5-cyclopropyl-2-{1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}pyrimidin-4-amine

• ChemBase ID: 154430
• Molecular Formular: C20H17FN6
• Molecular Mass: 360.3875832
• Monoisotopic Mass: 360.14987279
• SMILES: c1ccc(c(c1)Cn1c2c(cccn2)c(n1)c1ncc(c(n1)N)C1CC1)F
• Canonical SMILES: Fc1ccccc1Cn1nc(c2c1nccc2)c1ncc(c(n1)N)C1CC1
• InChI: InChI=1S/C20H17FN6/c21-16-6-2-1-4-13(16)11-27-20-14(5-3-9-23-20)17(26-27)19-24-10-15(12-7-8-12)18(22)25-19/h1-6,9-10,12H,7-8,11H2,(H2,22,24,25)
• InChIKey: ATOAHNRJAXSBOR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-cyclopropyl-2-{1-[(2-fluorophenyl)methyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}pyrimidin-4-amine
• IUPAC Traditional name: 5-cyclopropyl-2-{1-[(2-fluorophenyl)methyl]pyrazolo[3,4-b]pyridin-3-yl}pyrimidin-4-amine
• Synonyms: 3-(4-Amino-5-cyclopropylpyrimidin-2-yl)-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine; BAY 41-2272

Database IDs

• MDL Number: MFCD06411391
• PubChem SID: 162248569; 24892096
• PubChem CID: 9798973

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.8192341
• LogD (pH = 7.4): 3.8193479
• Log P: 3.8193493
• Molar Refractivity: 123.0197 cm^3
• Polarizability: 38.444714 Å^3
• Polar Surface Area: 82.51 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble26 mg/mL at 60 °C
• Apperance: white powder
• Melting Point: 210.5-211.4 °C

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C20H17FN6

DETAILS

Sigma Aldrich - B8810

Biochem/physiol Actions
BAY 41-2272 is an activator of soluble guanylate cyclase at a novel, NO-independent regulatory site. BAY 41-2272 is the first product that stimulates sGC through a non-NO mechanism. BAY 41-2272 inhibits platelet aggregation and induces vasorelaxation without nitrate tolerance.