cas 1199-77-5, alpha-Methylcinnamic acid | Articles data

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Water-initiated hydrocarboxylation of terminal alkynes with CO2and hydrosilane
This work discloses a Cu(ii)-Ni(ii) catalyzed tandem hydrocarboxylation of alkynes with polysilylformate formed from CO2and polymethylhydrosiloxane that affords α,β-unsaturated carboxylic acids with up to 93% yield. Mechanistic studies indicate that polysilylformate functions as a source of CO and polysilanol. Besides, a catalytic amount of water is found to be critical to the reaction, which hydrolyzes polysilylformate to formic acid that induces the formation of Ni-H active species, thereby initiating the catalytic cycle.
Wang, Meng-Meng,Lu, Sheng-Mei,Paridala, Kumaraswamy,Li, Can
supporting information
p. 1230 - 1233
(2021/02/09)

Discovery of a novel inhibitor of nitric oxide production with potential therapeutic effect on acute inflammation
Inflammation as a host's excessive immune response to stimulation, is involved in the development of numerous diseases. To discover novel anti-inflammatory agents and based on our previous synthetic work on marine natural product Chrysamide B, it and a series of derivatives were synthesized and evaluated for their anti-inflammatory activity on inhibition of LPS-induced NO production. Then the preliminary structure–activity relationships were conducted. Among them, Chrysamide B is the most potent anti-inflammatory agent with low cytotoxicity and strong inhibition on the production of NO (IC50 = 0.010 μM) and the activity of iNOS (IC50 = 0.082 μM) in LPS-stimulated RAW 264.7 cells. Primary studies suggested that the mechanism of action may be that it interfered the formation of active dimeric iNOS but not affected transcription and translation. Furthermore, its good performance of anti-inflammatory effect on LPS-induced multiple inflammatory cytokines production, carrageenan-induced paw edema, and endotoxin-induced septic mice, was observed. We believe that these findings would provide an idea for the further modification and research of these analogs in the future.
Zhu, Long-Qing,Fan, Xiao-Hong,Li, Jun-Fang,Chen, Jin-Hong,Liang, Yan,Hu, Xiao-Ling,Ma, Shu-Meng,Hao, Xiang-Yong,Shi, Tao,Wang, Zhen
supporting information

(2021/05/26)

Chrysamide B derivative with anti-tumor activity and preparation and application of Chrysamide B derivative
The invention belongs to the field of medicinal chemistry, and particularly relates to a marine natural product Chrysamide B and a derivative thereof. The marine natural product Chrysamide B comprisesstereoisomers or pharmaceutically acceptable salts, solvates and prodrugs of the marine natural product Chrysamide B, general formulas are shown in a formula (I), a formula (II) and a formula (III).The invention also provides preparation and application of the compound. The compound has an anti-cancer effect; the compound has good inhibitory activity on digestive system cancers, leukemia, livertumors, non-small cell lung cancers, cervical cancers, breast cancers and the like and has the effects of inducing tumor cell apoptosis, activating apoptosis protein expression, retarding cycle, inhibiting proliferation and the like and is a potential antitumor drug.
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Paragraph 0053-0055; 0057

(2020/08/02)

Electrocatalytic asymmetric hydrogenation of α,β-unsaturated acids in a PEM reactor with cinchona-modified palladium catalysts
We have developed an electrocatalytic asymmetric hydrogenation reaction using a proton-exchange membrane (PEM) reactor that employs a polymer electrolyte fuel cell and industrial electrolysis technologies. Reasonable enantioselectivities and excellent current efficiencies were obtained in the asymmetric hydrogenation of α-phenylcinnamic acid under mild conditions without adding a supporting electrolyte. The current density was crucial to achieving the improved results observed.
Atobe, Mahito,Fukazawa, Atsushi,Hashimoto, Yasushi,Sato, Yasushi,Tanaka, Kenta
(2020/04/28)

Design, synthesis and biological evaluation of tetrazole-containing RXRα ligands as anticancer agents
Nuclear receptor RXRα plays an important role in many biological and pathological processes. The nongenomic action of RXRα is implicated in many cancers. K-8008, a non-canonical RXRα ligand derived from sulindac, inhibits the TNFα-activated PI3K/AKT pathway by mediating the interaction between a truncated form of RXRα (tRXRα) and the p85α regulatory subunit of PI3K and exerts potent anticancer activity in animal model. Herein we report our studies of a novel series of K-8008 analogs as potential anticancer agents targeting RXRα. Two compounds 8b and 18a were identified to have slightly stronger binding to RXRα and improved apoptotic activities in breast cancer cells.
Yan, Zhiqiang,Chong, Shuyi,Lin, Huiyun,Yang, Qian,Wang, Xin,Zhang, Weidong,Zhang, Xiaokun,Zeng, Zhiping,Su, Ying
p. 562 - 575
(2019/01/10)

Bioreduction of α-Acetoxymethyl Enones: Proposal for an SN2′ Mechanism Catalyzed by Enereductase
(Z)-3-Acetoxymethyl-4-R-3-buten-2-ones (R=aryl, alkyl) and (Z)-3-methyl-4-R-3-buten-2-ones (R=aryl) were synthesized and submitted to reduction by the yeast Saccharomyces cerevisiae producing the (R)- and (S)-4-R-3-methybutan-2-ones, respectively. This stereochemistry control strategy was applied in the syntheses of (R)- and (S)-Tropional with moderate to high enantiomeric excesses. Other (Z)-3-acyloxymethyl-4-phenyl-3-buten-2-ones showed similar behavior to the (Z)-3-acetoxymethyl counterpart, and the acylated Morita–Baylis–Hillman adduct 1-acetoxy-2-methylene-1-phenylbutan-3-one produced a mixture of products, with and without the acetoxy group, via three different reaction pathways. In addition to experiments employing whole cells, those in which isolated enereductases were used suggested that the main pathway through which the loss of the acetoxy group occurs during the biocatalytic cascade is an SN2′-type reaction, rather than formal hydrogen addition followed by acetic acid elimination. Finally, related ethyl enones were reduced enantioselectively by the yeast Candida albicans, producing both (R)- and (S)-reduction products, depending on the presence of the acetoxy group in the starting material. (Figure presented.).
Paula, Bruno R. S.,Zampieri, Davila,Rodrigues, J. Augusto R.,Moran, Paulo J. S.
p. 3555 - 3571
(2016/11/25)

The Development of a Stereoselective Method for the Synthesis of Tetrasubstituted Derivatives of α,β-Unsaturated Carboxylic Acids
Alkenes possessing four different carbon-linked substituents are the main structural motif of many biologically active compounds. The derivatives of (2E)-3-(3-methoxyphenyl)-2-methylpent-2-enoic acid ((E)-2c) are suitable precursors for the synthesis of Tapentadol, a novel centrally acting analgesic. It was found that the Ni-carbometallation reaction of disubstituted alkyne 8 with CO2and an Et2Zn allows for efficient and practical preparation of (E)-2c as a single (E)-regioisomer in 89% of isolated yield. The influence of the size of the aliphatic substituent of alkyne and the steric hindrance of the organozinc reagent on stereochemical course of the carbometallation reaction was evaluated. Finally, air-stable Ni(dme)Cl2was proposed as an alternative to widely used Ni(cod)2catalyst.
Rzymkowski, Jan,Pi?tek, Anna
p. 665 - 673
(2016/09/21)

Palladium-Catalyzed Hydrocarboxylation of Alkynes with Formic Acid
A palladium-catalyzed hydrocarboxylation of alkynes with formic acid has been developed. The method provides acrylic acid and derivatives in good yields with high regioselectivity without the need to handle toxic CO gas. Nontoxic: Acrylic acids are an important chemical feedstock. The title reaction provides acrylic acid and derivatives in good yields with high regioselectivities without the need to handle toxic CO gas.
Hou, Jing,Xie, Jian-Hua,Zhou, Qi-Lin
supporting information
p. 6302 - 6305
(2015/05/20)

Systematic methodology for the development of biocatalytic hydrogen-borrowing cascades: Application to the synthesis of chiral α-substituted carboxylic acids from α-substituted α,β-unsaturated aldehydes
Ene-reductases (ERs) are flavin dependent enzymes that catalyze the asymmetric reduction of activated carbon-carbon double bonds. In particular, α,β-unsaturated carbonyl compounds (e.g. enals and enones) as well as nitroalkenes are rapidly reduced. Conversely, α,β-unsaturated esters are poorly accepted substrates whereas free carboxylic acids are not converted at all. The only exceptions are α,β-unsaturated diacids, diesters as well as esters bearing an electron-withdrawing group in α- or β-position. Here, we present an alternative approach that has a general applicability for directly obtaining diverse chiral α-substituted carboxylic acids. This approach combines two enzyme classes, namely ERs and aldehyde dehydrogenases (Ald-DHs), in a concurrent reductive-oxidative biocatalytic cascade. This strategy has several advantages as the starting material is an α-substituted α,β-unsaturated aldehyde, a class of compounds extremely reactive for the reduction of the alkene moiety. Furthermore no external hydride source from a sacrificial substrate (e.g. glucose, formate) is required since the hydride for the first reductive step is liberated in the second oxidative step. Such a process is defined as a hydrogen-borrowing cascade. This methodology has wide applicability as it was successfully applied to the synthesis of chiral substituted hydrocinnamic acids, aliphatic acids, heterocycles and even acetylated amino acids with elevated yield, chemo- and stereo-selectivity. A systematic methodology for optimizing the hydrogen-borrowing two-enzyme synthesis of α-chiral substituted carboxylic acids was developed. This systematic methodology has general applicability for the development of diverse hydrogen-borrowing processes that possess the highest atom efficiency and the lowest environmental impact. This journal is
Knaus, Tanja,Mutti, Francesco G.,Humphreys, Luke D.,Turner, Nicholas J.,Scrutton, Nigel S.
supporting information
p. 223 - 233
(2015/02/19)

Chiral Cyclopentadienyl Iridium(III) Complexes Promote Enantioselective Cycloisomerizations Giving Fused Cyclopropanes
The cyclopentadienyl (Cp) group is a very important ligand for many transition-metal complexes which have been applied in catalysis. The availability of chiral cyclopentadienyl ligands (Cpx) lags behind other ligand classes, thus hampering the investigation of enantioselective processes. We report a library of chiral CpxIrIII complexes equipped with an atropchiral Cp scaffold. A robust complexation procedure reliably provides CpxIrIII complexes with tunable counterions. In a proof-of-concept application, the iodide-bearing members are shown to be highly selective for enyne cycloisomerization reactions. The dehydropiperidine-fused cyclopropane products are formed in good yields and enantioselectivities.
Dieckmann, Michael,Jang, Yun-Suk,Cramer, Nicolai
supporting information
p. 12149 - 12152
(2015/10/12)

Investigation of sol-gel supported palladium catalysts for Heck coupling reactions in o/w-microemulsions
Sol-gel supported palladium catalysts are investigated for the Heck coupling reaction between styrene and iodo-/bromobenzene to trans-stilbenes in o/w-microemulsions as alternative reaction medium. High conversions and selectivities are obtained with these catalysts and they show better catalytic performance than their commercial analogs Pd@SiO2 or Pd/C. The influence of the catalyst structure on the activity is investigated in detail showing mass transport limitations that can be optimized by the palladium loading. The catalyst is recyclable >6 times with negligible palladium leaching into the solution. Because of the good recyclability under retention of activity and selectivity, the influence of transport limitations is suppressed and the total catalyst efficiency is increased to more than 2.
Volovych,Kasaka,Schwarze,Nairoukh,Blum,Fanun,Avnir,Schom?cker
p. 210 - 221
(2014/07/22)

Superacid BF3-H2O promoted benzylation of arenes with benzyl alcohols and acetates initiated by trace water
A convenient procedure employing simple starting materials benzyl alcohols and acetates as the benzyl donors to assemble a series of diarylalkanes through benzylation of arenes using in situ prepared superacid BF3-H 2O as an efficient promoter has been developed. The beneficial role of water in the reaction has been clarified with combination of control experiments and 11B NMR analysis. This reaction is a self-promoted model, which is triggered by the trace of water and continuously promoted by self released by-product water (or carboxylic acid). A wide range of substrates are investigated and the moderate to excellent yields and the good regioselectivities for secondary benzyl alcohols as well as arenes bearing electron-withdrawing groups have been achieved. As a result, moisture in the reaction system has been utilized as an efficient initiator in all benzylation cases.
Zhang, Shuting,Zhang, Xiaohui,Ling, Xuege,He, Chao,Huang, Ruofeng,Pan, Jing,Li, Jiaqiang,Xiong, Yan
p. 30768 - 30774
(2014/08/05)

Synthesis and SAR study of modulators inhibiting tRXRα-dependent AKT activation
RXRα represents an intriguing and unique target for pharmacologic interventions. We recently showed that Sulindac and a designed analog could bind to RXRα and modulate its biological activity, including inhibition of the interaction of an N-terminally truncated RXRα (tRXRα) with the p85α regulatory subunit of phosphatidylinositol-3-OH kinase (PI3K). Here we report the synthesis, testing and SAR of a series of novel analogs of Sulindac as potential modulators for inhibiting tRXRα-dependent AKT activation. A new compound 30 was identified to have improved biological activity.
Wang, Zhi-Gang,Chen, Liqun,Chen, Jiebo,Zheng, Jian-Feng,Gao, Weiwei,Zeng, Zhiping,Zhou, Hu,Zhang, Xiao-Kun,Huang, Pei-Qiang,Su, Ying
p. 632 - 648
(2013/05/09)

Lyaseenzymes, Nucleic Acids Encoding Them and Methods For Making and Using Them
This invention provides polypeptides having lyase activity, polynucleotides encoding these polypeptides, and meth-°ds of making and using these polynucleotides and polypeptides. In one aspect, the invention is directed to polypeptides having ammonia lyase activity, e.g., phenylalanine ammonia lyase, tyrosine ammonia lyase and/or histidine ammonia lyase activity, including thermostable and thermotolerant activity, and polynucleotides encoding these enzymes, and making and using these polynucleotides and polypeptides. The polypeptides of the invention can be used in a variety of pharmaceutical, agricultural and industrial contexts. X═NO2, Cl, Br, NH2, OH, H, alkyl at one or several o, m, and p positions R═H or alkyl.
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(2012/07/27)

Domino carbopalladation-cross-coupling for the synthesis of 3,3-disubstituted oxindoles
This study examines a domino carbopalladation-cross-coupling reaction for the formation of valuable oxindole scaffolds. Furthermore, the reaction sequence forges vicinal stereocenters in a stereospecific manner through the formation of two carbon-carbon bonds and, thereby, rapidly generates complexity. The reaction gives high yields for a variety of acrylamide substrates, and various organoboranes have also been evaluated for the cross-coupling. This work offers insight into the relative rates determining a successful carbopalladation-cross- coupling reaction and how to favor the desired reaction pathway.
Seashore-Ludlow, Brinton,Somfai, Peter
supporting information; experimental part
p. 3858 - 3861
(2012/09/11)

Lyase Enzymes, Nucleic Acids Encoding Them and Methods for Making and Using Them
This invention provides polypeptides having lyase activity, polynucleotides encoding these polypeptides, and methods of making and using these polynucleotides and polypeptides. In one aspect, the invention is directed to polypeptides having ammonia lyase activity, e.g., phenylalanine ammonia lyase, tyrosine ammonia lyase and/or histidine ammonia lyase activity, including thermostable and thermotolerant activity, and polynucleotides encoding these enzymes, and making and using these polynucleotides and polypeptides. The polypeptides of the invention can be used in a variety of pharmaceutical, agricultural and industrial contexts.
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(2011/02/25)

Polyvinylpyrrolidone-supported hydroperoxide for selective oxidation of aldehydes to carboxylic acids and sulfides to sulfoxides
The facile immobilization of hydroperoxide on the cross-linked poly(vinylpyrrolidone) is described by treatment of a poly(vinylpyrrolidone)- Vilsmeier adduct with (35%) hydrogen peroxide. The in situ-generated poly(vinyl pyrrolidone)-supported hydroperoxide reagent showed very good performance in chemoselective oxidation of aldehydes to carboxylic acids as well as sulfides to sulfoxides. Supplemental materials are available for this article. Go to the publishers online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Taylor & Francis Group, LLC.
Lakouraj, Moslem Mansour,Aghajani, Bahareh,Mokhtary, Masoud
experimental part
p. 2393 - 2401
(2011/03/17)

Hydrocarboxylation of allenes with CO2 catalyzed by silyl pincer-type palladium complex
Tridentate PSiP pincer-type palladium complex-catalyzed hydrocarboxylation of allenes under carbon dioxide to give synthetically useful β,γ-unsaturated carboxylic acids was developed. This novel CO2-fixation reaction is thought to proceed through the catalytic generation of σ-allyl palladium species via hydropalladation of allenes, followed by its regioselective nucleophilic addition to CO2 in the presence of an appropriate reducing agent. The reaction is successfully applied to various allenes bearing functional groups such as ester, carbamate, ketone, and alkene, showing high synthetic utility of this protocol. Copyright
Takaya, Jun,Iwasawa, Nobuharu
supporting information; experimental part
p. 15254 - 15255
(2009/03/12)

Stereoselective hydroxycarbonylation of vinyl bromides to α,β-unsaturated carboxylic acids in the ionic liquid [BMIM]PF 6
(E/Z)-Isomers containing vinyl bromides were stereoselectively carbonylated to the corresponding (E)-α,β-ethylenic carboxylic acids in the ionic liquid [BMIM]PF6. Vinyl dibromides also underwent hydroxycarbonylation to give monoacids. The products are pure by proton NMR spectroscopic determination without purification by silica gel column chromatograghy or recrystallization.
Zhao, Xiaodan,Alper, Howard,Yu, Zhengkun
p. 3988 - 3990
(2007/10/03)

A facile synthesis of 2-benzyloxy/2-(4-isopropylbenzyloxy)-2-methyl-3-(4- substituted phenyl)propanoic acid based insulin sensitizing agents: RSR 13-15 and PKR13-15
The title compounds (RSR13-15) and (PKR13-15) were prepared by the etherification of benzyl alcohol and 4-isopropylbenzyl alcohol respectively with ethyl-2-bromo-2-methyl-3-(4-substituted phenyl)propanoates in the presence of sodium hydride in THF followed by alkaline hydrolysis of the ethyl esters. The substituted propanoic acids used in this synthetic sequence were prepared by magnesium-methanol reduction of correspondingly substituted propenoic acids, which in turn were prepared via 'Perkin Reaction' of 4-substituted benzaldehydes with propanoic anhydride. The details of the synthetic sequence followed for the preparation of all these compounds having almost all the structural features required for a compound to act as a potent insulin sensitizing agent are reported. Birkhaeuser Boston 2004.
Verma, Raman K.,Singla, Rubina,Punniyakoti
p. 660 - 676
(2007/10/03)

4-endo-trig cyclization processes using bis(collidine)bromine(i) hexafluorophosphate as reagent: Preparation of 2-oxetanones, 2-azetidinones, and oxetanes
Reaction in methylene chloride of bis(collidine)bromine(I) hexafluorophosphate with α,β-unsaturated acids and α,β-unsaturated N- sulfonamides was found to lead diastereospecifically to the corresponding 2- oxetanones and 2-azetidinones in moderate yields (23-60%), by an almost unknown 4-endo cyclization. This process allow the synthesis of these interesting classes of products in one step from common substrates. Similarly, the reaction of cinnamic alcohols led, by the same cyclization procedure, to oxetanes (20-36%); the presence of a gem-dimethyl group in α of the alcohol function appeared beneficial.
Homsi, Fadi,Rousseau, Gerard
p. 81 - 85
(2007/10/03)

A Catalytic Synthesis of Nitriles from Aldehydes and Alcohols in the Presence of Aqueous Ammonia by Oxidation with N2SO4-K2S2O8
Aromatic and conjugated aldehydes were converted to nitriles by nickel-catalyzed oxidation in the presence of aqueous ammonia with K2S2O8 under the basic aqueous conditions. this reaction could be applied to alcohols as the starting materials.
Yamazaki, Shigakazu,Yamazaki, Yasuyuki
p. 571 - 574
(2007/10/02)

IODOARYLATION OF ACRYLONITRILE AND ACRYLIC ESTERS WITH ARENEDIAZONIUM SALTS
In the reaction of acrylic esters and acrylonitrile with arenediazonium salts in the presence of alkali-metal iodides the products from addition of the aryl radical and iodine at the double bond are formed.An effective method is proposed for the synthesis of 1-iodo-1-methoxycarbonyl(cyano)-2-arylalkanes, which enter readily into nucleophilic substitution of iodine.When boiled with an alcohol solution of alkali, they are transformed into derivatives of cinnamic acid.
Ganushchak, N. I.,Obushak, N. D.,Polishchuk, O. P.
p. 2291 - 2295
(2007/10/02)

IODOARYLATION OF UNSATURATED COMPOUNDS
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Ganushchak, N. I.,Obushak, N. D.,Polishchuk, O. P.
p. 595 - 596
(2007/10/02)

IDENTIFICATION OF LOW-BOILING FRACTION OF PYROLYSIS OIL
Composition of the low-boiling fraction of the pyrolysis oil obtained from continuous rectification has been determined by combination of capillary gas-liquid chromatography with other identification methods (catalytic hydrogenation, polymerization).In this way components have been identified which form overall 86.0 per cent (m/m) of the low-boiling fraction.The said pyrolysis oil fraction has been found to contain almost 50 per cent (m/m) of unsaturated components able of polymerization, especially methylindenes, methyl-, ethyl- and dimethylvinylbenzenes, divinylbenzenes and 1,2-dihydronaphthalene.Elution behaviour of all the identified isomeric methylindenes, divinylbenzenes and 1,2-dihydronaphthalene has been evaluated by determination of parameters of the equation Ist.phase(2) = k.Ist.phase(1) + q. The Kovats elution indices of all the identified aromatic hydrocarbons have been determined with the use of a glass capilary column wetted with Carbowax 20M at 80o C.
Novrocik, Jan,Novrocikova, Marta
p. 60 - 70
(2007/10/02)