Synthetic nucleosides and nucleotides. X. Synthesis and biological activities of several purin-6-yl benzyl disulfides and their ribonucleosides

Abstract

Reaction of S-benzylthioisothiouronium hydrochloride with 6-mercaptopurine (1), 9-Β-D-ribofuranosyl-6-mercaptopurine (2), 6-thioguanine (3) and 9-Β-D-ribofuranosy 1-6-thioguanine (4) afforded corresponding benzyl disulfide derivatives (5—8) in good yield. These compounds were converted easily to parent mercapto derivatives when they were treated with various reducing agents such as Β mercaptoethanol. Antitumor activity of compound 5 was higher than that of 1 both in ascites Sarcoma 180 and in Nakahara-Fukuoka sarcoma systems. However, toxicity and immunosuppressive activity of compound 5 and 6 were higher than those of 1 and 2, respectively. © 1978, The Pharmaceutical Society of Japan. All rights reserved.