152595-77-2

Basic information

• Product Name: 1-[4-(3-Hydroxy-5-trifluoromethyl-1H-pyrazol-4-ylmethyl)-phenyl]-ethanone
• Synonyms: 1-[4-(3-Hydroxy-5-trifluoromethyl-1H-pyrazol-4-ylmethyl)-phenyl]-ethanone
• CAS NO: 152595-77-2
• Molecular Weight: 284.238
• Mol File: 152595-77-2.mol

Chemical Properties

• CAS DataBase Reference: 1-[4-(3-Hydroxy-5-trifluoromethyl-1H-pyrazol-4-ylmethyl)-phenyl]-ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[4-(3-Hydroxy-5-trifluoromethyl-1H-pyrazol-4-ylmethyl)-phenyl]-ethanone(152595-77-2)
• EPA Substance Registry System: 1-[4-(3-Hydroxy-5-trifluoromethyl-1H-pyrazol-4-ylmethyl)-phenyl]-ethanone(152595-77-2)

Safety Data

• Hazardous Substances Data: 152595-77-2(Hazardous Substances Data)

Upstream product

• 51229-51-7 4-acetylbenzyl bromide 

Relevant articles and documents

New potent antihyperglycemic agents in db/db mice: Synthesis and structure-activity relationship studies of (4-substituted benzyl)(trifluoromethyl)pyrazoles and -pyrazolones

The synthesis, structure-activity relationship (SAR) studies, and antidiabetic characterization of 1,2-dihydro-4-[[4- (methylthio)phenyl]methyl]-5-(trifluoromethyl)-3H-pyrazol-3-one (as the hydroxy tautomer; WAY-123783, 4) are described. Substitution of 4-methylthio, methylsulfinyl, or ethyl to a benzyl group at C4, in combination with trifluoromethyl at C5 of pyrazol-3-one, generated potent antihyperglycemic agents in obese, diabetic db/db mice (16-30% reduction in plasma glucose at 2 mg/kg). The antihyperglycemic effect was associated with a robust glucosuria (>8 g/dL) observed in nondiabetic mice. Chemical trapping of four of the seven possible tautomeric forms of the heterocycle by mono- and dialkylation at the acidic hydrogens provided several additional potent analogs (39-43% reduction at 5 mg/kg) of the lead 4 as well as a dialkylated pair of regioisomers that showed separation of the associated glucosuric effect produced by all of the active analogs in normal mice. Further pharmacological characterization of the lead WAY-123783 (ED50 = 9.85 mg/kg, po in db/db mice), in oral and subcutaneous glucose tolerance tests, indicated that unlike the renal and intestinal glucose absorption inhibitor phlorizin, pyrazolone 4 does not effectively block intestinal glucose absorption. SAR and additional pharmacological data reported herein suggest that WAY-123783 represents a new class of potent antihyperglycemic agents which correct hyperglycemia by selective inhibition of renal tubular glucose reabsorption.

Process for treating hyperglycemia using trifluoromethyl substituted 3H-pyrazol-3-ones

The compound of the formula: STR1 in which the dotted lines represent two sites of unsaturation appropriately located based on the identity of R2, R3 and R4 and, R1 is alkyl, perfluoroalkyl, alkoxy, perfluoroalk