Carbocyclic nucleoside antitumor activity

Carbocyclic nucleoside analogues have also attracted considerable attention because of their antiviral and antitumor activities. Of particular interest are cyclohexenyl nucleosides, whose conformation resembles that of natural nucleosides. They can hybridize with nucleic acids and may therefore hold promise as components of antisense oligonucleotides.46-52... 

Neplanocins. Neplanocins A—D and F (37—41) are carbocyclic nucleoside antibiotic products of Ampullariella regularis (1,4) that are structurally related to (36) in that they contain either a cyclopentene or epoxy cyclopentane ring (121,122). The chemical syntheses of (37—41) and the 3-deazaneplanocins have been reported (123—126). Compound (37), which is converted to its 5 -triphosphate, has potent antitumor and antiviral activities (127—129). It strongly inhibits SAM in cells and viruses (128—131) and is converted to the 3 -keto derivative by Tadenosylhomocysteine hydrolase (132,133). 

Carbocyclic nucleosides are structural analogues of natural and synthetic nucleosides, which often exhibit powerful antitumor and antiviral activities. In the course of synthesising chiral members of this family of compounds, Castillon et al. have developed the DKR of a 3-hydroxymethyl-cyclopentanol intermediate as key step, providing the corresponding acetate which constituted the key intermediate of this synthesis. This DKR process was... 

Unsaturated and carbocyclic nucleoside analogues Synthesis, antitumor, and antiviral activity, J. Med. Chem. 34 421 (1991). 

R. Vince, J. Brownell, and S. Daluge, Carbocyclic analogues of xylofuranosylpurine nucleosides, synthesis and antitumor activity,/. Med. Chem. 27 1358 (1984). 

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