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

Org Biomol Chem. 2016 Feb 14;14(6):2015-24. doi: 10.1039/c5ob02451j.

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

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 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

Substances

  • Anti-HIV Agents
  • Cyclopropanes
  • Indoles
  • Organoselenium Compounds
  • Reverse Transcriptase Inhibitors
  • Spiro Compounds
  • Vinyl Compounds
  • HIV Reverse Transcriptase