X-ray Single Crystal Structure, DFT Calculations and Biological Activity of 2-(3-Methyl-5-(pyridin-2'-yl)-1H-pyrazol-1-yl) Ethanol

Molecules. 2016 Aug 5;21(8):1020. doi: 10.3390/molecules21081020.

Abstract

A pyridylpyrazole bearing a hydroxyethyl substituent group has been synthesized by condensation of (Z)-4-hydroxy-4-(pyridin-2-yl)but-3-en-2-one with 2-hydroxyethylhydrazine. The compound was well characterized and its structure confirmed by single crystal X-ray diffraction. Density functional calculations have been performed using DFT method with 6-31G* basis set. The HOMO-LUMO energy gap, binding energies and electron deformation densities are calculated at the DFT (BLYP, PW91, PWC) level. The electrophilic f(-) and nucleophilic f(+) Fukui functions and also the electrophilic and nucleophilic Parr functions are well adapted to find the electrophile and nucleophile centers in the molecule. The title compound has been tested for its DPPH radical scavenging activity which is involved in aging processes, anti-inflammatory, anticancer and wound healing activity. Compound is also found with a significant antioxidant activity, probably due to the ability to donate a hydrogen atom to the DPPH radical.

Keywords: DFT calculations; Fukui functions; Parr functions; biological activity; pyridylpyrazole; reactivity indices; single-crystal.

MeSH terms

  • Crystallography, X-Ray
  • Ethanol / chemistry*
  • Ethanol / pharmacology
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Structure
  • Oxidative Stress / drug effects
  • Pyridines / chemistry*
  • Pyridines / pharmacology
  • Static Electricity

Substances

  • Pyridines
  • Ethanol