Suppr超能文献

快速合成新型 4-(3'-吲哚基)恶唑并嘧啶及其抗癌活性。

An expeditious synthesis and anticancer activity of novel 4-(3'-indolyl)oxazoles.

机构信息

Chemistry Group, Birla Institute of Technology and Science, Pilani 333031, Rajasthan, India.

出版信息

Eur J Med Chem. 2010 Mar;45(3):1244-9. doi: 10.1016/j.ejmech.2009.12.024. Epub 2009 Dec 21.

Abstract

A series of 4-(3'-indolyl)oxazole congeners have been synthesized and studied for their cytotoxicity against six cancer cell lines. Reaction of 3-acetyl-1'-benzenesulfonylindole with [hydroxy(tosyloxy)iodo]benzene afforded pure 3-tosyloxyacetyl-1'-benzenesulfonylindole. Microwave-accelerated neat reaction of 3-tosyloxyacetyl-1-benzenesulfonylindole with amides resulted in the exclusive formation of 4-(1'-benzenesulfonylindol-3'-yl)-2-substituted oxazoles (4) in very good yield. Treatment of 4 with aqueous sodium hydroxide under refluxing conditions afforded pure 4-(3'-indolyl)-2-substituted oxazoles (5) in excellent yield. The 4-(3'-indolyl)oxazoles 5d and 11 were found to be most cytotoxic and selective against various cancer cell lines. Compounds 5g, 5j and 5l showed moderate anticancer activity.

摘要

已经合成了一系列 4-(3'-吲哚基)恶唑同系物,并研究了它们对六种癌细胞系的细胞毒性。3-乙酰-1'-苯磺酰基吲哚与[羟基(对甲苯磺酰氧基)碘]苯反应得到纯的 3-对甲苯磺酰氧基乙酰-1'-苯磺酰基吲哚。在微波促进的无溶剂条件下,3-对甲苯磺酰氧基乙酰-1-苯磺酰基吲哚与酰胺反应,以非常好的产率得到了 4-(1'-苯磺酰基吲哚-3'-基)-2-取代恶唑(4)。在回流条件下用氢氧化钠水溶液处理 4 得到了纯的 4-(3'-吲哚基)-2-取代恶唑(5),产率非常好。4-(3'-吲哚基)恶唑 5d 和 11 被发现对各种癌细胞系具有最强的细胞毒性和选择性。化合物 5g、5j 和 5l 表现出中等的抗癌活性。

文献AI研究员

20分钟写一篇综述,助力文献阅读效率提升50倍。

立即体验

用中文搜PubMed

大模型驱动的PubMed中文搜索引擎

马上搜索

文档翻译

学术文献翻译模型,支持多种主流文档格式。

立即体验