Synthesis and antimicrobial evaluation of some new thiazole, thiazolidinone and thiazoline derivatives starting from 1-chloro-3,4-dihydronaphthalene-2-carboxaldehyde

Eur J Med Chem. 2007 Jul;42(7):948-54. doi: 10.1016/j.ejmech.2006.12.025. Epub 2007 Jan 13.

Abstract

The thiosemicarbazones (3 and 6) and N-arylidene cyanoacetohydrazide (12) were prepared and used as key intermediates for the synthesis of 4-thiazolidinones (4, 5, 7-9), thiazoles (10a,b and 11a-d) and thiazoline (13) derivatives. Treatment of 13 with a mixture of triethylorthoformate and acetic anhydride afforded thiazolo[5,4-d]pyrimidinone derivative (14). The newly synthesized compounds were characterized by IR, (1)H NMR and mass spectral studies. Representative compounds of the synthesized products were tested and evaluated as antimicrobial agents.

MeSH terms

  • Aldehydes / chemistry*
  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / pharmacology
  • Bacteria / drug effects
  • Dose-Response Relationship, Drug
  • Fungi / drug effects
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Thiazoles / chemical synthesis*
  • Thiazoles / pharmacology

Substances

  • 1-chloro-3,4-dihydronaphthalene-2-carboxaldehyde
  • Aldehydes
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Naphthalenes
  • Thiazoles