5-(2-ethoxy-5-{[4-(2-hydroxyethyl)piperazin-1-yl]sulfonyl}phenyl)-1-methyl-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one

• ChemBase ID: 170637
• Molecular Formular: C23H32N6O5S
• Molecular Mass: 504.60238
• Monoisotopic Mass: 504.21548915
• SMILES: n1c([nH]c2c(c1=O)n(nc2CCC)C)c1cc(ccc1OCC)S(=O)(=O)N1CCN(CC1)CCO
• Canonical SMILES: CCCc1nn(c2c1[nH]c(nc2=O)c1cc(ccc1OCC)S(=O)(=O)N1CCN(CC1)CCO)C
• InChI: InChI=1S/C23H32N6O5S/c1-4-6-18-20-21(27(3)26-18)23(31)25-22(24-20)17-15-16(7-8-19(17)34-5-2)35(32,33)29-11-9-28(10-12-29)13-14-30/h7-8,15,30H,4-6,9-14H2,1-3H3,(H,24,25,31)
• InChIKey: NEYKRKVLEWKOBI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(2-ethoxy-5-{[4-(2-hydroxyethyl)piperazin-1-yl]sulfonyl}phenyl)-1-methyl-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one
• IUPAC Traditional name: 5-{2-ethoxy-5-[4-(2-hydroxyethyl)piperazin-1-ylsulfonyl]phenyl}-1-methyl-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-7-one
• Synonyms: 5-[2-Ethoxy-5-[[4-(2-hydroxyethyl)-1-piperazinyl]sulfonyl]phenyl]-1,6-dihydro-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one; Lodenafil; Hydroxyhomo Sildenafil

Database IDs

• CAS Number: 139755-85-4
• PubChem SID: 164226547
• PubChem CID: 4742795

CALCULATED PROPERTIES

• Acid pKa: 7.2645335
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): 0.67159647
• LogD (pH = 7.4): 0.813744
• Log P: 0.96818656
• Molar Refractivity: 145.7328 cm^3
• Polarizability: 50.984146 Å^3
• Polar Surface Area: 129.36 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Pale Yellow Solid
• Melting Point: 183-185°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H942840

A Sildenafil (S435000) analog, enhances male sexual function

REFERENCES

• Antunes, J., et al.: Bioorg. Med. Chem., 16, 7599 (2008)
• Toque, H., et al.: Eur. J. Pharmacol., 591, 189 (2008)