Synthesis and Characterization of Novel Hydantoins as Potential COX-2 Inhibitors: 1,5-Diarylhydantoins

Bulletin of the Korean chemical society

Hea-Soon Shin¹  Sang Kook Lee¹  Hae-Sun Park¹  Myung-Sook Park¹  Hee-Jeon Choi¹ 

关键词: Diarylhydantoins;    Diaryl-2-thiohydantoins;    Hydantoins;    Synthesis;    COX-2 inhibitors;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

To develop new COX-2 inhibitors, 1,5-diarylhydantoins and 1,5-diaryl-2-thiohydantoins were synthesized from phenylacetic acids by esterification, bromination, C-N bond formation and cyclization. Esters 1-3 were efficiently synthesized from the starting materials by reflux in absolute methanol for 3 h containing concentrated sulfuric acid as catalyst. Bromination was carried out with N-bromosuccinimide at rt in dichloromethane. Bromides 4-6 were reacted with aniline, p-anisidine, sulfanilamide in ethanol (or N,N-dimethylformamide) to provide the amines 7-15. Hydantoins and 2-thiohydantoins 16-46 were synthesized from amines 7-15 by treating them with potassium isocyanate (or potassium thiocyanate) and triethylamine. The synthetic process from alkyl �?-anilinophenylacetate 7-15 to 3-alkylhydantoins was carried out in a one-pot reaction using alkyl isocyanate (alkyl isothiocyanate).

【 授权许可】

Unknown