A new vinyl selenone-based domino approach to spirocyclopropyl oxindoles endowed with anti-HIV RT activity. Issue 6 (12th January 2016)

• Record Type: Journal Article
• Authors: Palomba, M.; Rossi, L.; Sancineto, L.; Tramontano, E.; Corona, A.; Bagnoli, L.; Santi, C.; Pannecouque, C.; Tabarrini, O.; Marini, F.
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 6(2016)
• Page Start: 2015
• Page End: 2024
• Publication Date: 2016-01-12
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob02451j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A flexible synthesis of spirocyclopropyl oxindoles from vinyl selenones and oxindoles via a domino Michael addition/proton transfer/cyclization sequence has been developed. Abstract : Herein, we disclose a general and flexible access to spirocyclopropyl oxindoles by a domino Michael/intramolecular nucleophilic substitution pathway with variously substituted vinyl selenones and enolizable oxindoles in aqueous sodium hydroxide solution. The spirocyclopropyl oxindole being a privileged scaffold, some of the synthesized compounds were selected for biological evaluation. Compound3m showed selective anti-HIV-1 activity thanks to its ability to inhibit the reverse transcriptase.