Efficient microwave-assisted synthesis and antitumor activity of novel 4,4'-methylenebis[2-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)phenols]

Eur J Med Chem. 2011 Jun;46(6):2436-40. doi: 10.1016/j.ejmech.2011.03.028. Epub 2011 Mar 23.

Abstract

Two new series of 4,4'-methylenebis[2-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)phenols] 4 and methylenebis-2-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-4,1-phenylene diacetates 5 have been efficiently prepared starting from the commercially available salicylaldehyde and where the key step corresponded to the microwave-assisted reaction of intermediates 3,3'-[methylenebis(6-hydroxy-3,1-phenylene)]bis(1-arylprop-2-en-1-ones) 3 with hydrazine hydrate or acetic acid/hydrazine hydrate respectively. Three unacetylated compounds type 4 presented interesting antitumor activities against a wide range of tumor cell lines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Design
  • Drug Screening Assays, Antitumor
  • Humans
  • Microwaves*
  • Molecular Structure
  • Phenols / chemical synthesis
  • Phenols / chemistry
  • Phenols / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Phenols