ethyl 1-[4-(trichloroprop-2-enamido)phenyl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

• ChemBase ID: 155789
• Molecular Formular: C16H11Cl3F3N3O3
• Molecular Mass: 456.6310496
• Monoisotopic Mass: 454.98180893
• SMILES: CCOC(=O)c1cnn(c1C(F)(F)F)c1ccc(cc1)NC(=O)C(=C(Cl)Cl)Cl
• Canonical SMILES: CCOC(=O)c1cnn(c1C(F)(F)F)c1ccc(cc1)NC(=O)C(=C(Cl)Cl)Cl
• InChI: InChI=1S/C16H11Cl3F3N3O3/c1-2-28-15(27)10-7-23-25(12(10)16(20,21)22)9-5-3-8(4-6-9)24-14(26)11(17)13(18)19/h3-7H,2H2,1H3,(H,24,26)
• InChIKey: RZHGONNSASQOAY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 1-[4-(trichloroprop-2-enamido)phenyl]-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate
• IUPAC Traditional name: ethyl 1-[4-(trichloroprop-2-enamido)phenyl]-5-(trifluoromethyl)pyrazole-4-carboxylate
• Synonyms: Ethyl-1-(4-(2,3,3-trichloroacrylamide)phenyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate; Pyr3

Database IDs

• MDL Number: MFCD00178741
• PubChem SID: 162249927
• PubChem CID: 56964346

CALCULATED PROPERTIES

• Acid pKa: 13.629874
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.3544817
• LogD (pH = 7.4): 4.3544827
• Log P: 4.354483
• Molar Refractivity: 111.7464 cm^3
• Polarizability: 37.19015 Å^3
• Polar Surface Area: 73.22 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: off-white powder

Safety Information

• UN Number: 3077
• Hazard Class: 9
• Packing Group: 3
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C16H11Cl3F3N3O3

DETAILS

Sigma Aldrich - P0032

Biochem/physiol Actions
Pyr3 is a pyrazole compound that potently and selectively antagonizes TRPC3. Pyr3 inhibits TRPC3 by binding to the extracellular side of the receptor, resulting in suppression of B cell activation and cardiac hypertrophy.Members of the canonical transient receptor potential (TRPC) channel family are ion channels which conduct Ca+2 and are activated by membrane receptor-mediated stimulation of phospholipase C (PLC) activity. However, TRPC3 and other family members are also activated by membrane-independent diacylglycerol (DAG). BTP1 and BTP2 are pyrazoles that block TRPC channels, but they are not specific for TRPC subtypes. This channel is implicated in various processes, including B cell receptor (BCR)-mediated Ca+2 oscillations, activation of nuclear factor of activated T cells (NFAT), and promotion of cardiac hypertrophy.
Pyr3 is a selectively inhibitor of TRPC3. It acts by binding to the extracellular side of the receptor, resulting in suppression of B cell activation and cardiac hypertrophy.Members of the canonical transient receptor potential (TRPC) channel family are Ca2+ ion channels that are activated by membrane receptor-mediated stimulation of phospholipase C (PLC). However, TRPC3 and other family members are also activated by membrane-independent diacylglycerol (DAG). This channel is implicated in various processes, including B cell receptor (BCR)-mediated Ca2+ oscillations, activation of nuclear factor of activated T cells (NFAT), and promotion of cardiac hypertrophy.