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Chemistry
Organic Building Blocks
Fluorinated Building Blocks
fluorophenylisocyanate
3-Fluorophenylisocyanate
Chemistry
Organic Building Blocks
Fluorinated Building Blocks
Isocyanates and Isothiocyanates Benzene Compounds
fluorophenylisocyanate

[ CAS No. 404-71-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 404-71-7
Chemical Structure| 404-71-7
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Quality Control of [ 404-71-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
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Product Citations

Product Citations

Canale, Vittorio ; Czekajewska, Joanna ; Klesiewicz, Karolina , et al. DOI: PubMed ID:

Abstract: The alarming increase in the resistance of bacteria to the currently available antibiotics necessitates the development of new effective antimicrobial agents that are active against bacterial pathogens causing major public health problems. For this purpose, our inhouse libraries were screened against a wide panel of clin. relevant Gram-pos. and Gram-neg. bacteria, based on which compound I was selected for further optimization. Synthetic efforts in a group of arylurea derivatives of aryloxy(1-phenylpropyl) alicyclic diamines, followed with an in vitro evaluation of the activity against multidrug-resistant strains identified compound 44 (1-(3-chlorophenyl)-3-(1-{3-phenyl-3-[3-(trifluoromethyl)phenoxy] propyl}piperidin-4-yl)urea). Compound 44 showed antibacterial activity against Gram-pos. bacteria including fatal drug-resistant strains i.e., Staphylococcus aureus (methicillin-resistant, MRSA; vancomycin-intermediate, VISA) and Enterococcus faecium (vancomycin-resistant, VREfm) at low concentrations (0.78-3.125 μg/mL) comparable to last resort antibiotics (i.e., vancomycin and linezolid). It is also potent against biofilm-forming S. aureus and Staphylococcus epidermidis (including linezolid-resistant, LRSE) strains, but with no activity against Gram-neg. bacteria (Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa). Compound 44 showed strong bactericidal properties against susceptible and drug-resistant Gram-pos. bacteria. Depolarization of the bacterial cytoplasmic membrane induced by compound 44 suggests a dissipation of the bacterial membrane potential as its mechanism of antibacterial action. The high antimicrobial activity of compound 44, along with its selectivity over mammalian cells (lung MCR-5 and skin BJ fibroblast cell lines) and no hemolytic properties toward horse erythrocytes, proposes arylurea derivatives of aryloxy(1-phenylpropyl) alicyclic diamines for development of novel antibacterial agents.

Keywords: Arylurea derivatives ; Antibacterial properties ; Anti-MRSA activity ; Anti-VRE activity ; Anti-LRSE activity ; Depolarization of bacterial cell membrane

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Product Details of [ 404-71-7 ]

CAS No. :404-71-7 MDL No. :MFCD00002015
Formula : C7H4FNO Boiling Point : -
Linear Structure Formula :- InChI Key :RIKWVZGZRYDACA-UHFFFAOYSA-N
M.W : 137.11 Pubchem ID :123064
Synonyms :

Safety of [ 404-71-7 ]

Signal Word:Danger Class:6.1,3
Precautionary Statements:P261-P280-P305+P351+P338 UN#:3080
Hazard Statements:H225-H301-H312-H315-H319-H332-H335 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 404-71-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 404-71-7 ]

[ 404-71-7 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 20845-34-5 ]
  • [ 103-71-9 ]
  • [ 404-71-7 ]
  • (3-fluoro-phenyl)-carbamic acid 1-methyl-piperidin-2-ylmethyl ester [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 4953 - 4962
  • 2
  • [ 718632-46-3 ]
  • [ 404-71-7 ]
  • [ 1224175-18-1 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 1844 - 1853
  • 3
  • [ 63746-12-3 ]
  • [ 404-71-7 ]
  • C16H11FN2O4 [ No CAS ]
Reference： [1]Journal of Agricultural and Food Chemistry,2014,vol. 62,p. 11786 - 11796
  • 4
  • [ 17583-40-3 ]
  • [ 404-71-7 ]
  • 11-fluoro-5-methylbenzo[4,5]imidazo[1,2-c]quinazolin-6(5H)-one [ No CAS ]
  • 9-fluoro-5-methylbenzo[4,5]imidazo[1,2-c]quinazolin-6(5H)-one [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 587 - 590
    Angew. Chem.,2017,vol. 129,p. 602 - 605,4
  • 5
  • [ 17583-40-3 ]
  • [ 404-71-7 ]
  • 3,4-dihydro-3-(3-fluorophenyl)-4-imino-1-methylquinazolin-2(1H)-one [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 587 - 590
    Angew. Chem.,2017,vol. 129,p. 602 - 605,4
  • 6
  • [ 110223-15-9 ]
  • [ 404-71-7 ]
  • 1-(3-(benzyloxy)pyrazin-2-yl)-3-(3-fluorophenyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
76.8% In tetrahydrofuran;Inert atmosphere; Schlenk technique; Reflux; General procedure: 2-Amino-3-benzyloxypyridine or pyrazine derivative(2.5 mmol) was dissolved in dry THF (10 mL), isocyanate derivative(3.0 mmol) was added to the reaction mixture. The reaction wasrefluxed for 3-6 h. After cooling, the reaction mixture was evaporated and the residue was purified by solidification with cold methanol and filtered to give the target compounds.
Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 144,p. 529 - 543

Tags: 404-71-7 synthesis path| 404-71-7 SDS| 404-71-7 COA| 404-71-7 purity| 404-71-7 application| 404-71-7 NMR| 404-71-7 COA| 404-71-7 structure

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Chemistry
Organic Building Blocks
Fluorinated Building Blocks
fluorophenylisocyanate
Chemistry
Organic Building Blocks
Benzene Compounds
Chemistry
Organic Building Blocks
Isocyanates and Isothiocyanates

Technical Information

• Alkyl Halide Occurrence • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Friedel-Crafts Reaction • Hydrogenolysis of Benzyl Ether • Preparation of Alkylbenzene • Reactions of Benzene and Substituted Benzenes • Vilsmeier-Haack Reaction
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