Synthesis and in vitro cytotoxicity of 3-substituted-1, 8-diazaanthraquinones produced by Lewis-acid catalyzed hetero Diels-Alder reaction

H Lee, SI Lee, SI Yang

Index: Lee, Heesoon; Lee, Seung-Il; Yang, Sung-Il Bioorganic and Medicinal Chemistry Letters, 1998 , vol. 8, # 21 p. 2991 - 2994

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Citation Number: 14

Abstract

A hetero Diels-Alder reaction of quinoline-5, 8-dione with 1-(N, N-dimethylamino)-3-methyl-1- aza-1, 3-butadiene proceeded to give 3-methyl-1, 8-diazaanthraquinone (100% regioselectivity) in the presence of Lewis-acid catalyst (ZnCl2 or ZnBr2). Subsequent functionalizations of the benzylic methyl group resulted in the 1, 8-diazaanthraquinone analogues as potential antitumor agents. The most active compound, 8, exhibited in vitro ...