ChemInform Abstract: Nucleosides and Nucleotides. Part 154. New Neplanocin Analogues. Part 8. Synthesis and Biological Activity of 6′-C-Ethyl, -Ethenyl, and - Ethynyl Derivatives of Neplanocin A.

✍ Scribed by A. MATSUDA; ET AL. ET AL.

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 36 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199751273

✦ Synopsis

Nucleosides and Nucleotides. Part 154. New Neplanocin Analogues. Part 8. Synthesis and Biological Activity of 6'-C-Ethyl, -Ethenyl, and -Ethynyl Derivatives of Neplanocin A. -Reaction of the aldehyde (I) with ethynylmagnesium bromide gives the corresponding 6'-ethynyl derivative as a diastereomeric mixture (III) and (IV). Complete deprotection provides the 6'-ethynyl neplanocin A derivatives (VII) and (VIII) which can be separated by preparative chromatography. The corresponding 6'-ethenyl and 6'-ethyl derivatives of the (6'R)-and (6'S)-series are prepared by selective hydrogenation using Lindlar's catalyst. The endocyclic double bond remains intact under these conditions. The antiviral and inhibitory activity of the compounds on adenosylhomocysteine hydrolase is tested. The biological activity decreases in the order ethynyl ¿ ethenyl ¿ ethyl derivative. Moreover, the (6'R)-series is more reactive compared to the (6'S)-series. -(MATSUDA, A.