Amflutizole
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Systematic (IUPAC) name | |
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4-amino-3-[3-(trifluoromethyl)phenyl]-1,2-thiazole-5-carboxylic acid | |
Clinical data | |
Identifiers | |
82114-19-0 ![]() | |
None | |
PubChem | CID 192344 |
ChemSpider |
49508 ![]() |
UNII |
83N680M457 ![]() |
KEGG |
D02896 ![]() |
ChEMBL | CHEMBL2106558 |
Chemical data | |
Formula | C11H7F3N2O2S |
288.2 g/mol | |
SMILES
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Amflutizole is a xanthine oxidase inhibitor used for the treatment of gout.
Synthesis
The tosyl oxime of the meta-trifluromethyl benzoic acid acid cyanide is the reactamt. This is cross reacted with ethyl 2-mercaptoacetate in the presence of a base; displacement of the tosylate by mercaptide leads to the formation of the heterocyclic N–S bond. This intermediate compound is then converted to the carbanion by a second equivalent of base. This adds to the cyano group; protonation then goes on to form the imine, tautomerization of which gives the corresponding amino form. Finally, saponification of the ester thus affords amflutizole as the product.[1]