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.
H Lee  1 ,  S I Lee ,  S I Yang
Affiliations
  • 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.