InCl3-catalysed synthesis of 2-aryl quinazolin-4(3H)-ones and 5-aryl pyrazolo[4,3-d]pyrimidin-7(6H)-ones and their evaluation as potential anticancer agents

Bioorg Med Chem Lett. 2012 Aug 1;22(15):5063-6. doi: 10.1016/j.bmcl.2012.06.003. Epub 2012 Jun 13.

Abstract

A convenient and practical methodology for the synthesis of 2-aryl quinazolin-4(3H)-ones by the condensation of o-aminobenzamides with aromatic aldehydes under mild conditions using catalytic InCl(3) with good yields and high selectivities. This method has been extended for the synthesis of 5-aryl pyrazolo[4,3-d]pyrimidin-7(6H)-ones which have potential applications in medicinal chemistry. Many of these compounds were evaluated for their anti-proliferative properties in vitro against four cancer cell lines and several compounds were found to be active. Further in vitro studies indicated that inhibition of sirtuins could be the possible mechanism of action of these molecules.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / toxicity
  • Apoptosis / drug effects
  • Binding Sites
  • Catalysis
  • Catalytic Domain
  • Cell Line, Tumor
  • Computer Simulation
  • Drug Screening Assays, Antitumor
  • Humans
  • Indium / chemistry*
  • K562 Cells
  • Pyrimidinones / chemical synthesis
  • Pyrimidinones / chemistry*
  • Pyrimidinones / toxicity
  • Quinazolinones / chemical synthesis
  • Quinazolinones / chemistry*
  • Quinazolinones / toxicity
  • Sirtuin 1 / chemistry
  • Sirtuin 1 / metabolism

Substances

  • Antineoplastic Agents
  • Pyrimidinones
  • Quinazolinones
  • Indium
  • indium trichloride
  • SIRT1 protein, human
  • Sirtuin 1