Design, synthesis and 3D-QSAR of beta-carboline derivatives as potent antitumor agents

Eur J Med Chem. 2010 Jun;45(6):2503-15. doi: 10.1016/j.ejmech.2010.02.036. Epub 2010 Feb 19.

Abstract

In a continuing effort to develop novel beta-carbolines endowed with better pharmacological profiles, a series of beta-carboline derivatives were designed and synthesized based on the previously developed SARs. Cytotoxicities in vitro of these compounds against a panel of human tumor cell lines were also investigated. The results demonstrated that the N2-benzylated beta-carbolinium bromides 56-60 represented the most potent compounds with IC50 values lower than 10 microM. The application of 3D-QSAR to these compounds explored the structural basis for their biological activities. CoMFA (q2=0.513, r2=0.862) and CoMSIA (q2=0.503, r2=0.831) models were developed for a set of 47 beta-carbolines. The results indicated that the antitumor pharmacophore of these molecules were marked at position-1, -2, -3, -7 and -9 of beta-carboline ring.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Carbolines / chemistry*
  • Carbolines / pharmacology*
  • Cell Line, Tumor
  • Drug Design*
  • Humans
  • Inhibitory Concentration 50
  • Models, Molecular
  • Molecular Conformation
  • Quantitative Structure-Activity Relationship*

Substances

  • Antineoplastic Agents
  • Carbolines