Amflutizole

Amflutizole is a xanthine oxidase inhibitor[1] used for the treatment of gout.

Amflutizole
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 4-Amino-3-[3-(trifluoromethyl)phenyl]-1,2-thiazole-5-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC11H7F3N2O2S
Molar mass288.24 g·mol−1
3D model (JSmol)
SMILES
  • FC(F)(F)c1cccc(c1)c2nsc(c2N)C(=O)O
InChI
  • InChI=1S/C11H7F3N2O2S/c12-11(13,14)6-3-1-2-5(4-6)8-7(15)9(10(17)18)19-16-8/h1-4H,15H2,(H,17,18) Y
  • Key:KVMCEGAWQYTFKC-UHFFFAOYSA-N Y
  (verify)

Synthesis
Patent:[2]

The tosyl oxime of the meta-trifluromethyl benzoic acid acid cyanide is the reactant, CID:53648583 (1). This is cross reacted with Ethyl thioglycolate [623-51-8] (2) 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 (3). This adds to the cyano group; protonation then goes on to form the imine (4), tautomerization of which gives the corresponding amino form (5). Finally, saponification of the ester thus affords amflutizole (6).

References
  1. O'Regan MH, Smith-Barbour M, Perkins LM, Cao X, Phillis JW (October 1994). "The effect of amflutizole, a xanthine oxidase inhibitor, on ischemia-evoked purine release and free radical formation in the rat cerebral cortex". Neuropharmacology. 33 (10): 1197–201. doi:10.1016/S0028-3908(05)80010-3. PMID 7862255. S2CID 37262919.
  2. Beck, Gajewski, and Hackler; U.S. Patent 4,346,094 (1982 to Eli Lilly and Co).
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