Facile one-pot synthesis of novel dispirooxindole-pyrrolidine derivatives and their antimicrobial and anticancer activity against A549 human lung adenocarcinoma cancer cell line

Bioorg Med Chem Lett. 2013 Mar 15;23(6):1839-45. doi: 10.1016/j.bmcl.2013.01.023. Epub 2013 Jan 22.

Abstract

Novel dispirooxindole-pyrrolidine derivatives have been synthesized through 1,3-dipolar cycloaddition of an azomethine ylide generated from isatin and sarcosine with the dipolarophile 3-(1H-indol-3-yl)-3-oxo-2-(2-oxoindolin-3-ylidene)propanenitrile, and also spiro compound of acenaphthenequinone obtained by the same optimized reaction condition. Synthesized compounds were evaluated for their antimicrobial activity and all the compounds shown significant activity. Anticancer activity was evaluated against A549 human lung adenocarcinoma cancer cell lines. Compounds 7b, 7g, 7i and 7r exhibit very good anticancer activity 62.96%, 62.03%, 67.67% and 60.22%, respectively, at the dose of 200μg/mL and compound 7i shows IC50 value in 50μg/mL.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenocarcinoma / drug therapy
  • Adenocarcinoma of Lung
  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / therapeutic use
  • Antineoplastic Agents / toxicity
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Crystallography, X-Ray
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Humans
  • Indoles / chemistry*
  • Indoles / pharmacology
  • Indoles / toxicity
  • Lung Neoplasms / drug therapy
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Oxindoles
  • Pyrrolidines / chemistry*
  • Pyrrolidines / pharmacology
  • Pyrrolidines / toxicity
  • Spiro Compounds / chemistry
  • Structure-Activity Relationship

Substances

  • Anti-Infective Agents
  • Antineoplastic Agents
  • Indoles
  • Oxindoles
  • Pyrrolidines
  • Spiro Compounds
  • 2-oxindole
  • pyrrolidine