Furanfurin and thiophenfurin: two novel tiazofurin analogs. Synthesis, structure, antitumor activity, and interactions with inosine monophosphate dehydrogenase

P Franchetti, L Cappellacci, M Grifantini…

Index: Franchetti, Palmarisa; Cappellacci, Loredana; Grifantini, Mario; Barzi, Anna; Nocentini, Giuseppe; et al. Journal of Medicinal Chemistry, 1995 , vol. 38, # 19 p. 3829 - 3837

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Citation Number: 80

Abstract

The syntheses of furan and thiophene analogues of tiazofurin (furanfurin and thiophenfurin, respectively) are described. Direct stannic chloride-catalyzed C-glycosylation of ethyl 3- furancarboxylate (6) or ethyl 34hiophencarboxylate (18) with 1, 2, 3, 5-tetra-O-acetyl-~- ribofuranose gave 2-and 5-glycosylated regioisomers, as a mixture of a-and 8-anomers, and the 8-2, 5-diglycosylated derivatives. Deprotection of ethyl 5-(2, 3, 5-tri-0-acetyl-B-~- ...