2-Thio derivatives of dUrd and 5-fluoro-dUrd and their 5'-monophosphates: synthesis, interaction with tumor thymidylate synthase, and in vitro antitumor activity

…, JM Dzik, M Balinska, W Rode, D Shugar

Index: Bretner; Kulikowski; Dzik; Balinska; Rode; Shugar Journal of Medicinal Chemistry, 1993 , vol. 36, # 23 p. 3611 - 3617

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Citation Number: 58

Abstract

TMS-2-thiouracil (l4) with 2-deoxy-3, 5-di-Op-toluyl-~-ribofuranosyl chloride (15) led to mixtures of the 8-and a-anomers of 3', 5'-toluylated 2'-deoxy-5-fluoro-2-thiouridine (16 and 18) or 2'-deoxy-2-thiouridine (17 and 191, each of which was deblocked with MeOH-NH3 to give the desired free anomeric nucleoside pairs 1, 5 and 3, 7, respectively. These were selectively converted to the corresponding 5'-monophosphates 2, 6 and 4, 8, with the aid ...