New nicotinic acid-based 3,5-diphenylpyrazoles: design, synthesis and antihyperlipidemic activity with potential NPC1L1 inhibitory activity

Mol Divers. 2021 May;25(2):673-686. doi: 10.1007/s11030-020-10039-9. Epub 2020 Feb 17.

Abstract

Nicotinic acid hydrazide was incorporated into new 4,5-dihydro-5-hydroxy-3,5-diphenylpyrazol-1-yl derivatives. Compounds 6a-h were synthesized, and their antihyperlipidemic activity was evaluated in high cholesterol diet-fed rat model. Compounds 6e, 6f were found to decrease the levels of serum total cholesterol by 14-19% compared to control group. Total triglycerides were also reduced by 24-28% and LDL cholesterol by 16%. As expected from parent niacin, compounds 6e and 6f caused an elevation of HDL cholesterol by 33-41%. Docking study supported the ability of designed compounds to block NPC1L1 active site in a manner similar to that observed with ezetimibe.

Keywords: 3,5-diphenylpyrazoles; Antihyperlipidemic; Docking; NPC1L1.

MeSH terms

  • Animals
  • Cholesterol / blood
  • Drug Design
  • Hydrazines / chemistry
  • Hydrazines / therapeutic use*
  • Hyperlipidemias / blood
  • Hyperlipidemias / drug therapy*
  • Hypolipidemic Agents / chemistry
  • Hypolipidemic Agents / therapeutic use*
  • Male
  • Membrane Transport Proteins / chemistry
  • Molecular Docking Simulation
  • Nicotinic Acids / chemistry
  • Nicotinic Acids / therapeutic use*
  • Pyrazoles / chemistry
  • Pyrazoles / therapeutic use*
  • Rats
  • Rats, Wistar
  • Triglycerides / blood

Substances

  • Hydrazines
  • Hypolipidemic Agents
  • Membrane Transport Proteins
  • NPC1L1 protein, human
  • Nicotinic Acids
  • Pyrazoles
  • Triglycerides
  • Cholesterol
  • nicotinic acid hydrazide