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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 28, Number 5
BKCSDE 28(5)
May 20, 2007

Title	Synthesis and Characterization of Novel Hydantoins as Potential COX-2 Inhibitors: 1,5-Diarylhydantoins
Author	Hae-Sun Park, Hee-Jeon Choi, Hea-Soon Shin, Sang Kook Lee, Myung-Sook Park*
Keywords	Diarylhydantoins, Diaryl-2-thiohydantoins, Hydantoins, Synthesis, COX-2 inhibitors
Abstract	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 α-anilinophenylacetate 7-15 to 3-alkylhydantoins was carried out in a one-pot reaction using alkyl isocyanate (alkyl isothiocyanate).
Page	751 - 757
Full Text	PDF

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