Synthesis, enantioseparation and pharmacological activity of 4-aryl-7,7-dimethyl-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thiones

Yarim M., Sarac S., Ertan M., Kilic F. S., Erol K.

ARZNEIMITTEL-FORSCHUNG-DRUG RESEARCH, vol.52, no.1, pp.27-33, 2002 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 52 Issue: 1
  • Publication Date: 2002
  • Doi Number: 10.1055/s-0031-1299852
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.27-33
  • Keywords: calcium antagonists, 1,2,3,4,5,6,7,8-octahydroquinazoline-2-thiones, calcium antagonist activity, enantioseparation, synthesis, CALCIUM-CHANNEL BLOCKERS, CHIRAL STATIONARY PHASES, PERFORMANCE LIQUID-CHROMATOGRAPHY, ACID-ESTERS, ANTIHYPERTENSIVE AGENTS, OPTICAL RESOLUTION, MODULATORS, AMYLOSE, POTENT, ANTAGONISTS
  • Eskisehir Osmangazi University Affiliated: Yes


4-Aryl-7,7-dimethyl-5-oxo-1,2,3,4,5,6,7,8-octahydroquinazoline-2-thione derivatives (1-8) have been prepared by modified Biginelli reaction from 5,5-dimethyl-1,3-cyclohexanedione, the aromatic aldehydes and thiourea. The structures of the compounds were confirmed by spectroscopic and elemental analysis. Racemic compounds were resolved into their enantiomers by HPLC using an amylose tris-(3,5-dimethylphenylcarbamate) chiral stationary phase in the normal phase mode. The calcium antagonist activities of the compounds were determined by the tests performed on isolated rat ileum and lamb carotid artery. Compounds 2, 3, 4 and 6 were the most active compounds on isolated rat ileum. Compounds 2 and 3 were significantly active on lamb carotid artery.