3,5-diethyl 4-{2-[(1Z)-3-(tert-butoxy)-3-oxoprop-1-en-1-yl]phenyl}-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

• ChemBase ID: 172153
• Molecular Formular: C26H33NO6
• Molecular Mass: 455.54332
• Monoisotopic Mass: 455.23078778
• SMILES: N1C(=C(C(C(=C1C)C(=O)OCC)c1ccccc1/C=C\C(=O)OC(C)(C)C)C(=O)OCC)C
• Canonical SMILES: CCOC(=O)C1=C(C)NC(=C(C1c1ccccc1/C=C\C(=O)OC(C)(C)C)C(=O)OCC)C
• InChI: InChI=1S/C26H33NO6/c1-8-31-24(29)21-16(3)27-17(4)22(25(30)32-9-2)23(21)19-13-11-10-12-18(19)14-15-20(28)33-26(5,6)7/h10-15,23,27H,8-9H2,1-7H3/b15-14-
• InChIKey: GKQPCPXONLDCMU-PFONDFGASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,5-diethyl 4-{2-[(1Z)-3-(tert-butoxy)-3-oxoprop-1-en-1-yl]phenyl}-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• IUPAC Traditional name: 3,5-diethyl 4-{2-[(1Z)-3-(tert-butoxy)-3-oxoprop-1-en-1-yl]phenyl}-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• Synonyms: (Z)-4-[2-[3-(1,1-Dimethylethoxy)-3-oxo-1-propenyl]phenyl]-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic Acid Diethyl Ester; cis Lacidipine

Database IDs

• CAS Number: 103890-79-5
• PubChem SID: 164228063
• PubChem CID: 12989341

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.9171872
• LogD (pH = 7.4): 4.1805105
• Log P: 4.1851535
• Molar Refractivity: 129.9138 cm^3
• Polarizability: 49.212093 Å^3
• Polar Surface Area: 90.93 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L097995

Z-Isomer of Lacidipine; a dihydropyridine calcium channel blocker. Antihypertensive.

REFERENCES

• Safar, M., et al.: Clin. Pharmacol. Ther., 46, 94 (1989)
• Kharat, V.R., et al.: J. Pharm. Biomed. Anal., 28, 789 (1989)
• McCormack, A.J., et al.: Drugs, 63, 2327 (1989)