Purines: LII: 1} Synthesis and Biological Evaluation of 8-Methylguanine 7-Oxide and Its 9-Arylmethyl Derivatives

Abstract

The synthesis of 8-methylguanine 7-oxide (3) was accomplished via a “phenacylamine route” which started from condensation of a-(4-methoxybenzylamino)propiophenone (6), prepared by coupling of a-bromopropiophenone (4) and 4-methoxybenzylamine (5), with 2-amino-6-chloro-5-nitro-4(311)-pyrimidinone (7) and proceeded through cyclization of the resulting phenacylaminopyrimidinone (8) and removal of the 4-methoxybenzyl group. The N-oxide 3 and its 9-arylmethyl derivatives 9 and 11 showed only very weak antileukemic activity and no antimicrobial activity. © 1992, The Pharmaceutical Society of Japan. All rights reserved.