5-{imidazo[1,2-a]pyridin-6-yl}-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

• ChemBase ID: 172381
• Molecular Formular: C14H10N4O
• Molecular Mass: 250.2554
• Monoisotopic Mass: 250.08546096
• SMILES: c1c(cn2c(c1)ncc2)c1cc(c(=O)[nH]c1C)C#N
• Canonical SMILES: N#Cc1cc(c([nH]c1=O)C)c1ccc2n(c1)ccn2
• InChI: InChI=1S/C14H10N4O/c1-9-12(6-11(7-15)14(19)17-9)10-2-3-13-16-4-5-18(13)8-10/h2-6,8H,1H3,(H,17,19)
• InChIKey: JPAWFIIYTJQOKW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{imidazo[1,2-a]pyridin-6-yl}-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
• IUPAC Traditional name: olprinone
• Synonyms: 1,2-Dihydro-5-imidazo[1,2-a]pyridin-6-yl-6-methyl-2-oxo-3-pyridinecarbonitrile Hydrochloride; Olprinone Hydrochloride; Coretec; E 1020; Loprinone Hydrochloride

Database IDs

• CAS Number: 119615-63-3
• PubChem SID: 164228291
• PubChem CID: 4593

CALCULATED PROPERTIES

• Acid pKa: 7.5753675
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.46878245
• LogD (pH = 7.4): 0.075776406
• Log P: 0.116223864
• Molar Refractivity: 73.1734 cm^3
• Polarizability: 26.088959 Å^3
• Polar Surface Area: 70.19 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Off-White to Pale Beige Solid
• Melting Point: >290°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L469530

Inotropic agent which inhibits cAMP phosphodiesterase. Cardiotonic.

REFERENCES

• Tajimi, M., et al.: Arch. Pharmacol., 344, 602 (1991)
• Endoh, M., et al.: Cardiovasc. Drug Rev., 11, 432 (1991)
• Uemura, Y., et al.: J. Pharm. Pharmacol., 45, 1077 (1991)