A Novel Methodology for Synthesis of 1,5,6-Trisubstituted 2(1H)-Pyrazinones of Biological Interest

被引：6

作者：

Saijo, Ryosuke ^{[1
]}

Sekiya, Hiroshi ^{[2
,3
]}

Tamai, Eiji ^{[2
]}

Kurihara, Ken-ichi ^{[1
]}

Maki, Jun ^{[2
]}

Sakagami, Hiroshi

Kawase, Masami ^{[1
]}

机构：

[1] Matsuyama Univ, Fac Pharmaceut Sci, Matsuyama, Ehime 7908578, Japan

[2] Matsuyama Univ, Coll Pharmaceut Sci, Dept Infect Dis, Matsuyama, Ehime 7908578, Japan

[3] Meikai Univ, Sch Dent, Div Pharmacol, Sakado, Saitama 3500283, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2017年 / 65卷 / 04期

基金：

日本学术振兴会;

关键词：

ring transformation; mesoionic; pyrazinone; isocyanide; RING TRANSFORMATION; CONVENIENT SYNTHESIS; INHIBITORY-ACTIVITY; DERIVATIVES; DISCOVERY; YLIDES;

D O I：

10.1248/cpb.c16-00830

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

In this report, we describe a new method for the synthesis of densely functionalized 2(1H)-pyrazinones. Treatment of mesoionic 1,3-oxazolium-5-olates with carbanions derived from activated methylene isocyanides (p-toluenesulfonylmethyl isocyanide (TosMIC) and ethyl isocyanoacetate) causes a novel ring transformation affording 2(1H)-pyrazinones in moderate to high yields. The cytotoxicity and antibacterial activity of some of the obtained products were studied and some of the products exhibited tumor-specific cytotoxicity.

引用

页码：365 / 372

页数：8

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