5-Substituted N 4-Hydroxy-2'-deoxycytidines and Their 5'-Monophosphates: Synthesis, Conformation, Interaction with Tumor Thymidylate Synthase, and in Vitro …

…, J Poznanski, M Bretner, T Kulikowski…

Index: Felczak; Miazga; Poznanski; Bretner; Kulikowski; Dzik; Golos; Zielinski; Ciesla; Rode Journal of Medicinal Chemistry, 2000 , vol. 43, # 24 p. 4647 - 4656

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Citation Number: 27

Abstract

Convenient procedures are described for the synthesis of 5-substituted N 4-hydroxy-2'- deoxycytidines 5a, b, dh via transformation of the respective 5-substituted 3', 5'-di-O-acetyl-2'- deoxyuridines 1a-c, eh. These procedures involved site-specific triazolation or N- methylimidazolation at position C (4), followed by hydroxylamination and deblocking with MeOH-NH3. Nucleosides 5a, b, dh were selectively converted to the corresponding 5'- ...