3-{1-methyl-7-oxo-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-5-yl}-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-propoxybenzene-1-sulfonamide

• ChemBase ID: 179376
• Molecular Formular: C25H36N6O4S
• Molecular Mass: 516.65614
• Monoisotopic Mass: 516.25187466
• SMILES: c1cc(cc(c1OCCC)c1nc2c(c(=O)[nH]1)n(nc2CCC)C)S(=O)(=O)NCCC1CCCN1C
• Canonical SMILES: CCCOc1ccc(cc1c1nc2c(CCC)nn(c2c(=O)[nH]1)C)S(=O)(=O)NCCC1CCCN1C
• InChI: InChI=1S/C25H36N6O4S/c1-5-8-20-22-23(31(4)29-20)25(32)28-24(27-22)19-16-18(10-11-21(19)35-15-6-2)36(33,34)26-13-12-17-9-7-14-30(17)3/h10-11,16-17,26H,5-9,12-15H2,1-4H3,(H,27,28,32)
• InChIKey: IYFNEFQTYQPVOC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{1-methyl-7-oxo-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-5-yl}-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-propoxybenzene-1-sulfonamide
• IUPAC Traditional name: udenafil
• Synonyms: (αS)-α-Amino-3-[(4-carboxyphenyl)methyl]-3,4-dihydro-5-iodo-2,4-dioxo-1(2H)-pyrimidinepropanoic acid; UBP 301

Database IDs

• CAS Number: 569371-10-4
• PubChem SID: 164235286
• PubChem CID: 6918523

CALCULATED PROPERTIES

• Acid pKa: 9.070208
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.4836102
• LogD (pH = 7.4): 1.2659689
• Log P: 1.9681323
• Molar Refractivity: 153.5468 cm^3
• Polarizability: 53.79364 Å^3
• Polar Surface Area: 117.92 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - U103500

UBP 301 is an antagonist of kainate receptors. UBP 301 is the N3-4-carboxybenzyl substituted analog II of Willardiine, which was found to be equipotent at AMPA and GLUK5-containing kainate receptors in the neonatal rat spinal cord.

REFERENCES

• Fletcher, E., et al.: Pharmacol. Ther., 70, 65 (1996)
• Bleakman, D., et al.: Neuropharmacology, 37, 1187 (1996)
• Chittajallu, R., et al.: Trends Pharmacol. Sci., 20, 26 (1996)
• Valgeirsson, J., et al.: J. Med. Chem., 47, 6948 (1996)