Antimicrobial and antileishmanial studies of novel (2E)-3-(2-chloro-6-methyl/methoxyquinolin-3-yl)-1-(aryl)prop-2-en-1-ones

Chem Pharm Bull (Tokyo). 2010 Mar;58(3):301-6. doi: 10.1248/cpb.58.301.

Abstract

Thirty eight heterocyclic chalcones were synthesized by condensing formylquinolines with diverse methyl arylketones. The target compounds were characterized by spectroscopic techniques (NMR, IR, MS) and elemental analysis. The X-ray crystallographic study of (2E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)prop-2-en-1-one (1p) was also performed for the structure confirmation. The title compounds were screened for anti-microbial and antileishmanial activities. The compounds 1c-e, 1g, 1j-m, 1p, 1r-s, 2g, 2j-p, and 2r-s were found potentially active antileishmanial agents, while 1f-i, 1l, 1o-p, 2f-i, 2l, and 2o-p showed remarkable antibacterial activity. Only compounds 1g and 2g-h exhibited significant antifungal activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology*
  • Antiprotozoal Agents / chemical synthesis
  • Antiprotozoal Agents / chemistry
  • Antiprotozoal Agents / pharmacology*
  • Crystallography, X-Ray
  • Dioxins / chemical synthesis
  • Dioxins / chemistry
  • Dioxins / pharmacology*
  • Escherichia coli / drug effects*
  • Leishmania major / drug effects*
  • Microbial Sensitivity Tests
  • Micrococcus luteus / drug effects*
  • Models, Molecular
  • Molecular Conformation
  • Parasitic Sensitivity Tests
  • Quinolines / chemical synthesis
  • Quinolines / chemistry
  • Quinolines / pharmacology*
  • Staphylococcus aureus / drug effects*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Anti-Infective Agents
  • Antiprotozoal Agents
  • Dioxins
  • Quinolines