1-(2-chlorophenyl)-6-[(2R)-3,3,3-trifluoro-2-methylpropyl]-1H,4H,5H-pyrazolo[3,4-d]pyrimidin-4-one

• ChemBase ID: 153855
• Molecular Formular: C15H12ClF3N4O
• Molecular Mass: 356.7301896
• Monoisotopic Mass: 356.06517336
• SMILES: C[C@H](Cc1[nH]c(=O)c2cnn(c2n1)c1ccccc1Cl)C(F)(F)F
• Canonical SMILES: C[C@@H](C(F)(F)F)Cc1[nH]c(=O)c2c(n1)n(nc2)c1ccccc1Cl
• InChI: InChI=1S/C15H12ClF3N4O/c1-8(15(17,18)19)6-12-21-13-9(14(24)22-12)7-20-23(13)11-5-3-2-4-10(11)16/h2-5,7-8H,6H2,1H3,(H,21,22,24)/t8-/m1/s1
• InChIKey: FFPXPXOAFQCNBS-MRVPVSSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(2-chlorophenyl)-6-[(2R)-3,3,3-trifluoro-2-methylpropyl]-1H,4H,5H-pyrazolo[3,4-d]pyrimidin-4-one
• IUPAC Traditional name: 1-(2-chlorophenyl)-6-[(2R)-3,3,3-trifluoro-2-methylpropyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one
• Synonyms: 1-(2-Chlorophenyl)-6-[(2R)-3,3,3-trifluoro-2-methylpropyl]-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidine-4-one; BAY 73-6691

Database IDs

• CAS Number: 794568-92-6
• MDL Number: MFCD08705319
• PubChem SID: 162247994; 24724419
• PubChem CID: 16078952

CALCULATED PROPERTIES

• Acid pKa: 9.204311
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.2619364
• LogD (pH = 7.4): 3.256027
• Log P: 3.2620127
• Molar Refractivity: 84.4441 cm^3
• Polarizability: 30.715345 Å^3
• Polar Surface Area: 59.28 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

• European Hazard Symbols: Toxic (T); Irritant (Xi)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-36/37/38
• Safety Statements: 26-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H315-H319-H335-H413
• GHS Precautionary statements: P261-P264-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C15H12ClF3N4O

DETAILS

Sigma Aldrich - B3561

Biochem/physiol Actions
BAY 73-6691 was characterized in vitro as the first potent and selective inhibitor of phosphodiesterase 9 (PDE9), which is currently under preclinical development for the treatment of Alzheimer′s disease. This compound selectively inhibits human (IC50 = 55 nM) and murine (IC50 = 100 nM) PDE9 activity in vitro and shows only moderate activity against other cyclic nucleotide-specific phosphodiesterases. BAY 73-6691 alone did not significantly increase basal cGMP levels. The PDE9 inhibitor significantly potentiated the cGMP signals generated by sGC activating compounds such as BAY 58-2667 or 5-cyclopropyl-2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-4-ylamine (BAY 41-2272) and induced leftward shifts of the corresponding concentration-response curves. The newly generated PDE9 reporter cell line show that BAY 73-6691 is able to efficiently penetrate cells and to inhibit intracellular PDE9 activity.†