Synthesis, structure, and antiproliferative activity of selenophenfurin, an inosine 5'-monophosphate dehydrogenase inhibitor analogue of selenazofurin

P Franchetti, L Cappellacci, GA Sheikha…

Index: Franchetti, Palmarisa; Cappellacci, Loredana; Sheikha, Ghassan Abu; Jayaram, Hiremagalur N.; Gurudutt, Vivek V.; Sint, Thaw; Schneider, Bryan P.; Jones, William D.; Goldstein, Barry M.; Perra, Graziella; De Montis, Antonella; Loi, Anna Giulia; La Colla, Paolo; Grifantini, Mario Journal of Medicinal Chemistry, 1997 , vol. 40, # 11 p. 1731 - 1737

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Citation Number: 66

Abstract

The synthesis and biological activity of selenophenfurin (5-β-d-ribofuranosylselenophene-3- carboxamide, 1), the selenophene analogue of selenazofurin, are described. Glycosylation of ethyl selenophene-3-carboxylate (6) under stannic chloride-catalyzed conditions gave 2- and 5-glycosylated regioisomers, as a mixture of α-and β-anomers, and the β-2, 5- diglycosylated derivative. Deprotected ethyl 5-β-d-ribofuranosylselenophene-3- ...