1-cyclopropyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

• ChemBase ID: 165388
• Molecular Formular: C18H19F2N3O3
• Molecular Mass: 363.3585664
• Monoisotopic Mass: 363.13944792
• SMILES: c1(c(c(cc2c1n(cc(c2=O)C(=O)O)C1CC1)F)N1CC(NCC1)C)F
• Canonical SMILES: CC1NCCN(C1)c1c(F)cc2c(c1F)n(cc(c2=O)C(=O)O)C1CC1
• InChI: InChI=1S/C18H19F2N3O3/c1-9-7-22(5-4-21-9)16-13(19)6-11-15(14(16)20)23(10-2-3-10)8-12(17(11)24)18(25)26/h6,8-10,21H,2-5,7H2,1H3,(H,25,26)
• InChIKey: ZHKOPMSOBOQYRH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-cyclopropyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• IUPAC Traditional name: 1-cyclopropyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
• Synonyms: 1-Cyclopropyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid; AMQ 2; CP 105532; 8-Demethoxy-8-fluoro Gatifloxacin

Database IDs

• CAS Number: 103460-89-5
• PubChem SID: 162259521
• PubChem CID: 462061

CALCULATED PROPERTIES

• Acid pKa: 5.6477804
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.56258637
• LogD (pH = 7.4): -0.28234303
• Log P: -0.280212
• Molar Refractivity: 92.5746 cm^3
• Polarizability: 33.86135 Å^3
• Polar Surface Area: 72.88 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D230800

A fluoroquinolone used in the synthesis of Gatifloxacin (G250000).

REFERENCES

• Sunderland, J., et al.: J. Antimicrob. Chemother., 47, 271 (2001)
• Herzler, M., et al.: J. Anal. Toxicol., 27, 233 (2001)
• Li, Y., et al.: J. Pharm. Biomed. Anal., 35, 1101 (2001)