A new vinyl selenone-based domino approach to spirocyclopropyl oxindoles endowed with anti-HIV RT activity

• Published in: Organic & biomolecular chemistry Vol. 14; no. 6; p. 2015
• Main Authors: Palomba, M, Rossi, L, Sancineto, L, Tramontano, E, Corona, A, Bagnoli, L, Santi, C, Pannecouque, C, Tabarrini, O, Marini, F
• Format: Journal Article
• Language: English
• Published: England 01-01-2016
• Subjects: Anti-HIV Agents - chemical synthesis; Anti-HIV Agents - chemistry; Anti-HIV Agents - pharmacology; Cell Line, Tumor; Cell Survival - drug effects; Cyclopropanes - chemical synthesis; Cyclopropanes - chemistry; Cyclopropanes - pharmacology; HIV - drug effects; HIV - enzymology; HIV Reverse Transcriptase - antagonists & inhibitors; HIV Reverse Transcriptase - metabolism; Humans; Indoles - chemical synthesis; Indoles - chemistry; Indoles - pharmacology; Microbial Sensitivity Tests; Molecular Conformation; Organoselenium Compounds - chemistry; Organoselenium Compounds - pharmacology; Reverse Transcriptase Inhibitors - chemical synthesis; Reverse Transcriptase Inhibitors - chemistry; Reverse Transcriptase Inhibitors - pharmacology; Spiro Compounds - chemical synthesis; Spiro Compounds - chemistry; Spiro Compounds - pharmacology; Vinyl Compounds - chemistry; Vinyl Compounds - pharmacology; Virus Replication - drug effects
• DOI: 10.1039/c5ob02451j
• EISSN: 1477-0539

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. Compound showed selective anti-HIV-1 activity thanks to its ability to inhibit the reverse transcriptase.