4-chloro-N-[(2S)-2-{[(1R)-1-(naphthalen-1-yl)ethyl]amino}cyclohexyl]benzamide

• ChemBase ID: 163547
• Molecular Formular: C25H27ClN2O
• Molecular Mass: 406.94768
• Monoisotopic Mass: 406.18119117
• SMILES: c1c(ccc(c1)C(=O)NC1CCCC[C@@H]1N[C@@H](c1cccc2c1cccc2)C)Cl
• Canonical SMILES: Clc1ccc(cc1)C(=O)NC1CCCC[C@@H]1N[C@@H](c1cccc2c1cccc2)C
• InChI: InChI=1S/C25H27ClN2O/c1-17(21-10-6-8-18-7-2-3-9-22(18)21)27-23-11-4-5-12-24(23)28-25(29)19-13-15-20(26)16-14-19/h2-3,6-10,13-17,23-24,27H,4-5,11-12H2,1H3,(H,28,29)/t17-,23+,24?/m1/s1
• InChIKey: YTFUQWWKTIWYEY-GYUIMPAFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-chloro-N-[(2S)-2-{[(1R)-1-(naphthalen-1-yl)ethyl]amino}cyclohexyl]benzamide
• IUPAC Traditional name: 4-chloro-N-[(2S)-2-{[(1R)-1-(naphthalen-1-yl)ethyl]amino}cyclohexyl]benzamide
• Synonyms: 4-Chloro-N-[(1S,2S)-2-[[(1R)-1-(1-naphthalenyl)ethyl]amino]cyclohexyl]benzamide; Calhex 231

Database IDs

• CAS Number: 652973-93-8
• PubChem SID: 162257682
• PubChem CID: 71314479

CALCULATED PROPERTIES

• Acid pKa: 14.822587
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.63609
• LogD (pH = 7.4): 3.5820067
• Log P: 5.832197
• Molar Refractivity: 119.1273 cm^3
• Polarizability: 47.696568 Å^3
• Polar Surface Area: 41.13 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ether; Ethyl Acetate; Hexanes; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 53-55°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C148000

A new calcium sensing receptor ligand demonstrating potent calcilytic activity.

REFERENCES

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• Sato, M., et al.: J. Med. Chem., 42, 1 (1997)
• Rodan, G., et al.: Science, 289, 1508 (1997)
• Goltzman, D., et al.: Nat. Rev. Drug Discov., 1, 784 (1997)
• Petrel, C., et al.: J. Biol. Chem., 279, 18990 (2