Synthesis and quantitative structure-activity relationships study for phenylpropenamide derivatives as inhibitors of hepatitis B virus replication

Eur J Med Chem. 2015 Jun 24:99:82-91. doi: 10.1016/j.ejmech.2015.05.032. Epub 2015 May 28.

Abstract

A series of new phenylpropenamide derivatives containing different substituents was synthesized, characterized and evaluated for their anti-hepatitis B virus (HBV) activities. The quantitative structure-activity relationships (QSAR) of phenylpropenamide compound have been studied. The 2D-QSAR models, based on DFT and multiple linear regression analysis methods, revealed that higher values of total energy (TE) and lower entropy (S(ө)) enhanced the anti-HBV activities of the phenylpropenamide molecules. Predictive 3D-QSAR models were established using SYBYL multifit molecular alignment rule. The optimum models were all statistically significant with cross-validated and conventional coefficients, indicating that they were reliable enough for activity prediction.

Keywords: DFT; Hepatitis B; Phenylpropenamide; QSAR.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Amides / pharmacology*
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Chemistry Techniques, Synthetic
  • Drug Design*
  • Hepatitis B virus / drug effects*
  • Hepatitis B virus / physiology*
  • Models, Molecular
  • Molecular Conformation
  • Quantitative Structure-Activity Relationship*
  • Virus Replication / drug effects*

Substances

  • Amides
  • Antiviral Agents