7-[(4aS,7aS)-octahydropyrrolo[3,4-b]morpholin-6-yl]-8-cyano-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride

• ChemBase ID: 168920
• Molecular Formular: C20H20ClFN4O4
• Molecular Mass: 434.8486032
• Monoisotopic Mass: 434.11571104
• SMILES: c1(c(c(c2c(c1)c(=O)c(cn2C1CC1)C(=O)O)C#N)N1C[C@H]2[C@H](C1)NCCO2)F.Cl
• Canonical SMILES: N#Cc1c(N2C[C@H]3[C@H](C2)NCCO3)c(F)cc2c1n(cc(c2=O)C(=O)O)C1CC1.Cl
• InChI: InChI=1S/C20H19FN4O4.ClH/c21-14-5-11-17(25(10-1-2-10)7-13(19(11)26)20(27)28)12(6-22)18(14)24-8-15-16(9-24)29-4-3-23-15;/h5,7,10,15-16,23H,1-4,8-9H2,(H,27,28);1H/t15-,16-;/m0./s1
• InChIKey: CQMSQUOHWYYEKM-MOGJOVFKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(4aS,7aS)-octahydropyrrolo[3,4-b]morpholin-6-yl]-8-cyano-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride
• IUPAC Traditional name: 7-[(4aS,7aS)-hexahydro-2H-pyrrolo[3,4-b]morpholin-6-yl]-8-cyano-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid hydrochloride
• Synonyms: 8-Cyano-1-cyclopropyl-6-fluoro-7-[(4aS,7aS)-hexahydropyrrolo[3,4-b]-1,4-oxazin-6(2H)-yl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Hydrochloride; Finafloxacin Hydrochloride

Database IDs

• CAS Number: 209342-41-6
• PubChem SID: 162263052
• PubChem CID: 11662028

CALCULATED PROPERTIES

• Acid pKa: 4.5203733
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.0925965
• LogD (pH = 7.4): -1.2682623
• Log P: -1.0753613
• Molar Refractivity: 102.0759 cm^3
• Polarizability: 37.81362 Å^3
• Polar Surface Area: 105.9 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F338000

Used for preparation of naphthyridonecarboxylic acid derivatives as drugs for therapy of Helicobacter pylori infections and associated gastroduodenal illnesses.

REFERENCES

• Hooper, D.C., et al.: Engl. J. Med., 324, 384 (1991)
• Montecucco, C., et al.: Microbes Infect., 5, 715 (1991)
• Vicente, F.R.C., et al.: Bioorg. Med. Chem. Lett., 17, 5661 (1991)