Design, synthesis and biological evaluation of piperazinyl-β-carbolinederivatives as anti-leishmanial agents

Eur J Med Chem. 2018 Apr 25:150:559-566. doi: 10.1016/j.ejmech.2018.03.022. Epub 2018 Mar 8.

Abstract

Molecular hybridization is a ligand based drug design approach is well known recent medicinal chemistry to design anti-parasitic agents. In the present study, we have designed a series of (1-phenyl-9H-pyrido [3,4-b]indol-3-yl) (4-phenylpiperazin-1-yl)methanone derivatives using molecular hybridization approach. Designed analogues were evaluated for cytotoxicity and inhibition activity against Leishmania infantum and Leishmania donovani. Among these reported analogues 7b, 7d, 7e, 7f and 7m displayed potent inhibition of both L. infantum and L. donovani. Compounds 7i and 7k exhibited selective potent inhibition of L. donovani. Especially, compounds 7e and 7k showed most potent anti-leishmanial activity against L. infantum and L. donovani respectively. Anti-leishmanial activity of these compounds is comparable with standard drugs miltefosine and pentamidine. SAR studies revealed that, electron donating group substitution on phenyl ring recommended for potent anti-leishmanial activity.

Keywords: Anti-leishmanial activity; Leishmania donovani; Leishmania infantum; Molecular hybridization; β-carboline.

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Antiprotozoal Agents / chemical synthesis
  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / pharmacology*
  • Carbolines / chemical synthesis
  • Carbolines / chemistry
  • Carbolines / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Humans
  • Leishmania donovani / cytology
  • Leishmania donovani / drug effects*
  • Leishmania infantum / cytology
  • Leishmania infantum / drug effects*
  • Molecular Structure
  • Parasitic Sensitivity Tests
  • Piperazines / chemical synthesis
  • Piperazines / chemistry
  • Piperazines / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Antiprotozoal Agents
  • Carbolines
  • Piperazines