Synthesis and interaction with uridine phosphorylase of 5'-deoxy-4', 5-difluorouridine, a new prodrug of 5-fluorouracil

S Ajmera, AR Bapat, PV Danenberg…

Index: Ajmera; Bapat; Stephanian; Danenberg Journal of Medicinal Chemistry, 1988 , vol. 31, # 6 p. 1094 - 1098

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Citation Number: 28

Abstract

5'-Deoxy-4', 5-difluorouridine (4'-F-5'-dFUrd)(10) has been synthesized on the basis of the rationale that the labilization of the glycosidic linkage caused by the 4'-flUOrO substituent might allow this compound to be a better prodrug form of the anticancer drug 5-fluorouracil (FUra) than is the widely studied fluoropyrimidine 5'-deoxy-5-fluorouridine (5'-dFUrd). The rate of solvolytic hydrolysis of the glycosidic linkage of 4'-F-5'-dFUrd at pH 1 was about ...