Synthesis, structure, and bioactivity of N'-substituted benzylidene-3,4,5-trimethoxybenzohydrazide and 3-acetyl-2-substituted phenyl-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole derivatives

Bioorg Med Chem Lett. 2006 Oct 1;16(19):5036-40. doi: 10.1016/j.bmcl.2006.07.048. Epub 2006 Jul 28.

Abstract

Some 3-acetyl-2-substituted phenyl-5-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole derivatives were synthesized by cyclization reaction of N'-substituted benzylidene-3,4,5-trimethoxybenzohydrazide in acetic anhydride. Their structures were verified by elemental analysis, IR, (1)H NMR, and (13)C NMR. Compound 3i was provided with X-ray crystallographic data. The compounds were evaluated for their antiproliferative activities against some cancer cells in vitro by MTT method. Among them, 2a, 2b, 2c, 2f, 3l, and 3m were highly effective against PC3 cells and 2a, 2c, and 2f showed moderate activities against Bcap37 and BGC823 cells. The IC(50) values of high active compounds 2a, 2b, 2c, 2f, 3l, and 3m against PC3 cells were 0.2, 1.8, 0.2, 1.2, 1.7, and 0.3muM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Benzylidene Compounds / chemical synthesis
  • Benzylidene Compounds / chemistry*
  • Benzylidene Compounds / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Humans
  • Inhibitory Concentration 50
  • Molecular Structure
  • Neoplasms / drug therapy
  • Neoplasms / pathology
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / chemistry*
  • Oxadiazoles / pharmacology*
  • Prohibitins
  • Spectrum Analysis
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Benzylidene Compounds
  • Oxadiazoles
  • PHB2 protein, human
  • Prohibitins