179741-09-4

Basic information

• Product Name: ethyl 1-(3-tert-butyloxycarbonylamino-4,6-difluorophenyl)-8-bromo-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate
• Synonyms: ethyl 1-(3-tert-butyloxycarbonylamino-4,6-difluorophenyl)-8-bromo-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate
• CAS NO: 179741-09-4
• Molecular Weight: 559.312
• Mol File: 179741-09-4.mol

Chemical Properties

• CAS DataBase Reference: ethyl 1-(3-tert-butyloxycarbonylamino-4,6-difluorophenyl)-8-bromo-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 1-(3-tert-butyloxycarbonylamino-4,6-difluorophenyl)-8-bromo-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate(179741-09-4)
• EPA Substance Registry System: ethyl 1-(3-tert-butyloxycarbonylamino-4,6-difluorophenyl)-8-bromo-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate(179741-09-4)

Safety Data

• Hazardous Substances Data: 179741-09-4(Hazardous Substances Data)

Upstream product

• 153775-33-8 2,4-difluoro-5-nitro-benzoic acid 
• 1583-58-0 2,4-difluoro-benzoic acid 
• 112811-54-8 (Z)-2-(3-Bromo-2-chloro-4,5-difluoro-benzoyl)-3-ethoxy-acrylic acid ethyl ester 
• 112062-53-0 ethyl 2-(3-bromo-2-chloro-4,5-difluorobenzoyl)acetate 
• 179741-61-8 tert-butyl (2,4-difluoro-5-nitrophenyl)carbamate 
• 179741-60-7 tert-butyl (5-amino-2,4-difluorophenyl)carbamate 
• 221560-09-4 2,4-Difluoro-5-nitrobenzoyl Chloride 

Downstream Products

• 179741-10-7 1-(5-amino-2,4-difluorophenyl)-8-bromo-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 

Relevant articles and documents

A novel antibacterial 8-chloroquinolone with a distorted orientation of the N1-(5-amino-2,4-difluorophenyl) group

Fluoroquinolones represent a major class of antibacterial agents with great therapeutic potential. In this study, we designed m-aminophenyl groups as novel N-1 substituents of naphthyridones and quinolones. Among newly synthesized compounds, 7-(3-aminoazetidin-1-yl)-1-(5-amino-2,4-difluorophenyl)-8-chloro-6- fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (4) has extremely potent antibacterial activities against Gram (+) as well as Gram (-) bacteria. This compound is significantly more potent than trovafloxacin against clinical isolates: 30 times against Streptococcus pneumoniae and 128 times against methicillin resistant Staphylococcus aureus. The structure-activity relationship (SAR) study revealed that a limited combination of 1-(5-amino-2,4-difluorophenyl) group, 7-(azetidin-1-yl) group, and 8-Cl atom (or Br atom or Me group) gave potent antibacterial activity. An X-ray crystallographic study of a 7-(3-ethylaminoazetidin-1-yl)-8-chloro derivative demonstrated that the N-1 aromatic group was remarkably distorted out of the core quinolone plane by steric repulsion between the C-8 Cl atom and the N-1 substituent. Furthermore, a molecular modeling study of 4 and its analogues demonstrated that a highly distorted orientation was induced by a steric hindrance of the C-8 substituent, such as Cl, Br, or a methyl group. Thus, their highly strained conformation should be a key factor for the potent antibacterial activity.

Pyridonecarboxylic acid derivatives or salts thereof and antibacterial agents comprising the same as active ingredient

The invention provides a pyridonecarboxylic acid derivative of the following general formula (1): STR1 wherein R1 is a hydrogen atom or carboxy protecting group, R2 is a nitro or substituted or unsubstituted amino group, R3/sup