) new pyrazoline derivatives were obtained. Their antimicrobial properties have been tested. Synthesized pyrazoline derivatives demonstrated expressed in vitro antimicrobial activity towards 12 strains of microorganisms inhibiting all tested bacteria and fungi. The most potent compound in all cases was sorbyl derivative; for bacteria activity was very close to streptomycin, and for fungi in one case the same as ketoconazole. It is established that this compound can be a new, potential antimicrobial agent with minimum inhibitory concentrations from 0.039 to 0.312 mg/mL. One of the starting compounds and two products were crystal substances, suitable for the single crystal X-ray diffraction analysis, which confirmed undoubtedly their structures.
- Burmud?ija, Adrijana,Mu?kinja, Jovana,Ratkovi?, Zoran,Kosani?, Marijana,Rankovi?, Branislav,Novakovi?, Sladjana B.,Bogdanovi?, Goran A.
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- Photoinitiated Polymerization of Columnar Stacks of Self-Assembled Trialkyl-1,3,5-benzenetricarboxamide Derivatives
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A disk-shaped molecule, N-(5-sorbyl-pentyl)-N′,N″ -di(n-octyl)benzene-1,3,5-tricarboxamide (1), has been synthesized and assembled into a columnar stack in cyclohexane. Using a photoinitiated process, we polymerized monomer 1 in its self-assembled state a
- Masuda, Mitsutoshi,Jonkheijm, Pascal,Sijbesma, Rint P.,Meijer
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- Short total synthesis of (-)-kainic acid
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A short total synthesis of (-)-kainic acid has been developed involving a novel diastereofacial differentiating Cu-catalyzed Michael addition-cyclization reaction, which provided access to a chiral pyrroline in a highly stereoselective manner. The chiral pyrroline was converted to (-)-kainic acid via the stereoselective 1,4-reduction of the pyrroline double bond in three steps.
- Oe, Kentaro,Ohfune, Yasufumi,Shinada, Tetsuro
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- Chemo-enzymatic Total Synthesis of Oxosorbicillinol, Sorrentanone, Rezishanones B and C, Sorbicatechol A, Bisvertinolone, and (+)-Epoxysorbicillinol
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The sorbicillinoids are a large family of fungal natural products, many of which possess highly challenging molecular architectures. Depending on their individual structures they exhibit strong biological activities ranging from radical scavenging and anti-infective properties to cytotoxicity. Despite the resulting strong biomedical potential of these natural products and the interest of synthetic chemists owing to their fascinating structures, many sorbicillinoids are currently not synthetically accessible, thus hampering in-depth biological characterization and structural diversification. By using recombinant oxidoreductase SorbC and readily accessible sorbicillin-type synthetic precursors, we have developed enantioselective, one-pot chemo-enzymatic routes to a broad range of sorbicillinoids, thereby establishing total syntheses of oxosorbicillinol, sorrentanone, rezishanones B and C, sorbicatechol A, bisvertinolone, and (+)-epoxysorbicillinol.
- Sib, Anna,Gulder, Tobias A. M.
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- Assembly of fluorinated chromanones: Via enantioselective tandem reaction
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The enantioselective synthesis of fluorinated tricyclic chromanones with multiple vicinal stereogenic centers has been realized for the first time, through the tandem reaction between 2-fluorinated 1-(2-hydroxyaryl)-1,3-diketones and α,β-unsaturated aldehydes. In the presence of chiral amine, the organo-tandem reaction including catalytic Michael addition/cycloketalization/hemiacetalization and acylation sequence provided a wide range of fluorinated tricyclic chromanones with excellent outcomes (>30 examples, up to >99% ee and >19?:?1 d.r.). A plausible catalytic cycle and transition state are also provided for this tandem reaction to rationalize the observed sense of asymmetric induction. This journal is
- Lu, Mengxue,Xiong, Zongli,Zhou, Yuqiao,Wang, Xin,Li, Xiaoyi,Duan, Jingxiang,Yao, Weijun,Xia, Yi,Wang, Zhen
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- A convenient trans diastereoselective synthesis of 3-butadienylazetidinones and their Diels-Alder cycloaddition reactions
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An efficient trans diastereoselective synthesis for azetidinones 3 having 3-dienyl functionalities was developed. The method first involved the [2 + 2] cycloaddition of butadienylketene with various imines 1. The 3-dienyl functionality of the resulting azetidinones 3 was then exploited in Diels-Alder cycloaddition reactions with dienophiles, viz. dimethyl acetylenedicarboxylate (DMAD), maleic anhydride (MA), N-phenylmaleimide (NPM), and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD). The reactions of 3 with DMAD and PTAD resulted in the diastereoselective synthesis of the corresponding Diels-Alder adducts 5a,b and 6. However, the reactions with MA and NPM yielded a mixture (2:1) of diastereoisomers 7/7' and 8/8'.
- Sharma, Arun K.,Mazumdar, Sujit N.,Mahajan, Mohinder P.
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- Synthesis, characterization, and intramolecular Diels-Alder reaction tandem dehydroaromatization of a diene-diyne
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5-(2-Methylthio-4-methyl-5-pyrimidinyl)-2,4-pentadiynyl sorbate 2 was synthesized and characterized. It had two conjugating systems, which made its 5J and 6J 1H-13C correlating signals be obtained in gHMBC spectra. Intramolecular Diels-Alder reaction tandem dehydroaromatization of diene-diyne 2 under heating and irradiating resulted in formation of benzolactone. The reaction underwent the two steps: thermochemistry and photochemistry. The intermediate was confirmed using C60 as an intermediate catcher. This reaction represents a rare example of intramolecular Diels-Alder reaction tandem dehydroaromatization of diene-diyne under mild conditions without catalyst and oxidant. Copyright
- Liu, Shu-Zhi,Tang, Guang-Shi,Wang, Jing,Li, Xue-Hua
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- Effect of Hydroxyl Groups Esterification with Fatty Acids on the Cytotoxicity and Antioxidant Activity of Flavones
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Flavonoids and polyunsaturated fatty acids due to low cytotoxicity in vitro studies are suggested as potential substances in the prevention of diseases associated with oxidative stress. We examined novel 6-hydroxy-flavanone and 7-hydroxy-flavone conjugates with selected fatty acids (FA) of different length and saturation and examined their cytotoxic and antioxidant potential. Our findings indicate that the conjugation with FA affects the biological activity of both the original flavonoids. The conjugation of 6-hydroxy-flavanone increased its cytotoxicity towards prostate cancer PC3 cells. The most noticeable effect was found for oleate conjugate. A similar trend was observed for 7-hydroxy-flavone conjugates with the most evident effect for oleate and stearate. The cytotoxic potential of all tested conjugates was not specific towards PC3 because the viability of human keratinocytes HaCaT cells decreased after exposure to all conjugates. Additionally, we showed that esterification of the two flavonoids decreased their antioxidant activity compared to that of the original compounds. Of all the tested compounds, only 6-sorbic flavanone showed a slight increase in antioxidant potential compared to that of the original compound. Our data show that conjugated flavonoids are better absorbed and enhance cytotoxic effects, but the presence of FA lowered the antioxidant potential.
- Grosicka-Maci?g, Emilia,Kubiak-Tomaszewska, Gra?yna,Roszkowski, Piotr,Struga, Marta,Strzyga-?ach, Paulina
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- Enantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid-Catalyzed Cycloaddition
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A diastereodivergent and enantioselective synthesis of chiral spirocyclohexyl-indolenines with four contiguous stereogenic centers is achieved by a chiral phosphoric acid-catalyzed cycloaddition of 2-susbtituted 3-indolylmethanols with 1,3-dienecarbamates. Modular access to two different diastereoisomers with high enantioselectivities was obtained by careful choice of reaction conditions. Their functional group manipulation provides an efficient access to enantioenriched spirocyclohexyl-indolines and -oxindoles. The origins of this stereocontrol have been identified using DFT calculations, which reveal an unexpected mechanism compared to our previous work dealing with enecarbamates.
- Varlet, Thomas,Mati?i?, Mateja,Van Elslande, Elsa,Neuville, Luc,Gandon, Vincent,Masson, Géraldine
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p. 11611 - 11619
(2021/08/16)
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- Quorum sensing and nf-κb inhibition of synthetic coumaperine derivatives from piper nigrum
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Bacterial communication, termed Quorum Sensing (QS), is a promising target for virulence attenuation and the treatment of bacterial infections. Infections cause inflammation, a process regulated by a number of cellular factors, including the transcription Nuclear Factor kappa B (NF-κB); this factor is found to be upregulated in many inflammatory diseases, including those induced by bacterial infection. In this study, we tested 32 synthetic derivatives of coumaperine (CP), a known natural compound found in pepper (Piper nigrum), for Quorum Sensing Inhibition (QSI) and NF-κB inhibitory activities. Of the compounds tested, seven were found to have high QSI activity, three inhibited bacterial growth and five inhibited NF-κB. In addition, some of the CP compounds were active in more than one test. For example, compounds CP-286, CP-215 and CP-158 were not cytotoxic, inhibited NF-κB activation and QS but did not show antibacterial activity. CP-154 inhibited QS, decreased NF-κB activation and inhibited bacterial growth. Our results indicate that these synthetic molecules may provide a basis for further development of novel therapeutic agents against bacterial infections.
- Baruch, Yifat,Gopas, Jacob,Kadosh, Yael,Kumar, Rajendran Saravana,Kushmaro, Ariel,Muthuraman, Subramani,Yaniv, Karin
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supporting information
(2021/05/28)
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- Palladium-catalysed regio- And stereoselective arylative substitution of γ,δ-epoxy-α,β-unsaturated esters and amides by sodium tetraaryl borates
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Palladium-catalysed reactions of γ,δ-epoxy-α,β-unsaturated esters and amides with NaBAr4 reagents proceeded regio- and stereoselectively, producing allylic homoallyl alcohols with aryl-substituents in the allylic position for a wide range of substrates. A
- Artok, Levent,Bilgi, Yasemin,Ku?, Melih
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supporting information
p. 6378 - 6383
(2020/09/07)
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- Design, synthesis and identification of novel coumaperine derivatives for inhibition of human 5-LOX: Antioxidant, pseudoperoxidase and docking studies
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5-Lipoxygenase (5-LOX) is a key enzyme involved in the biosynthesis of pro-inflammatory leukotrienes, leading to asthma. Developing potent 5-LOX inhibitors especially, natural product based ones, are highly attractive. Coumaperine, a natural product found in white pepper and its derivatives were herein developed as 5-LOX inhibitors. We have synthesized twenty four derivatives, characterized and evaluated their 5-LOX inhibition potential. Coumaperine derivatives substituted with multiple hydroxy and multiple methoxy groups exhibited best 5-LOX inhibition. CP-209, a catechol type dihydroxyl derivative and CP-262-F2, a vicinal trihydroxyl derivative exhibited, 82.7% and 82.5% inhibition of 5-LOX respectively at 20 μM. Their IC50 values are 2.1 ± 0.2 μM and 2.3 ± 0.2 μM respectively, and are comparable to zileuton, IC50 = 1.4 ± 0.2 μM. CP-155, a methylenedioxy derivative (a natural product) and CP-194, a 2,4,6-trimethoxy derivative showed 76.0% and 77.1% inhibition of 5-LOX respectively at 20 μM. Antioxidant study revealed that CP-209 and 262-F2 (at 20 μM) scavenged DPPH radical by 76.8% and 71.3% respectively. On the other hand, CP-155 and 194 showed very poor DPPH radical scavenging activity. Pseudo peroxidase assay confirmed that the mode of action of CP-209 and 262-F2 were by redox process, similar to zileuton, affecting the oxidation state of the metal ion in the enzyme. On the contrary, CP-155 and 194 probably act through some other mechanism which does not involve the disruption of the oxidation state of the metal in the enzyme. Molecular docking of CP-155 and 194 to the active site of 5-LOX and binding energy calculation suggested that they are non-competitive inhibitors. The In-Silico ADME/TOX analysis shows the active compounds (CP-155, 194, 209 and 262-F2) are with good drug likeliness and reduced toxicity compared to existing drug. These studies indicate that there is a great potential for coumaperine derivatives to be developed as anti-inflammatory drug.
- Muthuraman, Subramani,Sinha, Shweta,Vasavi,Waidha, Kamran Manzoor,Basu, Biswarup,Munussami, Punnagai,Balamurali,Doble, Mukesh,Saravana Kumar, Rajendran
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supporting information
p. 604 - 619
(2019/01/14)
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- Synthesis and characterization of unsaturated diacyl and alkyl-acyl piperazine derivatives
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The aim of this study is to obtain new unsaturated piperazine compounds by the reactions of piperazine (1a) and piperazine derivatives (1b–1d) with acylation reactive groups (2a–2j). Methacryloyl piperazine (1b) was synthesized from the reaction of methacrylic anhydride with piperazine (1a). Acyl chlorides (2b–2d) were prepared from the reaction of thionyl chloride with carboxylic acids (3a–3c) obtained as a result of the reaction with malonic acid and suitable aldehyde (5-methylfuran-2-carbaldehyde for 3a, cinnamaldehyde for 3b, and thiophene-2-carbaldehyde for 3c), respectively, by literature methods. Acyl chlorides 2e and 2f were obtained from the reaction of commercially purchased carboxylic acids 3d and 3e with thionyl chloride. Acyl chlorides (2g–2j) were synthesized from the reaction of thionyl chloride with carboxylic acids (3d–3g) transformed from hydrolyzation of esters (4a–4d) obtained as a result of the reaction of triethyl phosphonoacetate with a suitable ketone (acetophenone for 4a, benzophenone for 4b, 1-(5-methylfuran-2-yl)ethan-1-one for 4c, and 1-(thiophen-2-yl)ethan-1-one for 4d), respectively, by literature methods. Unsaturated piperazine derivatives 5a and 5b were obtained from the reaction of 1b with 2b and 2e, respectively. In addition, from the reaction of 1b and acyl chlorides (2b–2j), unsaturated piperazines (5c–5k) were synthesized in medium to good yields (63%–84%). Also, 5l–5g and 5r–5w were obtained from the reaction of allyl piperazine (2c) and cinnamyl piperazine (2d) with acyl chlorides (2a–2f).
- Sari, Sait,ünalan, Seda,Yilmaz, Mehmet
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p. 1656 - 1671
(2020/01/03)
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- Structure–activity relationship investigation of tertiary amine derivatives of cinnamic acid as acetylcholinesterase and butyrylcholinesterase inhibitors: compared with that of phenylpropionic acid, sorbic acid and hexanoic acid
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In the present investigation, 48 new tertiary amine derivatives of cinnamic acid, phenylpropionic acid, sorbic acid and hexanoic acid (4d–6g, 10d–12g, 16d–18g and 22d–24g) were designed, synthesized and evaluated for the effect on AChE and BChE in vitro. The results revealed that the alteration of aminoalkyl types and substituted positions markedly influences the effects in inhibiting AChE. Almost of all cinnamic acid derivatives had the most potent inhibitory activity than that of other acid derivatives with the same aminoalkyl side chain. Unsaturated bond and benzene ring in cinnamic acid scaffold seems important for the inhibitory activity against AChE. Among them, compound 6g revealed the most potent AChE inhibitory activity (IC50 value: 3.64 μmol/L) and highest selectivity over BChE (ratio: 28.6). Enzyme kinetic study showed that it present a mixed-type inhibition against AChE. The molecular docking study suggested that it can bind with the catalytic site and peripheral site of AChE.
- Gao, Xiaohui,Tang, Jingjing,Liu, Haoran,Liu, Linbo,Kang, Lu,Chen, Wen
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p. 519 - 524
(2018/02/27)
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- Synthesis and antimicrobial activities of novel sorbic and benzoic acid amide derivatives
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A series of sorbic and benzoic acid amide derivatives were synthesized by conjugating sorbic acid (SAAD, a1–a7) or benzoic acid (BAAD b1–b6) with amino acid esters and their antimicrobial activities were investigated against Escherichia coli, Bacillus subtilis and Staphylococcus aureus, mixed bacteria from rancid milk, Saccharomyces cerevisiae, and Aspergillus niger. The antimicrobial activity of sorbic acid amides was better than that of benzoic acid amides. The minimum inhibitory concentrations (MIC) of compound isopropyl N-[1-oxo-2, 4-hexadien-1-yl]-L-phenylalaninate (a7) were 0.17 mM against B. subtilis, and 0.50 mM against S. aureus, while the MIC values of sorbic acid were more than 2 mM respectively. Also, compound a7 displayed pH-independent antimicrobial activity in the range of pH 5.0–9.0 and was effective at pH 9.0. These results demonstrated that the conjugation of sorbic acid with amino acid esters led to significant improvement of in vitro antimicrobial attributes, but little effect was observed for benzoic acid amide derivatives.
- Wei, Qingyi,Wang, Xiaomei,Cheng, Jun-Hu,Zeng, Guangxiang,Sun, Da-Wen
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p. 220 - 232
(2018/06/26)
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- Stereoselective Total Synthesis of Bisorbicillinoid Natural Products by Enzymatic Oxidative Dearomatization/Dimerization
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Natural products are a virtually inexhaustible source of small molecules with spectacular molecular architectures and biomedical potential. Their structural complexity generates formidable challenges to total synthesis but often also precludes time- and resource-efficient, stereoselective synthetic access. Biosynthetically, nature frequently uses dimerization and oligomerization reactions to produce highly challenging frameworks from simple starting materials. Impressive examples are the bisorbicillinoids, a family of fungal natural products thought to originate from the polyketide precursor sorbicillin. Utilizing the recombinant oxidoreductase SorbC from the sorbicillin biosynthetic gene cluster, a robust, fully stereoselective synthesis of bisorbicillinoid natural products and unnatural side-chain analogues was developed.
- Sib, Anna,Gulder, Tobias A. M.
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supporting information
p. 12888 - 12891
(2017/09/14)
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- Synthesis of coumaperine derivatives: Their NF-κB inhibitory effect, inhibition of cell migration and their cytotoxic activity
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Coumaperine (an amide alkaloid, present in white piper) and its derivatives were synthesized and investigated for their cytotoxicity against L428 and A549 cells and their NF-κB inhibitory activity. It was found that the coumaperine derivatives CP-9 and CP-38 suppress NF-κB subunits p50 and p65 in nuclear fractions by western blot and by NF-κB luciferase reporter gene assay in a dose dependent manner. Confirmation of these results was obtained by confocal microscopy. CP-9, CP-32 and CP-38 also exhibited dose dependent cell cytotoxicity in a L428?cells expressing constitutively active NF-κB and in A549?cells, with an IC50 value of 43.25?μg/ml, 0.39?μg/ml and 16.85?μg/ml respectively against L428?cells and 57.15?μg/ml, 69.1?μg/ml and 63.2?μg/ml respectively against A549?cells. In addition, the coumaperine derivatives show remarkable inhibitory activity on the cancer cell migration assay against A549 lung adenocarcinoma cells at the concentrations of 5?μg/ml, 10?μg/ml, and 5?μg/ml of CP-9, CP-32 and CP-38 respectively. Aromatic substituents and number of olefinic double bond in coumaperine derivatives found to influence the inhibitory activity. In luciferase reporter gene assay, di-olefin conjugated coumaperine derivatives, CP-38, CP-32 and PIP exhibited higher inhibitory activity than their corresponding tri-olefin conjugated coumaperine derivatives, CP-102, CP-146 and PIP-155 respectively. CP-32 with a stronger electron donating group (-N(CH3)2) showed better inhibitory activity in luciferase reporter gene assay and in cell proliferation of L428?cells. Simple coumaperine derivative (CP-9, with no substituent) effectively inhibited A549?cells proliferation and migration than the other coumaperine derivatives. CP-9 and CP-38 diminish significantly the NF-κB subunits (p50 and p65) of L428?cells in nuclear fractions at the dosage of 10?μg/ml and 30?μg/ml respectively. Which clearly shows that CP-9 and CP-38 inactivate the NF-κB pathway in?vitro.
- Nandakumar, Natarajan,Muthuraman, Subramani,Gopinath, Pushparathinam,Nithya, Pattusamy,Gopas, Jacob,Kumar, Rajendran Saravana
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supporting information
p. 1076 - 1087
(2016/11/09)
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- Copper-Promoted Thiolation of C(sp2)–H Bonds Using a 2-Amino Alkylbenzimidazole Directing Group
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A copper-promoted thiolation of C(sp2)–H bonds with disulfides was achieved by using 2-amino alkylbenzimidazole (MBIP amine) as a new and removable N,N-bidentate directing group. This strategy gives a variety of functionalized thioethers in moderate to excellent yields in a simple and efficient way. Importantly, the substrate scope is not limited to aromatic amides; diverse alkenyl amides are also compatible. Furthermore, this synthetic approach provides a potentially feasible way to achieve structural modification of related benzimidazole-containing compounds through direct C–H activation.
- Liu, Shuang-Liang,Li, Xue-Hong,Shi, Tan-Hao,Yang, Guang-Chao,Wang, Hai-Li,Gong, Jun-Fang,Song, Mao-Ping
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supporting information
p. 2280 - 2289
(2017/05/01)
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- Coumarin esterified derivative with effect of inhibiting transcriptional activity of RXRalpha (Retinoid X Receptor) as well as preparation method and application of coumarin esterified derivative
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The invention discloses a coumarin esterified derivative with an effect of inhibiting transcriptional activity of RXRalpha (Retinoid X Receptor) as well as a preparation method and application of the coumarin esterified derivative. The coumarin esterified derivative is a 4-chloromethyl-7-hydroxy coumarin esterified derivative shown by the following general formula. The invention also discloses a preparation method of the 4-chloromethyl-7-hydroxy coumarin esterified derivatives. The preparation method comprises the following steps: preparing 4-chloromethyl-7-hydroxy coumarin under solvent-free conditions by taking anhydrous bismuth chloride as a catalyst; preparing corresponding acyl chloride through different side chain acids; and reacting with the 4-chloromethyl-7-hydroxy coumarin, thereby obtaining the corresponding compound. The coumarin esterified derivative disclosed by the invention has a certain effect of inhibiting the transcriptional activity of RXRalpha and provides a thought for developing medicines taking the RXRalpha as a target. The structural formula is as shown in the specification.
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Paragraph 0036
(2017/09/26)
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- 2-pyrindine ethyl ester compound and application
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The invention discloses a 2-pyrindine ethyl ester compound with the structural formula as indicated in the formula (I) and salt thereof, wherein R is H3C-CH2-CH2-CH2-CH2-or H3C-CH=CH-CH=CH-; inorganic acid salt of the compound in the formula (I) refers to hydrochloride or phosphate or nitrate, and organic acid salt refers to citrate or lactate or oxalate or sulfanilate. The compound in the formula (I) and the salt thereof have excellent plant growth regulation activity, can be used individually or combined with other active components and is used for increasing the yield and improving the quality of crops.
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Paragraph 0021; 0022; 0023; 0025
(2016/11/17)
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- Antibacterial preservative is sorbic acid amino ester derivative and its preparation method
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The invention belongs to the field of synthesis of a drug, and relates to a sorbic acid-amino acid ester derivate of an antimicrobial preservative and a preparation method thereof. The preparation method comprises the steps of: enabling amino acid and alcohol to react to generate amino-acid ester by utilizing an acyl chloride method, and then reacting with amino-acid ester by sorbic acid after acylating chlorination, so as to synthesize the amino acid ester derivate of the sorbic acid. The amino acid ester derivate of the novel compound sorbic acid obtained by the method has no sensitization on skin of a human body, is suitable for different pH systems with large ranges, has antibacterial broad-spectrum property and good potential application value, and can be used as the antimicrobial preservative applied to corrosion prevention and antibiosis of foods, drugs, cosmetics, pesticides, leather products and wood materials.
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Paragraph 0038
(2016/11/02)
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- Synthesis of polymeric ladders by topochemical polymerization
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Two polymeric ladders were synthesized by topochemical polymerization. The critical assemblies with multiple reactive centers were characterized by single crystal X-ray diffraction. Approximately 64% and 70% of the mass of the two polymeric ladders can be
- Hou, Xiaodong,Wang, Zhihan,Lee, Joseph,Wysocki, Erin,Oian, Casey,Schlak, Jennifer,Chu, Qianli R.
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supporting information
p. 1218 - 1220
(2014/02/14)
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- Preparation of conjugated 1,3-enynes by Rh(III)-catalysed alkynylation of alkenes via C-H activation
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An experimentally simple additive-free Rh(III)-catalysed direct alkynylation of alkenes has been developed. This protocol employs commercially available TIPS-EBX as the alkyne source, giving access to conjugated terminal enynes following a simple silyl-de
- Collins, Karl D.,Lied, Fabian,Glorius, Frank
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supporting information
p. 4459 - 4461
(2014/04/17)
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- Synthetic studies towards radicicol through biomimetic macrolactonization and transannular aromatization reactions
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Studies towards the total synthesis of the natural product radicicol are described that employ a late-stage esterification and aromatization by trapping a ketene intermediate. The subsequent biomimetic aromatization of the resultant triketo ester gave hig
- Cookson, Rosa,Poeverlein, Christoph,Lachs, Jennifer,Barrett, Anthony G. M.
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p. 4523 - 4535
(2014/08/05)
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- Iron-Catalyzed Regio- And Stereoselective Substitution of γ,δ-Epoxy-α,β-unsaturated Esters and Amides with Grignard Reagents
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Chemical Equetion Presentation When γ,δ-epoxy-α,β- unsaturated esters or amides were treated with 2 equiv of Grignard reagents in the presence of 10-24 mol % FeCl2, regio- and stereoselective substitution of the epoxide moiety with the Grignard reagent occurred to give exclusively δ-hydroxy-γ-alkyl or aryl-α,β-unsaturated esters or amides in good yields.
- Hata, Takeshi,Bannai, Rie,Otsuki, Mamoru,Urabe, Hirokazu
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supporting information; scheme or table
p. 1012 - 1014
(2010/06/15)
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- Degradable polymer and process for production thereof
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In one embodiment of the present invention, a degradable polymer having a peroxide bond therein is disclosed. The degradable polymer can be utilized in the fields of medicals or medical materials, can be applied to a DDS or gene delivery system, and can be used as a novel polymeric material or environmentally-friendly material. A polyperoxide, which is an alternating copolymer, has in a side chain thereof, a functional group (which is a substituent comprising a therapeutic molecule), a water-soluble substituent, or a biodegradable substituent.
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Page/Page column 7; 9
(2009/04/24)
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- Highly regio- and stereoselective addition of organolithium reagents to extended conjugate amides using (S,S)-(+)-pseudoephedrine as chiral auxiliary
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(Chemical Equation Presented) The conjugate addition of organolithium reagents to polyunsaturated conjugate amides containing (S,S)-(+)- pseudoephedrine as chiral auxiliary has been studied in detail. The reaction proceeded with good 1,4-selectivity and e
- Ocejo, Marta,Carrillo, Luisa,Badia, Dolores,Vicario, Jose L.,Fernandez, Naiara,Reyes, Efraim
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supporting information; experimental part
p. 4404 - 4407
(2009/09/06)
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- Ligand controlled highly regio- and enantioselective synthesis of α-acyloxyketones by palladium-catalyzed allylic alkylation of 1,2-enediol carbonates
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The palladium catalyzed decarboxylative asymmetric allylic alkylation of allyl 1,2-enediol carbonates 1 can decompose to either α-hydroxyketones 3 or α-hydroxyaldehydes 4. The product distribution is largely controlled by the ligand. Using Lnaph/sub
- Trost, Barry M.,Xu, Jiayi,Schmidt, Thomas
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supporting information; experimental part
p. 11852 - 11853
(2009/02/05)
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- Cl3CCONH2/PPh3: A versatile reagent for synthesis of esters
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Cl3CCONH2/PPh3 was a versatile reagent to convert carboxylic acids into their corresponding acid chlorides. This intermediate was clearly confirmed by spectroscopic methods (IR, 1H, 13C NMR). This one-pot reaction of in situ acid chloride generated with various alcohols successfully furnished the corresponding esters in moderate to excellent yields. Copyright ? Taylor & Francis Group, LLC.
- Chantarasriwong, Oraphin,Jang, Doo Ok,Chavasiri, Warinthorn
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experimental part
p. 2845 - 2856
(2009/04/11)
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- Quantitative structure-activity relationship studies for prediction of antimicrobial activity of synthesized 2,4-hexadienoic acid derivatives
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A new series of 2,4-hexadienoic acid derivatives (S1-S42) has been synthesized and evaluated as antimicrobial agents against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Candida albicans, and Aspergillus niger. Quantitative structure-activity relationship (QSAR) investigation using Hansch analysis was applied to find out correlation between antimicrobial activities with physicochemical properties of the synthesized compounds. Various physicochemical descriptors and experimentally determined minimum inhibitory concentration values for different microorganisms were used as independent and dependent variables, respectively. The QSAR revealed that topological parameters especially molecular connectivity indices (χ2, 0χv, 2χv) were found to have overall significant correlation with antimicrobial activity of 2,4-hexadienoic acid derivatives. The statistical results of training set, cross-validated r2 and conventional r values gave reliability to the prediction of molecules with activity using QSAR models.
- Narasimhan, Balasubramanian,Judge, Vikramjeet,Narang, Rakesh,Ohlan, Ruchita,Ohlan, Sucheta
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p. 5836 - 5845
(2008/03/18)
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- Rhodium-catalyzed asymmetric 1,6-addition of aryl zinc reagents to dienones
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(Chemical Equation Presented) A highly enantioselective methodology allows the preparation of α,β-unsaturated ketones that contain a new stereogenic center at the C5 position. This approach is realized through the title reaction in the presence of chlorotrimethylsilane as a Lewis acid and a rhodium/(S)-binap complex as the catalyst followed by acidic hydrolysis (see scheme). binap = 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl.
- Hayashi, Tamio,Yamamoto, Shohei,Tokunaga, Norihito
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p. 4224 - 4227
(2007/10/03)
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- Synthesis of dihydronaphthalenes via aryne Diels-Alder reactions: Scope and diastereoselectivity
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Novel aryne Diels-Alder reactions with functionalized acyclic dienes are reported. These give useful cis-substituted dihydronaphthalene building blocks in good yield which are not easily accessible via other means, as demonstrated in the synthesis of sert
- Dockendorff, Chris,Sahli, Stefan,Olsen, Madeline,Milhau, Ludovic,Lautens, Mark
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p. 15028 - 15029
(2007/10/03)
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- Asymmetric total synthesis of sperabillins B and D via lithium amide conjugate addition
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Diastereoselective conjugate addition of homochiral lithium (R)-N-allyl-N-α-methylbenzylamide to methyl (2E,5E)-hepatadienoate, followed by protecting group manipulation and subsequent iodocyclocarbamation allows a concise route to the core fragment, methyl (3R,5R,6R)-3,6-diamino-5- hydroxyheptanoate, of sperabillins B and D. Differentiation between the C-3 and C-6 primary amino groups of this core amino acid was readily achieved by treatment with acetone, giving the 5,6-isopropylidene and C-3-imine protected diamine, with subsequent regioselective acylation of the C-6-nitrogen facilitating the total synthesis of sperabillin D in 10.8% overall yield, and the first asymmetric synthesis of sperabillin B in 5.8% overall yield.
- Davies, Stephen G.,Haggitt, Jane R.,Ichihara, Osamu,Kelly, Richard J.,Leech, Michael A.,Mortimer, Anne J. Price,Roberts, Paul M.,Smith, Andrew D.
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p. 2630 - 2649
(2007/10/03)
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- Syntheses and QSAR studies of sorbic, cinnamic and ricinoleic acid derivatives as potential antibacterial agents
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Amides and esters of sorbic, cinnamic and ricinoleic acid have been synthesized and evaluated for their antibacterial activity against gram (+) ve S. aureus, B. subtilis and gram (-) ve E. coli. Most of the compounds have shown moderate to good activity against microorganisms under test. Linear regression analysis of descriptors related to lipophilicity, steric and electronic parameters against antibacterial activity have been performed. QSAR studies indicated the predominance of electronic and steric parameters over the lipophilicity parameters in contributing antibacterial activity.
- Narasimhan,Kothawade,Pharande,Mourya,Dhake
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p. 2828 - 2834
(2007/10/03)
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- Synthesis of unsymmetrically substituted 1,3-butadiynes and 1,3,5-hexatriynes via alkylidene carbenoid rearrangements
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Unsymmetrically substituted 1,3-butadiynes and 1,3,5-hexatriynes are synthesized in four steps from commercially available aldehydes or carboxylic acids. The key step in this process involves a Fritsch-Buttenberg-Wiechell rearrangement, in which an alkylidene carbenoid intermediate subsequently rearranges to the desired polyyne. This rearrangement proceeds under mild conditions, and it is tolerant of a range of functionalities. In general, the procedurally facile formation of the dibromoolefinic precursors, in combination with the effectiveness of the rearrangement step, makes this procedure an attractive alternative to traditional methods for di- and triyne synthesis that utilize palladium or copper catalysis.
- Shi Shun, Annabelle L. K.,Chernick, Erin T.,Eisler, Sara,Tykwinski, Rik R.
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p. 1339 - 1347
(2007/10/03)
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- Long-acting, chemical-resistant skin emollients, moisturizers, and strengtheners
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The present invention relates to compounds that are two-part molecules, and compositions containing such compounds, in which one part is designed to become covalently bonded to the skin (bonding agent) and the other part (a characteristic use agent) is designed to impart some characteristic use, such as emolliency, moisturizing effect, anti-acne, anti-wrinkle, anti-pain, antimicrobial, antifungal, antiviral, anti-irritation, skin tanning and skin lightening effects, extended protection of the skin (e.g., from ultraviolet light, by incorporation of a sunscreen component; from toxic and/or irritating substances; from insects and skin parasites, by incorporation of insecticides and/or insect repellants; from free radicals or other agents, as in aging, by incorporation of antioxidants), or dyeing of hair, skin nails, wool or fuir. The covalently bonded part may also be useful to impart skin strengthening effect (e.g., from shear forces) or as wound healing agents.
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- Reaction of N,N-dialkyl-N-(trimethylsilyl)methyl-γ-substituted allylammonium salts with cesium fluoride
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The reaction of N,N-dialkyl-N-(trimethylsilyl)methyl-γ- (methoxycarbonyl or cyano)allylammonium salts (1e, g, h) with cesium fluoride in N,N-dimethylformamide (DMF) did not form the expected allyl rearrangement products 3 of N-methylides 2, and instead gave N,N-dialkyl-3-(methoxycarbonyl or cyano)-2-(fluoromethyl)propylamines (9e, g, h) as the main product. The reaction mechanism is discussed.
- Zhang, Chen,Maeda, Yasuhiro,Sato, Yoshiro
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p. 572 - 576
(2007/10/03)
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- HETERO-DIELS-ALDER REACTIONS OF DIMETHYL 1-OXO-(E,E)-2,4-HEXADIENEPHOSPHONATE WITH 2-ALKYLIDENE-1,3-DITHIANES
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The cycloaddition reactions of dimethyl 1-oxo-(E,E)-2,4-hexadiene phosphonate (1) with 2-alkylidene-1,3-dithianes 4 and 5 gave oxa-dithiaspiro-undecene-2-phosphonate derivatives.The reactions were responsive to electrophilic assistance by the solvent as well as 'conventional' Lewis Acid catalysis.The structural constitutions and preferred conformations of these pyran derivatives were established by NMR spectroscopy as well as by the X-ray crystallographic determination of a key derivative.In addition to E- to Z-double bond isomerization reactions in 1 and acyl chloride 2, α-acyl phosphonate 1 underwent thermal isomerization to dimethyl 2H-pyran-6-phosphonate (6).Key words: Diels-Alder/reactions, phosphonates, NMR Lewis acid catalysis, pyrans.
- Schuster, Thomas,Evans, Slayton A.
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p. 259 - 272
(2007/10/02)
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- Stereoselective reduction of β,δ-diketo esters. A novel strategy for the synthesis of artificial HMG-CoA reductase inhibitors
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Condensation of N-methoxy-N-methyl amides with the dianions of acetoacetates gives in good yields β,δ-diketo esters, which are reduced with Et2BOMe-NaBH4 in tetrahydrofuran-methanol highly selectively to give syn-β,δ-dihydroxy esters in one step. Similarly, the β,δ-diketo esters of the Taber's chiral alcohol or its enantiomer respectively are reduced to give syn-β,δ-dihydroxy esters of moderate enantiomeric excess. Higher diastereo- and enantioselectivity were achieved by reduction of the β,δ-diketo esters of the Taber's chiral alcohol or its enantiomer successively with diisobutylalane and with Et2BOMe-NaBH4. The resulting syn-diol esters were hydrolyzed and lactonized to give various types of β-hydroxy-δ-lactones commonly found in artificial HMG-CoA reductase inhibitors.
- Hiyama,Reddy,Minami,Hanamoto
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p. 350 - 363
(2007/10/02)
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- Stereoselectivity and Generality of the Palladium-Catalysed Cyclopropanation of α,β-Unsaturated Carboxylic Acids Derivatized with Oppolzer's Sultam
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A series of α,β-unsaturated carboxylic acids derivatized with camphorsultam 1 a s a chiral auxiliary has been stereoselectively cyclopropanated. the selectivity of the reaction produces cyclopropanated products with the 1R,2R absolute configuration as indicated by the optical rotations as well as by an X-ray structure determineation.The temperature dependence of the reaction was studied with three substrates. the highest stereoselectivity was obtained at temperatures above 25 deg C.Branching at the α- or β-carbons disfavours complete conversion, and electron-withdrawing substituents at these positions seem to prevent the reaction.The auxiliary was removed by using titanium(IV) isopropoxide in benzyl alcohol followed by alkaline hydrolysis of the intermediate ester. the potent 5-HT1A receptor agonist (1R,2S)-2-(2-hydroxyphenyl)-N,N-dipropylcyclopropylamine 13 was synthesized by this method
- Vallaerda, Jerk,Appelberg, Ulf,Csoeregh, Ingeborg,Hacksell, Uli
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p. 461 - 470
(2007/10/02)
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- Asymmetric Induction at C(β) and C(α) of N-Enoylsultams by Organomagnesium 1,4-Addition/Enolate Trapping
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The 1,4-addition of alkylmagnesium chlorides to conjugated N-enoylsultams and subsequent 'enolate trapping' with aq.NH4Cl or MeI/hexamethylphosphoric triamide generated centers of asymmetry at C(β) and/or at C(α) with good to excellent ?-face differentation as demonstrated by the conversions 1->2, 1->4, and 8->9.This holds also for the regioselective 1,4-addition of EtMgCl to a dienosultam (15->16).Reactive conformations 1, 8, 13, and 14 are postulated in agreement with X-ray evidence which also served for the structure determination of the product 9j.
- Oppolzer, Wolfgang,Poli, Giovanni,Kingma, Arend J.,Starkemann, Christian,Bernardinelli, Gerald
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p. 2201 - 2214
(2007/10/02)
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- SYNTHESE REGIOSPECIFIQUE D'AMIDO-1 VINYL-2 CYCLOPROPANES A PARTIR DE LITHIENS ALLYLIQUES MONOHALOGENES ET D'AMIDES TERTIAIRES α-ETHYLENIQUIES
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Chloroallyllitium and gem-chloro(methyl)allyllithium readly react, via conjugated addition and cyclisation, with α-ethylenic aliphatic tertiary amides to produce, in a "one-pot" reaction, alkyl-substituted 1-amido-2-vinylcyclopropanes.
- Ongoka, Pascal,Mauze, Bernard,Miginiac, Leone
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p. 131 - 140
(2007/10/02)
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- SYNTHESIS AND PROPERTIES OF LIQUID CRYSTALS. III. CHOLESTERYL ESTERS OF SOME CIS,TRANS-ISOMERIC UNSATURATED ACIDS
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A series of esters of cholesterol with the cis,trans isomers of unsaturated monocarboxylic acids were synthesized.The effect of the nature and of the configuration of the substituents in relation to the double bond in the acid component of the cholesterol esters on the mesogenic capacity was established.The phase transition temperatures were determined.
- Bogat-skii, A. V.,Galantina, A. I.,Derkach, L. G.,Taubert D.
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p. 2072 - 2075
(2007/10/02)
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