Synthesis and cytostatic evaluation of 4-N-alkanoyl and 4-N-alkyl gemcitabine analogues

J Pulido, AJ Sobczak, J Balzarini…

Index: Pulido, Jesse; Sobczak, Adam J.; Balzarini, Jan; Wnuk, Stanislaw F. Journal of Medicinal Chemistry, 2014 , vol. 57, # 1 p. 191 - 203

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Citation Number: 6

Abstract

The coupling of gemcitabine with functionalized carboxylic acids (C9–C13) or reactions of 4- N-tosylgemcitabine with the corresponding alkyl amines afforded 4-N-alkanoyl and 4-N-alkyl gemcitabine derivatives. The analogues with a terminal hydroxyl group on the alkyl chain were efficiently fluorinated under conditions that are compatible with protocols for 18F labeling. The 4-N-alkanoylgemcitabines showed potent cytostatic activities in the low ...