2H-chromene derivatives bearing thiazolidine-2,4-dione, rhodanine or hydantoin moieties as potential anticancer agents

被引：190

作者：

Azizmohammadi, Mohammad ^{[1
]}

Khoobi, Mehdi ^{[2
,3
]}

Ramazani, Ali ^{[1
]}

Emami, Saeed ^{[4
,5
]}

Zarrin, Abdolhossein ^{[6
]}

Firuzi, Omidreza ^{[6
]}

Miri, Ramin ^{[6
]}

Shafiee, Abbas ^{[2
,3
]}

机构：

[1] Zanjan Univ, Dept Chem, Zanjan, Iran

[2] Univ Tehran Med Sci, Dept Med Chem, Fac Pharm, Tehran 14176, Iran

[3] Univ Tehran Med Sci, Pharmaceut Sci Res Ctr, Tehran 14176, Iran

[4] Mazandaran Univ Med Sci, Fac Pharm, Dept Med Chem, Sari, Iran

[5] Mazandaran Univ Med Sci, Pharmaceut Sci Res Ctr, Fac Pharm, Sari, Iran

[6] Shiraz Univ Med Sci, Med & Nat Prod Chem Res Ctr, Shiraz, Iran

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 59卷

基金：

美国国家科学基金会;

关键词：

Anti-cancer agents; Cytotoxicity; 2H-chromene; Thiazolidine-2,4-dione; Rhodanine; Hydantoin; ANTIPROLIFERATIVE ACTIVITY; CYTOTOXIC ACTIVITY; CANCER; 5-BENZYLIDENE-HYDANTOINS; INHIBITORS; APOPTOSIS; ANALOGS; CELLS;

D O I：

10.1016/j.ejmech.2012.10.044

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A variety of (Z)-[(2H-chromen-3-yl)methylene]azolidinones 6a-t bearing thiazolidine-2,4-dione, rhodanine or hydantoin scaffolds were designed and synthesized as potential anticancer agents. Inhibitory effect of synthesized compounds 6a-t on the viability of cancer and non-cancer cells was assessed using MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) reduction assay. The SAR study revealed that the N-substitution of azolidinone moiety cannot improve the activity but S/NH replacement (thiazolidine-2,4-dione/hydantoin) and S/O alteration (rhodanine/thiazolidine-2,4-dione) enable us to modulate the growth inhibition activity against various cell lines. Moreover, 6-bromo and 2-methyl substituents on chromene ring had positive effects on growth inhibitory activity depending on the tumor cell lines. Among the synthesized compounds, hydantoin derivative 60 with a 6-bromo-2-methyl-2H-chromene substructure showed the best profile of cytotoxicity comparable to that of cisplatin as standard anticancer agent. (C) 2012 Elsevier Masson SAS. All rights reserved.

引用

页码：15 / 22

页数：8

共 33 条

[21] Sulfur and selenium derivatives of quinazoline and pyrido[2,3-d]pyrimidine: Synthesis and study of their potential cytotoxic activity in vitro [J].