5-(2-propoxyphenyl)-3H,6H,7H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one

• ChemBase ID: 179627
• Molecular Formular: C13H13N5O2
• Molecular Mass: 271.27462
• Monoisotopic Mass: 271.10692468
• SMILES: [nH]1c(nc2c(c1=O)nn[nH]2)c1c(cccc1)OCCC
• Canonical SMILES: CCCOc1ccccc1c1[nH]c(=O)c2c(n1)[nH]nn2
• InChI: InChI=1S/C13H13N5O2/c1-2-7-20-9-6-4-3-5-8(9)11-14-12-10(13(19)15-11)16-18-17-12/h3-6H,2,7H2,1H3,(H2,14,15,16,17,18,19)
• InChIKey: REZGGXNDEMKIQB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(2-propoxyphenyl)-3H,6H,7H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
• IUPAC Traditional name: 5-(2-propoxyphenyl)-3H,6H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
• Synonyms: 3,6-dihydro-5-(2-propoxyphenyl)-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one; 1,4-Dihydro-5-[2-propoxyphenyl]-7H-1,2,3-triazolo[4,5-d]pyrimidine-7-one; 8-Aza-2-(2-propoxyphenyl)-6-purinone; M&B 22,948; Zaprinast

Database IDs

• CAS Number: 37762-06-4
• PubChem SID: 164235537
• PubChem CID: 5722

CALCULATED PROPERTIES

• Acid pKa: 6.5769415
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.7136773
• LogD (pH = 7.4): 0.9291856
• Log P: 1.7477235
• Molar Refractivity: 74.7219 cm^3
• Polarizability: 26.77007 Å^3
• Polar Surface Area: 92.26 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Pink Solid
• Melting Point: 237-238°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - Z150000

A selective inhibitor of cyclic-GMP phosphodiesterase (PDE V, calmodulin insensitive). Since cGMP mediates the vasorelaxant action of nitric oxide, as well as the natriuretic and diuretic effect of atrial natriuretic factor (ANF) through the activation of

REFERENCES

• Burns, F., et al.: Biochem. J., 238, 487 (1992)
• Lugnier, C., et al.: Am. J. Physiol., 262, H654 (1992)