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Synthesis and characterization of novel hydantoins as potential COX-2 inhibitors: 1,5-diairylhydantoins
- Synthesis and characterization of novel hydantoins as potential COX-2 inhibitors: 1,5-diairylhydantoins
- Park, Hae-Sun; Choi, Hee-Jeon; Shin, Hea-Soon; Lee, Sang Kook; Park, Myung-Sook
- Ewha Authors
- Issue Date
- Journal Title
- BULLETIN OF THE KOREAN CHEMICAL SOCIETY
- BULLETIN OF THE KOREAN CHEMICAL SOCIETY vol. 28, no. 5, pp. 751 - 757
- diarylhydantoins; diaryl-2-thiohydantoins; hydantoins; synthesis; COX-2 inhibitors
- KOREAN CHEMICAL SOC
- SCIE; SCOPUS; KCI
- Document Type
- 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 NN-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 alpha-anilinophenylacetate 7-15 to 3-alkylhydantoins was carried out in a one-pot reaction using alkyl isocyanate (alkyl isothiocyanate).
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