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Paper | Special issue | Vol 76, No. 1, 2008, pp.605-616
Published online, 17th April, 2008
DOI: 10.3987/COM-08-S(N)50
Design, Synthesis and Evaluation of Antitumor and Antiviral Activities of 5-Amino-1H-[1,2,3]triazolo[4,5-d]pyrimidin-7(6H)-ones (8-Azaguanines) and 7-Amino-1H-[1,2,3]triazolo[4,5-d]pyrimidin-5(4H)-ones (8-Azaisoguanines)

Rafiqul Islam, Noriyuki Ashida, and Tomohisa Nagamatsu*

*Department of Drug Discovery and Development, Division of Pharmaceutical Sciences, Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, Okayama University, Tsushima-naka, Okayama 700-8530, Japan

Abstract

Preparation of 5-amino-1H-[1,2,3]triazolo[4,5-d]pyrimidin-7(6H)-ones (5a-h) and 7-amino-1H-[1,2,3]triazolo[4,5-d]pyrimidin-5(4H)-ones (8a-n) was accomplished by nitrosative cyclization of the desired 2,5,6-triaminopyrimidine (2a-h) and 4,5,6-triaminopyrimidine derivatives (7a-n) with nitrous acid, respectively. Compounds 5a-h were also prepared by nucleophilic replacement of the methylthio group of 5-methylthio-1H-[1,2,3]triazolo[4,5-d]pyrimidin-7(6H)-one (4) by appropriate amines. Similarly, some 7-amino derivatives (10a-i) were synthesized by replacement of the thiol groups of the 7-thiol derivative (9) by appropriate amines. Antitumor and antiviral activities of the synthesized compounds were evaluated in vitro.