Synthesis, anti-cancer and anti-inflammatory activity of novel 2-substituted isoflavenes

被引：5

作者：

Eiffe, Eleanor ^{[1
]}

Pasquier, Eddy ^{[2
,3
]}

Kavallaris, Maria ^{[2
,4
]}

Herbert, Cristan ^{[5
]}

Black, David StC ^{[1
]}

Kumar, Naresh ^{[1
]}

机构：

[1] Univ New S Wales, Sch Chem, Sydney, NSW 2052, Australia

[2] Univ New S Wales, Childrens Canc Inst Australia Med Res, Lowy Canc Res Ctr, Randwick, NSW 2052, Australia

[3] Metron Global Hlth Initiat, Marseille, France

[4] UNSW, Australian Ctr Nanomed, Sch Chem Engn, Sydney, NSW 2052, Australia

[5] Univ New S Wales, Sch Med Sci, Sydney, NSW 2052, Australia

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2014年 / 22卷 / 19期

基金：

英国医学研究理事会; 澳大利亚研究理事会;

关键词：

Isoflavonoid; Isoflavene; Isoflavylium; Nucleophilic addition; Anti-cancer; Anti-inflammatory; INDEPENDENT CELL-DEATH; CANCER; GENISTEIN; DAIDZEIN; PHENOXODIOL; FLAVONOIDS; CHEMISTRY; BETA;

D O I：

10.1016/j.bmc.2014.08.010

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：

Fifteen novel 2-substituted isoflavenes were synthesised via nucleophilic addition to isoflavylium salts. Twelve of the newly synthesised isoflavenes, along with the unsubstituted parent isoflavene, were tested in cell viability assays against the SHEP neuroblastoma and MDA-MB-231 breast adenocarcinoma cell lines. While the 2-substituted isoflavenes displayed a range of anti-proliferative activities, in most cases they were less active that the unsubstituted isoflavene (IC50 = 9.9 mu M vs SHEP; IC50 = 33 mu M vs MDA-MB-231). However, compound 7f, derived from the reaction between isoflavylium salt 5 and para-methoxyacetophenone, showed improved anti-proliferative activity against breast cancer cells (IC50 = 7.6 mu M). Furthermore, compound 7f, as well as analogues 7a, 7c, 11d and 14, inhibited the production of interleukin-6 in LPS-activated RAW 264.7 cells. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：5182 / 5193

页数：12

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