N-[(3S,4S)-6-acetyl-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl]-3-chloro-4-fluorobenzamide

• ChemBase ID: 178741
• Molecular Formular: C20H19ClFNO4
• Molecular Mass: 391.8205632
• Monoisotopic Mass: 391.09866399
• SMILES: c1c(cc2c(c1)OC([C@H]([C@H]2NC(=O)c1ccc(c(c1)Cl)F)O)(C)C)C(=O)C
• Canonical SMILES: O=C(c1ccc(c(c1)Cl)F)N[C@H]1c2cc(ccc2OC([C@H]1O)(C)C)C(=O)C
• InChI: InChI=1S/C20H19ClFNO4/c1-10(24)11-5-7-16-13(8-11)17(18(25)20(2,3)27-16)23-19(26)12-4-6-15(22)14(21)9-12/h4-9,17-18,25H,1-3H3,(H,23,26)/t17-,18-/m0/s1
• InChIKey: XLIIRNOPGJTBJD-ROUUACIJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3S,4S)-6-acetyl-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl]-3-chloro-4-fluorobenzamide
• IUPAC Traditional name: N-[(3S,4S)-6-acetyl-3-hydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-4-yl]-3-chloro-4-fluorobenzamide
• Synonyms: N-[(3S,4S)-6-Acetyl-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl]-3-chloro-4-fluoro-benzamide; (3S-cis)-N-(6-acetyl-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)-3-chloro-4-fluorobenzamide; SB 220453; Tonabersat

Database IDs

• CAS Number: 175013-84-0
• PubChem SID: 164234651
• PubChem CID: 6918324

CALCULATED PROPERTIES

• Acid pKa: 12.042172
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.8738167
• LogD (pH = 7.4): 2.8738081
• Log P: 2.873817
• Molar Refractivity: 99.2536 cm^3
• Polarizability: 37.91006 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T539500

It is a cholinesterase inhibitor for treating and preventing migraine. An antimigraine agent.

REFERENCES

• Saito, R., et al.: Brain Res., 699, 109 (1995)
• Chan, W., et al.: Bioorg. Med. Chem. Lett., 9, 285 (1995)
• Nishida, M., et al.: Nature, 408, 492 (1995)
• Parsons, A., et al.: Br. J. Pharmacol., 132, 1549 (1995)