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

H Lee; S I Lee; S I Yang

doi:10.1016/S0960-894X(98)00543-5

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

Bioorg Med Chem Lett. 1998 Nov 3;8(21):2991-4. doi: 10.1016/S0960-894X(98)00543-5.

Authors

H Lee¹, S I Lee, S I Yang

Affiliation

¹ College of Pharmacy, Chungbuk National University, Cheongju, Korea.

PMID: 9873661
DOI: 10.1016/S0960-894X(98)00543-5

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 cytotoxic activity comparable to that of doxorubicin.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anthraquinones / chemical synthesis*
Anthraquinones / pharmacology
Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / pharmacology
Humans
Structure-Activity Relationship
Tumor Cells, Cultured

Substances

Anthraquinones
Antineoplastic Agents