Enantioselective approach towards the synthesis of spiro-indeno [1,2-b] quinoxaline pyrrolothiazoles as antioxidant and antiproliferative

被引：38

作者：

Mani, Kailasam Saravana ^{[1
]}

Murugesapandian, Balasubramanian ^{[1
]}

Kaminsky, Werner ^{[2
]}

Rajendran, Subramaniam Parameswaran ^{[1
]}

机构：

[1] Bharathiar Univ, Dept Chem, Coimbatore, Tamil Nadu, India

[2] Univ Washington, Dept Chem, Seatle, WA 98195 USA

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 30期

关键词：

Spiro-indenoquinoxaline pyrrolothiazoles; Quinoline dipolarophile; Thiazolidine-2-carboxylic acid; Antioxidants; Antiproliferative; 3-COMPONENT 1,3-DIPOLAR CYCLOADDITION; HIGHLY FUNCTIONALIZED DISPIRO; BREAST-CANCER CELLS; STEREOSELECTIVE-SYNTHESIS; ANTIMYCOBACTERIAL ACTIVITY; COMBINATORIAL SYNTHESIS; HYBRID HETEROCYCLES; STEM-CELL; DERIVATIVES; ANTICANCER;

D O I：

10.1016/j.tetlet.2018.06.035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The 1,3-dipolar cycloaddition reactions of azomethine ylide generated in situ from indeno quinoxaline and thiazolidine-2-carboxylic acid to a series of quinoline bearing dipolarophile afforded novel spiro indeno-quinoxaline pyrrolo thiazoles in quantitative yields. The newly synthesized compounds were characterized using different spectroscopic techniques. Furthermore, the molecular structure of compound 5c was confirmed by single crystal X-ray crystallography. The synthesized compounds were screened for their in vitro antioxidant activity and in vitro cytotoxic activity against breast cancer cell line MCF-7 and adenocarcinomic cancer cell line A-549. Compound containing more electron donors in quinoline site were found to be more potent with good IC50 values. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：2921 / 2929

页数：9

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