title: 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).
authors.affiliation: School of Chemistry, University of Hyderabad, Hyderabad 500 046, India. ramsc@uohyd.ernet.in
authors.forename: Dhevalapally B
authors.initials: DB
authors.lastname: Ramachary
authors.forename: Y Vijayendar
authors.initials: YV
authors.lastname: Reddy
authors.forename: Atoshi
authors.initials: A
authors.lastname: Banerjee
authors.forename: Sharmistha
authors.initials: S
authors.lastname: Banerjee
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016923:Cell Death / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D015497:HIV-1 / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D019380:Anti-HIV Agents; D013141:Spiro Compounds