Lipophilic 5'-alkyl phosphate esters of 1-. beta.-D-arabinofuranosylcytosine and its N4-acyl and 2, 2'-anhydro-3'-O-acyl derivatives as potential prodrugs

A Rosowsky, SH Kim, J Ross…

Index: Rosowsky, A.; Kim, S.-H.; Ross, J.; Wick, M. M. Journal of Medicinal Chemistry, 1982 , vol. 25, # 2 p. 171 - 178

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Citation Number: 50

Abstract

Lipophilic 5'-(alkyl phosphate) esters of l-0-D-arabinofuranosylcytosine (ara-C) and several N4-acyl and 3'-0-acyl-2, 2'-anhydro derivatives of ara-C were synthesized as potential prodrugs of ara-C 5'-monophosphate (ara-CMP). Alkylphosphorylation of ara-C, N4- palmitoyl-ara-C, and N4-stearoyl-ara-C was achieved in a single continuous operation by allowing the nucleoside to react with POCl, in trimethyl or triethyl phosphate and adding ...