4′-fluorinated carbocyclic nucleosides:: Synthesis and inhibitory activity against S-adenosyl-L-homocysteine hydrolase

4 '-Fluorinated analogue of 9-[(1 ' R,2 ' S,3 ' R)-2 ',3 '-dihydroxy-eyelopentan-1 '-yl]adenine (DHCaA) and their related analogues were systematically synthesized under the Mitsunobu and palladium(O) coupling conditions followed by fluorination with inversion of the configuration by using diethylammosulfur trifluoride, respectively. 4 '-P-Fluoro DHCaA and 2-amino-4 '-alpha-fluoro DHCaA demonstrated slight inhibitory activity against human and Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase, respectively.(c) 2006 Elsevier Ltd. All rights reserved.