Microwave-assisted synthesis of pyrimido[4,5-b][1,6]naphthyridin-4(3H)-ones with potential antitumor activity

Eur J Med Chem. 2013 Feb:60:1-9. doi: 10.1016/j.ejmech.2012.11.037. Epub 2012 Dec 4.

Abstract

The 6,7,8,9-tetrahydropyrimido[4,5-b][1,6]naphthyridin-4(3H,5H,10H)-ones 4,5a-g and their oxidized forms 6,7a-g were obtained from the catalyst-free reaction of 6-amino-2-methylthiopyrimidin-4(3H)-one 3 and (E)-3,5-bis(benzylidene)-1-alkyl-4-piperidones 1,2a-g under Microwave irradiation and their subsequent oxidation process with p-chloranil. Eighteen of the new compounds were evaluated in the US National Cancer Institute (NCI), where compound 4g presented a remarkable activity against 57 cancer cell lines, with the most important GI(50) values ranging from 1.48 to 9.92 μM from in vitro assays.

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 Screening Assays, Antitumor
  • Humans
  • Microwaves*
  • Molecular Structure
  • Naphthyridines / chemical synthesis
  • Naphthyridines / chemistry
  • Naphthyridines / pharmacology*
  • Pyrimidinones / chemical synthesis
  • Pyrimidinones / chemistry
  • Pyrimidinones / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Naphthyridines
  • Pyrimidinones