Synthesis of 4H-chromene, coumarin, 12H-chromeno[2,3-d]pyrimidine derivatives and some of their antimicrobial and cytotoxicity activities

Eur J Med Chem. 2011 Feb;46(2):765-72. doi: 10.1016/j.ejmech.2010.12.015. Epub 2010 Dec 21.

Abstract

Condensation of 3-N,N-diethylaminophenol (1) with α-cyanocinnamonitriles (2a-c) and ethyl α-cyanocinnamates (2d-f) provided compounds 3a-f and 4a-c. 12H-Chromeno[2,3-d]pyrimidine derivatives 6, 11-13 and 16 were obtained by treatment of 4H-chromene compounds (3) with different electrophiles followed by nucleophilic reagents. Structures of these compounds were established on the basis of IR, UV, 1H NMR, 13C NMR and MS data. Some of the new compounds were evaluated for antimicrobial and cytotoxicity activities.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Bacteria / drug effects
  • Benzopyrans / chemical synthesis
  • Benzopyrans / chemistry
  • Benzopyrans / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Coumarins / chemical synthesis
  • Coumarins / chemistry
  • Coumarins / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Fungi / drug effects
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Pyrimidines / chemical synthesis
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 12H-chromeno(2,3-d)pyrimidine
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Antineoplastic Agents
  • Benzopyrans
  • Coumarins
  • Pyrimidines
  • coumarin