Exploration of the SAR of anti-invasive chalcones: Synthesis and biological evaluation of conformationally restricted analogues

被引：26

作者：

Roman, Bart I. ^{[1
]}

De Ryck, Tine ^{[2
]}

Dierickx, Laura ^{[1
]}

Vanhoecke, Barbara W. A. ^{[2
]}

Katritzky, Alan R. ^{[3
,4
]}

Bracke, Marc ^{[2
]}

Stevens, Christian V. ^{[1
]}

机构：

[1] Univ Ghent, Fac Biosci Engn, Dept Sustainable Organ Chem & Technol, Res Grp SynBioC, B-9000 Ghent, Belgium

[2] Ghent Univ Hosp, Dept Radiat Oncol & Expt Canc Res, Lab Expt Canc Res, B-9000 Ghent, Belgium

[3] Univ Florida, Ctr Heterocycl Cpds, Dept Chem, Gainesville, FL 32611 USA

[4] King Abdulaziz Univ, Dept Chem, Jeddah 21589, Saudi Arabia

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2012年 / 20卷 / 15期

基金：

比利时弗兰德研究基金会;

关键词：

Invasion; Cancer; Isoxazole; SAR; Chalcone; COMBRETASTATIN A-4 ANALOGS; AGENTS; DERIVATIVES; METASTASIS; POTENT;

D O I：

10.1016/j.bmc.2012.05.069

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

In order to get a clearer view on the active geometry of anti-invasive chalcones, we have prepared a number of isoxazoles and related substances as conformationally restrained mimics of 1,3-diarylpropenones, and also of (Z)-stilbenes. In vitro anti-invasive activity data for 3,5-isoxazoles and 4,5-isoxazoles, together with an in silico geometrical comparison, point towards an active conformation for chalcones more resembling their s-trans geometry than the s-cis counterpart. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：4812 / 4819

页数：8

共 24 条

[1]

[Anonymous], 2012, patent application, Patent No. [EP 12153062, 12153062]

[2]

[Anonymous], 2002, CHEMDRAW ULTR 7 0 1

[3]

[Anonymous], 2007, HYPERCHEM 8 0 3

[4]

Bracke ME, 2008, ANTI-CANCER AGENT ME, V8, P171