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

Kazuo OGAWA; Masahiro NISHII; Jin-ichiro INAGAKI; Fujio NOHARA; Tohru SAITO; Taisuke ITAYA; Tozo FUJII

doi:10.1248/cpb.40.1315

小川和男, 西井正廣, 稲垣甚一郎, 野原富士夫, 斎藤徹, 板谷泰助, 藤井澄三

著者情報

キーワード: phenacylation primary amine, condensation chloropyrimidinone-phenacylamine, cyclization nitro-phenacylamino, guanine 7-oxide 8, 9-disubstituted, debenzylation benzyl carbenium ion, antitumor activity

ジャーナルフリー

1992 年 40 巻 5 号 p. 1315-1317

DOI https://doi.org/10.1248/cpb.40.1315

詳細

抄録

The synthesis of 8-methylguanine 7-oxide (3) was accomplished via a "phenacylamine route", which started from condensation of α-(4-methoxybenzylamino)propiophenone (6), prepared by coupling of α-bromopropiophenone (4) and 4-methoxybenzylamine (5), with 2-amino-6-chloro-5-nitro-4(3H)-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.

責任著者(Corresponding author)

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