Synthesis and Antitumor Activity of Some Novel 5,6,7,8-Tetrahydro- benzo-thieno[2,3-d]pyrimidin-4(3H)-one Derivatives

doi:10.6023/cjoc201410035

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (5): 1075-1080.DOI: 10.6023/cjoc201410035 Previous Articles Next Articles

ARTICLE

新型5,6,7,8-四氢苯并噻吩并嘧啶酮衍生物的合成与抗肿瘤活性研究

王红梅^a, 郭树兵^b, 胡扬根^a,c, 曾小华^a, 杨光义^a,c

a 武当特色中药研究湖北省重点实验室湖北医药学院医学化学研究所十堰 442000;
b 湖北医药学院图书馆十堰 442000;
c 湖北医药学院附属太和医院药学部十堰 442000

收稿日期:2014-10-24 修回日期:2015-12-15 发布日期:2015-01-05
通讯作者: 胡扬根, 杨光义 E-mail:huyg@hbmu.edu.cn;ygy999@163.com
基金资助:
湖北自然科学基金(No.2011CDC006)、湖北省2011协同创新中心基金(No.2011JH-2014CXTT07)和湖北医药学院优秀中青年科技创新团队研究(Nos.2011CXX03,2009QDJ15,2014XKJSXJ06)资助项目.

Synthesis and Antitumor Activity of Some Novel 5,6,7,8-Tetrahydro- benzo-thieno[2,3-d]pyrimidin-4(3H)-one Derivatives

Wang Hongmei^a, Guo Shubing^b, Hu Yanggen^a,c, Zeng Xiaohua^a, Yang Guangyi^a,c

a Hubei Key Laboratory of Wudang Local Chinese Medicine Research and Institute of Medicinal Chemistry, Hubei University of Medicine, Shiyan 442000;
b The Library of Hubei University of Medicine, Shiyan 442000;
c Department of Pharmacy, Taihe Hospital of Hubei University of Medicine, Shiyan 442000

Received:2014-10-24 Revised:2015-12-15 Published:2015-01-05
Supported by:
Project supported by the Natural Science Foundation of Hubei Province (No.2011CDC006), the Fund of Hubei 2011 Cooperative Innovation Center (No.2011JH-2014CXTT07) and the Science and Technology Innovation team Project of Hubei University of Medicine (Nos.2011CXX03, 2009QDJ15, 2014XKJSXJ06).

1. Synthesis and Antitumor Activity of Some Novel 5,6,7,8-Tetrahydro- benzo-thieno[2,3-d]pyrimidin-4(3H)-one Derivatives.PDF(2780KB)

Abstract

The aza-Wittig reaction of iminophosphorane 2 with alkyl isocyanates gave carbodiimides 3, which were allowed to react with various nucleophilic reagents under mild condition in satisfactory yields to prepare a novel series of 5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one derivatives. The structures of these compounds were confirmed by ¹H NMR, IR, MS and elemental analysis. The in vitro antitumor activities of compounds were analyzed with 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazo-liumbromide (MTT) standard method, 5d stood out as the most potent showing an IC₅₀ of 19.0 μmol/L against human tumor cell lines (KB).

Key words: aza-Wittig reaction, thieno[2,3-d]pyrimidin-4(3H)-ones, synthesis, antitumor

Cite this article

Wang Hongmei, Guo Shubing, Hu Yanggen, Zeng Xiaohua, Yang Guangyi. Synthesis and Antitumor Activity of Some Novel 5,6,7,8-Tetrahydro- benzo-thieno[2,3-d]pyrimidin-4(3H)-one Derivatives[J]. Chin. J. Org. Chem., 2015, 35(5): 1075-1080.

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新型5,6,7,8-四氢苯并噻吩并嘧啶酮衍生物的合成与抗肿瘤活性研究

Synthesis and Antitumor Activity of Some Novel 5,6,7,8-Tetrahydro- benzo-thieno[2,3-d]pyrimidin-4(3H)-one Derivatives

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