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

• Published in: Chemical & pharmaceutical bulletin Vol. 40; no. 5; pp. 1315 - 1317
• Main Authors: OGAWA, Kazuo, NISHII, Masahiro, INAGAKI, Jin-ichiro, NOHARA, Fujio, SAITO, Tohru, ITAYA, Taisuke, FUJII, Tozo
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 1992; Maruzen; Japan Science and Technology Agency
• Subjects: Animals; Antibiotics, Antineoplastic - chemical synthesis; Antibiotics, Antineoplastic - pharmacology; antitumor activity; Chemistry; condensation chloropyrimidinone-phenacylamine; cyclization nitro-phenacylamino; debenzylation benzyl carbenium ion; Exact sciences and technology; Guanine - analogs & derivatives; Guanine - chemical synthesis; Guanine - pharmacology; guanine 7-oxide 8, 9-disubstituted; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Methylation; Mice; Organic chemistry; phenacylation primary amine; Preparations and properties; Purines - chemical synthesis; Purines - pharmacology; Antineoplastic agent; L5178Y-Leukemia; Purine derivatives; Nitrogen heterocycle; Nitrone; Bicyclic compound; In vitro; Biological activity; Sulfonate
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.40.1315

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.