Synthesis and antitumor activity of 5-(5-halogenated-2-oxo-1H-pyrrolo[2,3-b]pyridin-(3Z)-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamides

Bioorg Med Chem Lett. 2015 Jul 15;25(14):2782-7. doi: 10.1016/j.bmcl.2015.05.017. Epub 2015 May 15.

Abstract

We report herein the design and synthesis of a series of novel 5-halogenated-7-azaindolin-2-one derivatives containing a 2,4-dimethylpyrrole moiety. Nine target compounds with ⩾70% inhibition against MCF-7 at 30 μM were further evaluated for their in vitro antitumor activity against seven human cancer cell lines by SRB assay. Results reveal that some compounds have potent antitumor activity, and the most active 13c7 (IC50s: 4.49-15.39 μM) was found to be more active than Sunitinib (IC50s: 4.70->30 μM) against all of the tested cancer cell lines.

Keywords: 7-Azaindolin-2-ones; Antitumor activity; Synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry*
  • Amides / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Drug Screening Assays, Antitumor
  • Humans
  • Indoles
  • MCF-7 Cells
  • Pyrimidines / chemistry
  • Pyrroles / chemistry
  • Structure-Activity Relationship
  • Sunitinib

Substances

  • 2,4-dimethylpyrrole
  • Amides
  • Antineoplastic Agents
  • Indoles
  • Pyrimidines
  • Pyrroles
  • pyrrolopyrimidine
  • Sunitinib