2-(Substituted phenyl)amino analogs of 1-methoxyspirobrassinol methyl ether: Synthesis and anticancer activity

被引：42

作者：

Kutschy, Peter ^{[1
]}

Salayova, Aneta ^{[1
]}

Curillova, Zuzana ^{[1
]}

Kozar, Tibor ^{[2
]}

Mezencev, Roman ^{[3
]}

Mojzis, Jan ^{[4
]}

Pilatova, Martina ^{[4
]}

Balentova, Eva ^{[1
]}

Pazdera, Pavel ^{[5
]}

Sabol, Marian ^{[6
]}

Zburova, Michaela ^{[1
]}

机构：

[1] Safarik Univ, Fac Sci, Inst Chem Sci, Dept Organ Chem, Kosice 04001, Slovakia

[2] Slovak Acad Sci, Inst Expt Phys, Dept Biophys, Kosice 04001, Slovakia

[3] Georgia Inst Technol, Sch Biol, Coll Sci, Atlanta, GA 30332 USA

[4] Safarik Univ, Fac Med, Dept Pharmacol, Kosice 04066, Slovakia

[5] Masaryk Univ, Dept Chem, Ctr Synth Sustainable Condit & Their Management, CS-61137 Brno, Czech Republic

[6] Safarik Univ, Fac Med, Dept Microbiol, Kosice 04066, Slovakia

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2009年 / 17卷 / 10期

关键词：

Phytoalexins; Spiroindolines; Anticancer activity; QSAR; CANCER CHEMOPREVENTIVE ACTIVITY; CRUCIFEROUS PHYTOALEXINS; CELL-LINES; BIOLOGICAL-ACTIVITY; BIOSYNTHESIS; BRASSICACEAE; BRASSININ; DATABASE; PHASE;

D O I：

10.1016/j.bmc.2009.03.064

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：

New analogs of indole phytoalexin 1-methoxyspirobrassinol methyl ether have been designed by replacement of its 2-methoxy group with 2-(substituted phenyl)amino group. Synthesized by spirocyclization methodology, trans- and cis-diastereoisomers of target compounds were isolated and evaluated as potential anticancer and antimicrobial agents. Their molecular geometries were refined by ab initio minimizations. Pharmacophore modeling and QSAR studies were performed in order to correlate their molecular structure and biological activity. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3698 / 3712

页数：15

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