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Synthesis and characterization of novel hydantoins as potential COX-2 inhibitors: 1,5-diairylhydantoins

Title
Synthesis and characterization of novel hydantoins as potential COX-2 inhibitors: 1,5-diairylhydantoins
Authors
Park, Hae-SunChoi, Hee-JeonShin, Hea-SoonLee, Sang KookPark, Myung-Sook
Ewha Authors
이상국
Issue Date
2007
Journal Title
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
ISSN
0253-2964JCR Link
Citation
vol. 28, no. 5, pp. 751 - 757
Keywords
diarylhydantoinsdiaryl-2-thiohydantoinshydantoinssynthesisCOX-2 inhibitors
Publisher
KOREAN CHEMICAL SOC
Indexed
SCI; SCIE; SCOPUS; KCI WOS scopus
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 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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약학대학 > 약학과 > Journal papers
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