잠재적 COX-2의 억제작용이 있는 1,5-Diarylhtdantoin 유도체의 합성 = Synthesis of Potential COX-2 Inhibitory 1,5-Diarydantoin Derivatives

다국어 초록 (Multilingual Abstract)

For the development of new COX-2 inhibitors, 1,5-diarylhydantoins 5a~5c and 1,5-diaryl-2-thiohydantoin 6a~6c were synthesized from commercially available phenylacetic acids through esterification, bromination, C-N bond formation and cyclization. Esters 2a~c were efficiently synthesized from the starting materials la~c by refluxing in absolute methanol for 3 hours with catalytic concentrated sulfuric acid. Bromination of 2a~c was carried out with use of N-bomosuccinimide at rt in dichloromethane. The bromine of 3a~c was substituted with aniline in ethanol or N,N-dimethylformamide to provide 4a~c. Hydantoins and 2-thiohydantoins were synthesized from 4a~c by treatment of potassium isocyanate or potassium thiocyanate in dil-ethanol with triethylamine.