7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

• ChemBase ID: 67110
• Molecular Formular: C12H8ClFN2O3
• Molecular Mass: 282.6549232
• Monoisotopic Mass: 282.02074803
• SMILES: n1(cc(c(=O)c2cc(c(nc12)Cl)F)C(=O)O)C1CC1
• Canonical SMILES: OC(=O)c1cn(C2CC2)c2c(c1=O)cc(c(n2)Cl)F
• InChI: InChI=1S/C12H8ClFN2O3/c13-10-8(14)3-6-9(17)7(12(18)19)4-16(5-1-2-5)11(6)15-10/h3-5H,1-2H2,(H,18,19)
• InChIKey: OXNZWNNMJBOZQO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
• IUPAC Traditional name: 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid
• Synonyms: 3-Carboxy-7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine; 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic Acid; 1-Cyclopropyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid; 7-Chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Database IDs

• CAS Number: 100361-18-0
• MDL Number: MFCD08458865
• PubChem SID: 162032846
• PubChem CID: 11055142

CALCULATED PROPERTIES

• Acid pKa: 5.4151716
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.8370228
• LogD (pH = 7.4): 0.20529489
• Log P: 2.1823788
• Molar Refractivity: 66.7781 cm^3
• Polarizability: 24.214628 Å^3
• Polar Surface Area: 70.5 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95+%; 97%

DETAILS

Toronto Research Chemicals - C365115

Gemifloxacin intermediate as antibacterial agent.

REFERENCES

• Hoshino, K., et al.: Antimicrob. Agents Chemother., 38, 2623 (1994)
• Sanchez, J., et al.: J. Med. Chem., 38, 4478 (1994)
• Hong, C., et al.: Bioorg. Med. Chem. Lett., 8, 221 (1994)
• Zhanel, G., et al.: Drugs, 62, 13 (1994)