Synthesis and 2D-QSAR Study of Active Benzofuran-Based Vasodilators

Molecules. 2017 Oct 26;22(11):1820. doi: 10.3390/molecules22111820.

Abstract

A new series of 2-alkyloxy-pyridine-3-carbonitrile-benzofuran hybrids (4a-x) was synthesized. All the new derivatives were examined via the standard technique for their vasodilation activity. Some of the investigated compounds exhibited a remarkable activity, with compounds 4w, 4e, 4r, 4s, 4f and 4g believed to be the most active hits in this study with IC50 values 0.223, 0.253, 0.254, 0.268, 0.267 and 0.275 mM, respectively, compared with amiodarone hydrochloride, the reference standard used (IC50 = 0.300 mM). CODESSA PRO was employed to obtain a statistically significant 2-Dimensional Quantitative Structure Activity Relationship (2D-QSAR) model describing the bioactivity of the newly synthesized analogs (N = 24, n = 4, R² = 0.816, R²cvOO = 0.731, R²cvMO = 0.772, F = 21.103, s² = 6.191 × 10-8).

Keywords: 2D-QSAR; amiodarone hydrochloride; benzofuran; vasodilation activity.

MeSH terms

  • Animals
  • Aorta / drug effects
  • Benzofurans / chemical synthesis
  • Benzofurans / chemistry*
  • Benzofurans / pharmacology
  • Chemistry Techniques, Synthetic*
  • Inhibitory Concentration 50
  • Mice
  • Molecular Structure
  • Quantitative Structure-Activity Relationship*
  • Rats
  • Vasodilator Agents / chemical synthesis
  • Vasodilator Agents / chemistry*
  • Vasodilator Agents / pharmacology

Substances

  • Benzofurans
  • Vasodilator Agents
  • benzofuran