3-methyl 5-(2E)-3-phenylprop-2-en-1-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

• ChemBase ID: 176798
• Molecular Formular: C25H24N2O6
• Molecular Mass: 448.46786
• Monoisotopic Mass: 448.1634365
• SMILES: C1(=C(NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OC/C=C/c1ccccc1)C)C)C(=O)OC
• Canonical SMILES: COC(=O)C1=C(C)NC(=C(C1c1cccc(c1)[N+](=O)[O-])C(=O)OC/C=C/c1ccccc1)C
• InChI: InChI=1S/C25H24N2O6/c1-16-21(24(28)32-3)23(19-12-7-13-20(15-19)27(30)31)22(17(2)26-16)25(29)33-14-8-11-18-9-5-4-6-10-18/h4-13,15,23,26H,14H2,1-3H3/b11-8+
• InChIKey: XTFPDGZNWTZCMF-DHZHZOJOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methyl 5-(2E)-3-phenylprop-2-en-1-yl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• IUPAC Traditional name: pranidipine
• Synonyms: 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic Acid 3-Methyl 5-[(2E)-3-phenyl-2-propen-1-yl] Ester; FRC 8411; OPC 13340; Pranidipine

Database IDs

• CAS Number: 99522-79-9
• PubChem SID: 164232708
• PubChem CID: 6436048

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.888888
• LogD (pH = 7.4): 4.1453996
• Log P: 4.1498833
• Molar Refractivity: 127.0959 cm^3
• Polarizability: 47.016575 Å^3
• Polar Surface Area: 110.45 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: 140-142°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - P700950

A novel calcium channel antagonist; cardiovascular agent.

REFERENCES

• Matsumori, A., et al.: Circulation, 66, 355 (1982)
• Roberts, W., et al.: Am. J. Cardiol., 60, 1340 (1982)
• Uehara, Y., et al.: J. Cardiovasc. Pharmacol., 23, 970 (1982)
• Kim, C., et al.: Cardiovasc. Drugs Ther., 13, 455 (1982)
• Watanabe, K., et al.: Br. J