Cyclopropyl and Related Analogs of the Anti-HIV Compound, Isodideoxyadenosine

Abstract

Novel 3′-substituted isonucleoside analogs were designed on the basis of the similarities of their electrostatic potential with the active anti-HIV compound, (S,S)-isodideoxy-adenosine. The key synthetic step involved coupling between the dideoxygenated sugar derivatives, 10 and 14, and adenine under Mitsunobu conditions. Anti-HIV data are mentioned.

Key Words:

• Isonucleosides
• Electrostatic potential
• Synthesis
• Antiviral

Acknowledgments

The project described was supported by Grant Number AI 32851 from the National Institutes of Health. Its contents are solely the responsibility of the authors and do not necessarily represent the official views of the NIH. We thank Drs. Erik De Clercq and Jan Balzarini for the antiviral evaluations.