56766-77-9Relevant articles and documents
Biomimetic regioselective and high-yielding Cu(i)-catalyzed dimerization of sinapate esters in green solvent Cyrene: Towards sustainable antioxidant and anti-UV ingredients
Mention, Matthieu M.,Flourat, Amandine L.,Peyrot, Cédric,Allais, Florent
supporting information, p. 2077 - 2085 (2020/04/08)
Naturally occurring sinapic acid and its esters are anti-UV and antiradical chemicals. This work aimed at designing an industrially relevant sustainable synthetic pathway allowing their selective β-β′ dimerization to enhance their properties with a view to use them in commercial applications such as functional additives for cosmetics, plastics and food/feed. A copper(i)-catalyzed procedure involving pyridine and O2 from air was developed and greened up using the REACH-compliant bio-based solvent Cyrene. Upon optimizing further through design of experiments, this sustainable synthetic process was successfully implemented to various sinapate esters and was validated on the multigram scale. Antiradical activities of the resulting β-β′ disinapate esters were benchmarked against commercial antioxidants, whereas their UV absorbance was compared to that of sinapoyl malate, a natural anti-UV compound found in plants and that of Octinoxate, a widely used commercial sunscreen ingredient. Results showed that these dimers were better radical scavengers, and not only exhibited a better UV absorbance but also covered both UV-A and UV-B regions.
Development of catalytic deacylative alkylations (DaA) of 3-acyl-2-oxindoles: total synthesis of meso-chimonanthine and related alkaloids
Kumar, Nivesh,Das, Mrinal Kanti,Ghosh, Santanu,Bisai, Alakesh
supporting information, p. 2170 - 2173 (2017/02/19)
We present an effective deacylative alkylation strategy for the construction of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudobenzylic position. A wide variety of products with quaternary centers could be accessed by employing simple Pd(0) catalysis under mild reaction conditions. Importantly, the same strategy works equally well for the dimeric 2-oxindole system, furnishing products with a vicinal quaternary center in favour of meso-isomer as the major product. Eventual application to the total syntheses of meso-chimonanthine and meso-folicanthine very well demonstrates the synthetic potential of this strategy.
Synthesis and antitumor activity of feruloyl and caffeoyl derivatives This paper is dedicated to Prof. Wei-xiao Hu for his lifelong commitment to mentoring graduate students
Chen, Hui-Zhen,Chen, You-Bao,Lv, Ya-Ping,Zeng, Fang,Zhang, Juan,Zhou, Yong-Lie,Li, Han-Bing,Chen, Li-Fei,Zhou, Bin-Jie,Gao, Jian-Rong,Xia, Chun-Nian
supporting information, p. 4367 - 4371 (2015/02/06)
We developed two efficient protocols for the synthesis of feruloyl and caffeoyl derivatives from commercial vanillin and veratraldehyde. Pharmacological activities were assessed against a panel of human cancer cell lines in vitro. Most synthesized compounds demonstrated attractive cytotoxicity. Several new compounds demonstrated significant antiproliferative and cytotoxic activities against HeLa and Bewo tumor cell lines. In particular, 5-nitro caffeic adamantyl ester showed broad spectrum of tumor inhibition in 10 cell lines, and reduced tumor weight by 36.7% in vivo when administered at a dose of 40 mg kg-1.
One-pot preparation of phenylpropanoid esters co-catalyzed by boric acid and piperidine
Wang, Huan,Wei, Qing-Yi,Jiang, Hong,Jiang, Zhen-Hua
experimental part, p. 207 - 213 (2012/05/20)
Phenylpropanoid esters, especially those with hydroxyl and/or methoxy groups on the benzene ring, are important medicinal chemicals or intermediates. They are usually prepared by esterification of their corresponding substituted cinnamic acids with various alcohols. However, the esterification procedures often suffer from environmentally hazardous problems when sulfuric acid is used as a catalyst or suffer from unsatisfactory yields and expensive raw material when enzyme is applied as a catalyst. In this paper, a convenient one-pot process for preparing various phenylpropanoid esters from substituted benzaldehydes bearing hydroxyl and/or methoxyl groups has been developed. The alcohols react first with malonic acid catalyzed by boric acid to form monomalonate, then without separation, let the resultant mixture immediately react with the injected various substituted benzaldehydes in the presence of piperidine to afford the desired esters with moderate to good yields. Springer Science+Business Media B.V. 2011.
Development of an enantioselective, kilogram-scale, rhodium-catalysed 1,4-addition
Brock, Sally,Hose, David R.J.,Moseley, Jonathan D.,Parker, Alexandra J.,Patel, Ian,Williams, Andrew J.
, p. 496 - 502 (2013/01/03)
A rhodium-catalysed 1,4-addition of an arylboron species to an α,β-unsaturated ester was the key chirality-inducing step in the synthesis of an API. We describe herein the development of this chemistry, including optimization of reagent charges, reaction
Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines
Xia, Chun-nian,Li, Hai-bo,liu, Feng,Hu, Wei-xiao
supporting information; experimental part, p. 6553 - 6557 (2009/09/06)
Forty caffeate analogues were synthesized via a convenient method starting from vanillin with moderate to good yields. The testing of biological activity of these compounds against HIV-1 integrase indicates that four compounds: bornyl caffeate, bornyl 2-nitrocaffeate, 5-nitrocaffeic acid and 5-nitrocaffeic acid phenethyl ester (5-nitroCAPE) possess a good HIV integrase inhibitory activity, IC50 19.9, 26.8, 25.0 and 13.5 μM, respectively. Twelve caffeate analogues were tested by MTT assay on growth of human hepatocellular carcinoma BEL-7404, human breast MCF-7 adenocarcinoma, human lung A549 adenocarcinoma and human gastric cancer BCG823 cell lines, respectively. And the best result is IC50 5.5 μM for CAPE against BEL-7404.
One-pot preparation of caffeic acid esters from 3,4-dihydroxybenzaldehyde
Hu, Wei-Xiao,Xia, Chun-Nian,Wang, Guo-Hong,Zhou, Wei
, p. 586 - 588 (2007/10/03)
A convenient one-pot process for preparing various esters of caffeic acid from 3,4-dihydroxybenzaldehyde has been developed. The alcohols or phenols react with Meldrum's acid to form malonic acid mono-esters, which, without separating, immediately react with 3,4-dihydroxybenzaldehyde to afford the desired esters in good yield. The 1H NMR data and X-ray diffraction analyses indicate that these α,β-unsaturated esters are in trans (E) form in accord with natural esters.
HETEROCYCLIC ANTI-VIRAL COMPOUNDS COMPRISING METABOLIZABLE MOIETIES AND THEIR USES
-
Page/Page column 53, (2010/02/14)
The present invention relates to substituted prodrug and compositions thereof useful for treating or preventing Hepatitis C virus (HCV) infections. In particular, the present invention relates to prodrugs of substituted diphenyl-, diheteroaryl- and mixed phenyl heteroaryl substituted five-membered heterocycle compounds, compositions comprising the compounds and the use of such compounds and compositions to inhibit HCV replication and/or proliferation as a therapeutic approach towards the treatment and/or prevention of HCV infections in humans and animals.
Synthesis of bone-targeted oestrogenic compounds for the inhibition of bone resorption
Bulman Page, Philip C,Moore, Jonathan P.G,Mansfield, Ian,McKenzie, Michael J,Bowler, Wayne B,Gallagher, James A
, p. 1837 - 1847 (2007/10/03)
Syntheses have been realised for several members of a new class of potential bone resorption inhibitors consisting of steroidal oestrogenic compounds linked at the 17 position to a geminal bis(phosphonic acid) moiety through an ester linkage. The approach used has the potential to allow other biologically active compounds to be coupled to the geminal bisphosphonate unit.
Process for preparing malonic monoester
-
, (2008/06/13)
A malonic monoester is prepared in a good yield by a single step reaction by reacting malonic acid with an alcohol in the presence of a base and an activator of malonic acid selected from the group consisting of an acyl halide or halocarbonate and an acid anhydride or dicarbonate.
