84002-48-2Relevant academic research and scientific papers
NOVEL ANALOGUES OF EPICATECHIN AND RELATED POLYPHENOLS
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, (2016/03/05)
The present invention provides novel analogues of epicatechin and related polyphenols, their variously functionalized derivatives, process for preparation of the same, composition comprising these compounds and their method of use.
An efficient total synthesis of resokaempferol 3-O-β-D-glucoside
Ren, Xuhong,Wang, Jingjing,Shen, Liu-Lan,Li, Wei,Muraoka, Osamu,Cheng, Maosheng
supporting information; experimental part, p. 1135 - 1137 (2011/11/30)
Resokaempferol 3-O-β-D-glucoside, an artificial flavonol glycoside, was synthesized from 2,4-dihydroxyacetophenone in six steps and 40% overall yield via an efficient glycosylation method using NaH.
Acidic rearrangement of (benzyloxy)chalcones: A short synthesis of chamanetin
Sagrera, Gabriel,Seoane, Gustavo
, p. 4190 - 4202 (2011/03/20)
Treatment of (benzyloxy)chalcones with trifluoroacetic acid in refluxing chloroform gave several new benzyl(hydroxy)flavanones in high yields and good regioselectivities. By using this procedure, we prepared the natural compound chamanetin in good yield from readily available reagents. Georg Thieme Verlag Stuttgart - New York.
Enantioselective synthesis of flavan-3-ols using a mitsunobu cyclization
Krohn, Karsten,Ahmed, Ishtiaq,John, Markus
scheme or table, p. 779 - 786 (2009/09/06)
The synthesis of four flavan-3-ols with different substitution patterns and electron densities has been achieved in high stereo- and regioselectivity by a one-step Mitsunobu reaction from the corresponding diols, which were prepared by enantioselective Sharpless dihydroxylation of suitable olefins. The six-membered flavan-3-ols were the only cyclization products and the theoretically possible formation of five-membered rings during the Mitsunobu cyclization was not observed. The flavanols are important starting materials for the synthesis of dimers such as the procyanidins or other coupling products such as the flavan part of the potent DNA polymerase β inhibitor myristinin A. The enantioselectivities of both the Sharpless dihydroxylation and the Mitsunobu cyclization steps were monitored by chiral HPLC. Georg Thieme Verlag Stuttgart New York.
Simplified YM-26734 inhibitors of secreted phospholipase A2 group IIA
Oslund, Rob C.,Cermak, Nathan,Verlinde, Christophe L.M.J.,Gelb, Michael H.
supporting information; experimental part, p. 5415 - 5419 (2009/05/30)
Simplified analogs of YM-26734, a known inhibitor of secreted phospholipase A2 (sPLA2) group IIA, were synthesized and found to also display potent inhibition at low nanomolar concentrations. Analogs were based on the didodecanoylphl
Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure-activity relationships
Cabrera, Mauricio,Simoens, Macarena,Falchi, Gabriela,Lavaggi, M. Laura,Piro, Oscar E.,Castellano, Eduardo E.,Vidal, Anabel,Azqueta, Amaia,Monge, Antonio,de Cerain, Adela Lopez,Sagrera, Gabriel,Seoane, Gustavo,Cerecetto, Hugo,Gonzalez, Mercedes
, p. 3356 - 3367 (2008/02/07)
A series of synthetic chalcones, flavanones, and flavones has been synthesized and evaluated for antitumor activity against the human kidney carcinoma cells TK-10, human mammary adenocarcinoma cells MCF-7 (estrogen receptor-positive), and human colon adenocarcinoma cells HT-29. The most active series is the chalcone ones with the best results against TK-10 and HT-29 cells. Fourteen out of 53 analyzed compounds resulted very active against at least two of the studied tumoral cells. Alkaline single cell gel electrophoresis, comet assay, was performed as a study of the chromosomal aberrations promoted by the compounds on normal cells. Four active and two inactive chalcones were studied in the comet assay against normal human kidney cells (HK-2). A structure-activity relationship analysis of these compounds was performed and for 4- and 3,4-disubstituted derivatives a quantitative correlation was obtained in the case of anti-HT-29 activity.
(+)-Myristinin A, a naturally occurring DNA polymerase β inhibitor and potent DNA-damaging agent
Maloney, David J.,Deng, Jing-Zhen,Starck, Shelley R.,Gao, Zhijie,Hecht, Sidney M.
, p. 4140 - 4141 (2007/10/03)
The first stereoselective total synthesis of the naturally occurring flavan myristinin A has been accomplished, as well as its biochemical evaluation. This synthesis verified the structural assignment and allowed for the determination of the absolute ster
4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity
De Meyer,Haemers,Mishra,Pandey,Pieters,Vanden Berghe,Vlietinck
, p. 736 - 746 (2007/10/02)
4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5 μg/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.
