Amflutizole

Amflutizole
Clinical data
ATC code	none;
Identifiers
	IUPAC name 4-Amino-3-[3-(trifluoromethyl)phenyl]-1,2-thiazole-5-carboxylic acid;
CAS Number	82114-19-0 ;
PubChem CID	54833;
ChemSpider	49508 ;
UNII	83N680M457;
KEGG	D02896 ;
ChEMBL	ChEMBL2106558;
CompTox Dashboard (EPA)	DTXSID00868642 ;
Chemical and physical data
Formula	C11H7F3N2O2S
Molar mass	288.24 g·mol−1
3D model (JSmol)	Interactive image;
	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) ; Key:KVMCEGAWQYTFKC-UHFFFAOYSA-N ;
	(verify)

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

Synthesis

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

^ 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.
^ Beck, Gajewski, and Hackler; U.S. patent 4,346,094 (1982 to Eli Lilly and Co).

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[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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