2-[8-(benzyloxy)-2-methylimidazo[1,2-a]pyridin-3-yl]acetonitrile

• ChemBase ID: 154166
• Molecular Formular: C17H15N3O
• Molecular Mass: 277.3205
• Monoisotopic Mass: 277.12151212
• SMILES: Cc1c(n2cccc(c2n1)OCc1ccccc1)CC#N
• Canonical SMILES: N#CCc1c(C)nc2n1cccc2OCc1ccccc1
• InChI: InChI=1S/C17H15N3O/c1-13-15(9-10-18)20-11-5-8-16(17(20)19-13)21-12-14-6-3-2-4-7-14/h2-8,11H,9,12H2,1H3
• InChIKey: PYKJFEPAUKAXNN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[8-(benzyloxy)-2-methylimidazo[1,2-a]pyridin-3-yl]acetonitrile
• IUPAC Traditional name: 2-[8-(benzyloxy)-2-methylimidazo[1,2-a]pyridin-3-yl]acetonitrile
• Synonyms: 2-methyl-8-(phenylmethoxy)imidazo[1,2-a]pyridine-3-acetonitrile; SCH-28080

Database IDs

• CAS Number: 76081-98-6
• MDL Number: MFCD00834620
• PubChem SID: 24278810; 162248305
• PubChem CID: 108137

CALCULATED PROPERTIES

• Acid pKa: 13.060046
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.8930109
• LogD (pH = 7.4): 2.0705664
• Log P: 2.0734198
• Molar Refractivity: 81.7681 cm^3
• Polarizability: 30.684528 Å^3
• Polar Surface Area: 50.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble >10 mg/mL; H2O: insoluble
• Apperance: white to light tan solid

Safety Information

• Storage Condition: desiccated
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H15N3O

DETAILS

Sigma Aldrich - S4443

Biochem/physiol Actions
SCH-28080 is a potent inhibitor of gastric H+ and K+-ATPase. The novel antiulcer agents, SCH-28080 and SCH-32651 were examined for their ability to inhibit the H+K+ ATPase enzyme activity in a preparation of microsomal membranes from rabbit fundic mucosa. SCH- 28080 inhibited the isolated enzyme activity with a potency similar to omeprazole, IC50s of 2.5 and 4.0 μM respectively. SCH 32651 was less potent exhibiting an IC50 of 200.0 μM. Both compounds may therefore exert their antisecretory activity via a direct inhibition of the parietal cell H+K+ ATPase.