Synthesis of novel antiproliferative hybrid bis-(3-indolyl)methane phosphonate derivatives

Eur J Med Chem. 2018 Oct 5:158:874-883. doi: 10.1016/j.ejmech.2018.09.011. Epub 2018 Sep 15.

Abstract

An efficient synthetic methodology for the preparation of phosphorus substituted bis-(3-indolyl)methane through a double nucleophilic addition of indole derivatives to an in situ generated α-iminophosphonate is reported. In addition, bis-(3-indolyl)methane substrates showed in vitro cytotoxicity, inhibiting the growth of carcinoma human tumor cell lines A549 (carcinomic human alveolar basal epithelial cell) and SKOV03 (human ovarian carcinoma).

Keywords: Antiproliferative effect; Bis-(3-indolyl)methanes (BIMs); Indole; Phosphonate.

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects*
  • Humans
  • Indoles / chemical synthesis
  • Indoles / chemistry*
  • Indoles / pharmacology*
  • Methane / analogs & derivatives*
  • Methane / chemical synthesis
  • Methane / pharmacology*
  • Neoplasms / drug therapy
  • Organophosphonates / chemical synthesis
  • Organophosphonates / chemistry
  • Organophosphonates / pharmacology

Substances

  • Antineoplastic Agents
  • Indoles
  • Organophosphonates
  • Methane