1-methyl-N-[4-(piperidine-1-sulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

• ChemBase ID: 154676
• Molecular Formular: C17H19F3N4O3S
• Molecular Mass: 416.4179696
• Monoisotopic Mass: 416.11299615
• SMILES: Cn1c(cc(n1)C(F)(F)F)C(=O)Nc1ccc(cc1)S(=O)(=O)N1CCCCC1
• Canonical SMILES: O=C(c1cc(nn1C)C(F)(F)F)Nc1ccc(cc1)S(=O)(=O)N1CCCCC1
• InChI: InChI=1S/C17H19F3N4O3S/c1-23-14(11-15(22-23)17(18,19)20)16(25)21-12-5-7-13(8-6-12)28(26,27)24-9-3-2-4-10-24/h5-8,11H,2-4,9-10H2,1H3,(H,21,25)
• InChIKey: OJDLQNVQEAZKSL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-N-[4-(piperidine-1-sulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide
• IUPAC Traditional name: 2-methyl-N-[4-(piperidine-1-sulfonyl)phenyl]-5-(trifluoromethyl)pyrazole-3-carboxamide
• Synonyms: 1-Methyl-N-[4-(1-piperidinylsulfonyl)phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide; CID 16122506; SID 24769845;; AS-136A

Database IDs

• CAS Number: 949898-66-2
• MDL Number: MFCD16875415
• PubChem SID: 162248814
• PubChem CID: 16122506

CALCULATED PROPERTIES

• H Donor: 1
• LogD (pH = 5.5): 2.5804372
• LogD (pH = 7.4): 2.5802593
• Log P: 2.5804396
• Molar Refractivity: 110.0674 cm^3
• Polarizability: 36.553566 Å^3
• Polar Surface Area: 84.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 10.759642
• H Acceptors: 4

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: desiccated
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H19F3N4O3S

DETAILS

Sigma Aldrich - A6486

Application
AS-136A is a small molecule developed as part of the NIH Probes effort. AS-136A is a potent measles virus (MeV) RNA-dependent RNA polymerase (RdRp) inhibitor. AS-136A is very stable, decreases virus titer after 24 hours in physiological conditions, and serves as a positive control in MeV inhibitory assays.
Biochem/physiol Actions
AS-136A is a potent measles virus RdRp inhibitor. Measles virus (MV) is a member of the paramyxovirus family. Ribavirin (R9644) is the only drug available for treatment of paramyxoviruses, and it has limited efficacy against MV. A series of small molecules has been developed to inhibit viral RNA-dependent RNA polymerase (RdRp), a protein vital to infection leading to the development of AS-136A, a very potent RdRp inhibitor. AS-136A has high stability and continues to decrease virus titer after 24 hours in physiologic conditions. AS-136A is now used as a positive control in experiments assaying MV inhibition. This compound is a product of the NIH Probes effort, also known as SID 24769845.