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

• ChemBase ID: 178581
• Molecular Formular: C22H30N6O3S2
• Molecular Mass: 490.642
• Monoisotopic Mass: 490.18208085
• SMILES: C1CN(CCN1S(=O)(=O)c1ccc(c(c1)c1nc2c(c(=S)[nH]1)n(nc2CCC)C)OCC)C
• Canonical SMILES: CCCc1nn(c2c1nc([nH]c2=S)c1cc(ccc1OCC)S(=O)(=O)N1CCN(CC1)C)C
• InChI: InChI=1S/C22H30N6O3S2/c1-5-7-17-19-20(27(4)25-17)22(32)24-21(23-19)16-14-15(8-9-18(16)31-6-2)33(29,30)28-12-10-26(3)11-13-28/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,32)
• InChIKey: LJUBVCQVNMLSTQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidine-7-thione
• IUPAC Traditional name: 5-[2-ethoxy-5-(4-methylpiperazin-1-ylsulfonyl)phenyl]-1-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidine-7-thione
• Synonyms: 5-[2-Ethoxy-5-[(4-methyl-1-piperazinyl)sulfonyl]phenyl]-1,6-dihydro-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidine-7-thione; 1-[[3-(4,7-Dihydro-1-methyl-3-propyl-7-thioxo-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-methylpiperazine; Thiosildenafil

Database IDs

• CAS Number: 479073-79-5
• PubChem SID: 164234491
• PubChem CID: 10228242

CALCULATED PROPERTIES

• Acid pKa: 11.5054655
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.6300739
• LogD (pH = 7.4): 2.2248564
• Log P: 2.2414596
• Molar Refractivity: 147.8648 cm^3
• Polarizability: 51.61684 Å^3
• Polar Surface Area: 92.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Pale Yellow Solid
• Melting Point: 172-174°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - T371500

An analog of Sildenafil; a novel pyrazolopyrimidinethiones as PDE5 inhibitor.

REFERENCES

• DeBono, R., et al.: Pharm. Technol., 26, 72 (2002)
• Blok-Tip, L., et al.: Food Addit. Contam., 21, 737 (2002)
• Liang, Q., et al.: J. Pharm. Biomed. Anal., 40, 305 (2002)