1087353-56-7

Basic information

• Product Name: 4-(((benzyloxy)carbonyl)amino)-2-fluorobenzoic acid
• Synonyms: 4-(((benzyloxy)carbonyl)amino)-2-fluorobenzoic acid
• CAS NO: 1087353-56-7
• Molecular Weight: 289.263
• Mol File: 1087353-56-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 412.9±45.0 °C(Predicted)
• Density: 1.402±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 4-(((benzyloxy)carbonyl)amino)-2-fluorobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(((benzyloxy)carbonyl)amino)-2-fluorobenzoic acid(1087353-56-7)
• EPA Substance Registry System: 4-(((benzyloxy)carbonyl)amino)-2-fluorobenzoic acid(1087353-56-7)

Safety Data

• Hazardous Substances Data: 1087353-56-7(Hazardous Substances Data)

Upstream product

• 157665-46-8 tert-butyl 2-fluoro-4-nitrobenzoate 
• 140373-77-9 tert-butyl 2-fluoro-4-aminobenzoate 
• 403-24-7 2-fluoro-4-nitrobenzoic acid 
• 1427-07-2 2-fluoro-4-nitrotoluene 
• 446-31-1 2-fluoro-4-aminobenzoic acid 
• 501-53-1 benzyl chloroformate 
• 324788-98-9 tert-butyl 4-benzyloxycarbonylamino-2-fluoro-benzoate 

Downstream Products

• 1087353-59-0 benzyl [3-fluoro-4-(4-hydroxymethyl-oxazol-2-yl)-phenyl]-carbamate 
• 1087353-67-0 5-(R)-azidomethyl-3-[4-(4-chloromethyl-oxazol-2-yl)-3-fluoro-phenyl]-oxazolidin-2-one 
• 1087353-66-9 5-(R)-azidomethyl-3-[3-fluoro-4-(4-hydroxymethyl-oxazol-2-yl)-phenyl]-oxazolidin-2-one 
• 1087354-00-4 methyl 2-(4-benzyloxycarbonylamino-2-fluoro-phenyl)-4,5-oxazole-4-carboxylate 
• 1087353-97-6 C₁₇H₁₆FN₅O₃ 
• 1087352-55-3 5-(R)-azidomethyl-3-[3-fluoro-4-(4-[1,2,4]triazol-1-ylmethyl-oxazol-2-yl)-phenyl]-oxazolidin-2-one 
• 1087352-53-1 5-(R)-azidomethyl-3-[3-fluoro-4-(4-pyrazol-1-ylmethyl-oxazol-2-yl)-phenyl]-oxazolidin-2-one 
• 1087352-56-4 N-{3-[3-fluoro-4-(4-[1,2,4]triazol-1-ylmethyl-oxazol-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
• 1087352-54-2 N-{3-[3-fluoro-4-(4-pyrazol-1-ylmethyl-oxazol-2-yl)-phenyl]-2-oxo-oxazolidin-5(S)-ylmethyl}-acetamide 
• 1087353-60-3 benzyl {4-[4-(tert-butyl-dimethyI-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-carbamate 
• 1087353-62-5 3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-5-(R)-hydroxymethyl-oxazolidin-2-one 
• 1087353-65-8 5-(R)-azidomethyl-3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-oxazolidin-2-one 
• 1087353-64-7 3-{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-2-yl]-3-fluoro-phenyl}-2-oxo-oxazolidin-5-yImethyl methanesulfonate 

Relevant articles and documents

Compound design guidelines for evading the efflux and permeation barriers of Escherichia coli with the oxazolidinone class of antibacterials: Test case for a general approach to improving whole cell Gram-negative activity

Previously we reported the results from an effort to improve Gram-negative antibacterial activity in the oxazolidinone class of antibiotics via a systematic medicinal chemistry campaign focused entirely on C-ring modifications. In that series we set about testing if the efflux and permeation barriers intrinsic to the outer membrane of Escherichia coli could be rationally overcome by designing analogs to reside in specific property limits associated with Gram-negative activity: i) low MW (7.4 1), and iii) zwitterionic character at pH 7.4. Indeed, we observed that only analogs residing within these limits were able to overcome these barriers. Herein we report the results from a parallel effort where we explored structural changes throughout all three rings in the scaffold for the same purpose. Compounds were tested against a diagnostic MIC panel of Escherichia coli and Staphylococcus aureus strains to determine the impact of combining structural modifications in overcoming the OM barriers and in bridging the potency gap between the species. The results demonstrated that distributing the charge-carrying moieties across two rings was also beneficial for avoidance of the outer membrane barriers. Importantly, analysis of the structure-permeation relationship (SPR) obtained from this and the prior study indicated that in addition to MW, polarity, and zwitterionic character, having ≤4 rotatable bonds is also associated with evasion of the OM barriers. These combined results provide the medicinal chemist with a framework and strategy for overcoming the OM barriers in GNB in antibacterial drug discovery efforts.