Pharmacological classification and activity evaluation of furan and thiophene amide derivatives applying semi-empirical ab initio molecular modeling methods

Int J Mol Sci. 2012;13(6):6665-6678. doi: 10.3390/ijms13066665. Epub 2012 May 30.

Abstract

Pharmacological and physicochemical classification of the furan and thiophene amide derivatives by multiple regression analysis and partial least square (PLS) based on semi-empirical ab initio molecular modeling studies and high-performance liquid chromatography (HPLC) retention data is proposed. Structural parameters obtained from the PCM (Polarizable Continuum Model) method and the literature values of biological activity (antiproliferative for the A431 cells) expressed as LD(50) of the examined furan and thiophene derivatives was used to search for relationships. It was tested how variable molecular modeling conditions considered together, with or without HPLC retention data, allow evaluation of the structural recognition of furan and thiophene derivatives with respect to their pharmacological properties.

Keywords: HPLC; furan derivatives; molecular modeling; structural analysis; thiophene derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Antineoplastic Agents / chemistry
  • Cell Line, Tumor
  • Chemistry, Pharmaceutical
  • Chromatography
  • Chromatography, High Pressure Liquid
  • Furans / chemistry*
  • Humans
  • Least-Squares Analysis
  • Models, Molecular
  • Molecular Conformation
  • Quantum Theory
  • Regression Analysis
  • Thiophenes / chemistry*
  • Water / chemistry

Substances

  • Amides
  • Antineoplastic Agents
  • Furans
  • Thiophenes
  • Water