2-[(3,4-dimethoxyphenyl)methyl]-7-[(2R,3R)-2-hydroxy-6-phenylhexan-3-yl]-5-methyl-1H,4H-imidazo[4,3-f][1,2,4]triazin-4-one

• ChemBase ID: 161116
• Molecular Formular: C27H32N4O4
• Molecular Mass: 476.56738
• Monoisotopic Mass: 476.24235552
• SMILES: c1c(c(cc(c1)Cc1nc(=O)c2n([nH]1)c(nc2C)[C@H]([C@H](O)C)CCCc1ccccc1)OC)OC
• Canonical SMILES: COc1cc(ccc1OC)Cc1nc(=O)c2n([nH]1)c(nc2C)[C@H]([C@H](O)C)CCCc1ccccc1
• InChI: InChI=1S/C27H32N4O4/c1-17-25-27(33)29-24(16-20-13-14-22(34-3)23(15-20)35-4)30-31(25)26(28-17)21(18(2)32)12-8-11-19-9-6-5-7-10-19/h5-7,9-10,13-15,18,21,32H,8,11-12,16H2,1-4H3,(H,29,30,33)/t18-,21+/m1/s1
• InChIKey: MYTWFJKBZGMYCS-NQIIRXRSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3,4-dimethoxyphenyl)methyl]-7-[(2R,3R)-2-hydroxy-6-phenylhexan-3-yl]-5-methyl-1H,4H-imidazo[4,3-f][1,2,4]triazin-4-one
• IUPAC Traditional name: 2-[(3,4-dimethoxyphenyl)methyl]-7-[(2R,3R)-2-hydroxy-6-phenylhexan-3-yl]-5-methyl-1H-imidazo[4,3-f][1,2,4]triazin-4-one
• Synonyms: 2-[(3,4-Dimethoxyphenyl)methyl]-7-[(1R)-1-[(1R)-1-hydroxyethyl]-4-phenylbutyl]-5-methyl-imidazo[5,1-f][1,2,4]triazin-4(1H)-one; Bay 60-7550

Database IDs

• CAS Number: 439083-90-6
• PubChem SID: 162255251
• PubChem CID: 25273570

CALCULATED PROPERTIES

• Acid pKa: 8.063056
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 3.3373823
• LogD (pH = 7.4): 3.261217
• Log P: 3.3385675
• Molar Refractivity: 145.7907 cm^3
• Polarizability: 51.361237 Å^3
• Polar Surface Area: 97.97 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B119000

The compound induced anxiety by inhibition of Phosphodiesterase-2 (PDE2), which regulates cGMP and cAMP signaling.

REFERENCES

• Deguchi, A., et al.: Mol. Cancer Ther., 1, 803 (2002)
• Masood, A., et al.: Eur. J. Pharmacol., 458, 135 (2002)
• Hovatta, I., et al.: Nature, 438, 662 (2002)
• Nikolaev, V., et al.: J. Biol. Chem., 280, 1716 (2002)
• Bouayed, J., et al.: Eur. J. Pharmacol.,