Design, synthesis and biological evaluation of optically pure functionalized spiro[5,5]undecane-1,5,9-triones as HIV-1 inhibitors

Dhevalapally B Ramachary; Y Vijayendar Reddy; Atoshi Banerjee; Sharmistha Banerjee

doi:10.1039/c1ob06133j

Design, synthesis and biological evaluation of optically pure functionalized spiro[5,5]undecane-1,5,9-triones as HIV-1 inhibitors

Org Biomol Chem. 2011 Nov 7;9(21):7282-6. doi: 10.1039/c1ob06133j. Epub 2011 Sep 14.

Authors

Dhevalapally B Ramachary¹, Y Vijayendar Reddy, Atoshi Banerjee, Sharmistha Banerjee

Affiliation

¹ School of Chemistry, University of Hyderabad, Hyderabad 500 046, India. ramsc@uohyd.ernet.in

PMID: 21915419
DOI: 10.1039/c1ob06133j

Abstract

A single-step amino acid-catalyzed diastereoselective three-component synthesis of optically pure highly functionalized spiro[5,5]undecane-1,5,9-triones preferentially over the four stereoisomers was accomplished in very good yields with >99% ee/de. Preliminary cell culture-based in vivo screening on these molecules revealed that cis-1aca and cis-1jca are better lead compounds for HIV-1 treatment than the known antiretroviral drug azidothymidine (AZT).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anti-HIV Agents / chemical synthesis*
Anti-HIV Agents / chemistry
Anti-HIV Agents / pharmacology*
Cell Death / drug effects
Cell Survival / drug effects
Dose-Response Relationship, Drug
Drug Design*
HIV-1 / drug effects*
Microbial Sensitivity Tests
Molecular Structure
Spiro Compounds / chemical synthesis*
Spiro Compounds / chemistry
Spiro Compounds / pharmacology*
Stereoisomerism
Structure-Activity Relationship

Substances

Anti-HIV Agents
Spiro Compounds