Issue 21, 2011

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

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).

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

Supplementary files

Article information

Article type
Communication
Submitted
09 Jul 2011
Accepted
23 Aug 2011
First published
23 Aug 2011

Org. Biomol. Chem., 2011,9, 7282-7286

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

D. B. Ramachary, Y. V. Reddy, A. Banerjee and S. Banerjee, Org. Biomol. Chem., 2011, 9, 7282 DOI: 10.1039/C1OB06133J

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