5-(2-ethoxy-5-{[4-(2H3)methylpiperazin-1-yl]sulfonyl}phenyl)-2-methyl-3-propyl-2H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one

• ChemBase ID: 171957
• Molecular Formular: C22H30N6O4S
• Molecular Mass: 474.5764
• Monoisotopic Mass: 474.20492447
• SMILES: C1N(CCN(C1)S(=O)(=O)c1ccc(c(c1)c1nc2c(c(=O)[nH]1)nn(c2CCC)C)OCC)C
• Canonical SMILES: CCCc1n(C)nc2c1nc([nH]c2=O)c1cc(ccc1OCC)S(=O)(=O)N1CCN(CC1)C
• InChI: InChI=1S/C22H30N6O4S/c1-5-7-17-19-20(25-27(17)4)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)
• InChIKey: AEHJOHLAUWUPQW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(2-ethoxy-5-{[4-(^2H₃)methylpiperazin-1-yl]sulfonyl}phenyl)-2-methyl-3-propyl-2H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one
• IUPAC Traditional name: 5-{2-ethoxy-5-[4-(^2H₃)methylpiperazin-1-ylsulfonyl]phenyl}-2-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-7-one
• Synonyms: 5-[2-Ethoxy-5-[(4-(methyl-d3)-1-piperazinyl)sulfonyl]phenyl]-2,6-dihydro-2-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one; 1-[[3-(4,7-Dihydro-2-methyl-7-oxo-3-propyl-2H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-(methyl-d3)piperazine; Iso Sildenafil-d3

Database IDs

• PubChem SID: 164227867
• PubChem CID: 71749627

CALCULATED PROPERTIES

• Acid pKa: 8.272948
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 1.09671
• LogD (pH = 7.4): 1.6429406
• Log P: 1.7076169
• Molar Refractivity: 140.0797 cm^3
• Polarizability: 48.2957 Å^3
• Polar Surface Area: 109.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Yellow Solid
• Melting Point: 203-205°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - I900802

Labelled Iso Sildenafil (I900800). Isosildenafil is the isomer of Sildenafil methylated at N-2 position of the pyrazolo[4,3-d]pyrimidin-7-one nucleus.

REFERENCES

• Sheldrick, G., et al.: Acta Crystallogr., A46, 467 (1990)
• Terrett, N., et al.: Bioorg. Med. Chem. Lett., 6, 1819 (1990)