Fanetizole

Fanetizole

Pharmacokinetic data
Protein binding	%
Identifiers
IUPAC name 4-Phenyl-N-(2-phenylethyl)-1,3-thiazol-2-amine
CAS Number	79069-94-6
PubChem CID	54339
ChemSpider	49083
UNII	BH48F620JA
CompTox Dashboard (EPA)	DTXSID9048695
Chemical and physical data
Formula	C17H16N2S
Molar mass	280.39 g·mol^−1
3D model (JSmol)	Interactive image
SMILES n1c(csc1NCCc2ccccc2)c3ccccc3
InChI InChI=1S/C17H16N2S/c1-3-7-14(8-4-1)11-12-18-17-19-16(13-20-17)15-9-5-2-6-10-15/h1-10,13H,11-12H2,(H,18,19) Key:WEEYMMXMBFJUAI-UHFFFAOYSA-N
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Fanetizole shows immunoregulating activity.

Synthesis

Thioureas serve as a convenient starting material for 2-aminothiazoles.

Fanetizole synthesis:[1]

Reaction of β-phenethylamine with ammonium isothiocyanate gives the thiourea (2) Treatment of that product with phenacyl bromide thus affords the thiazole product.

References

1. Lombardino, J. G.; 1981, U.S. Patent 4,307,106