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[ CAS No. 1195-45-5 ] {[proInfo.proName]}

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Chemical Structure| 1195-45-5
Chemical Structure| 1195-45-5
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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 [ 1195-45-5 ]

CAS No. :1195-45-5 MDL No. :MFCD00002023
Formula : C7H4FNO Boiling Point : -
Linear Structure Formula :- InChI Key :DSVGFKBFFICWLZ-UHFFFAOYSA-N
M.W : 137.11 Pubchem ID :70955
Synonyms :

Safety of [ 1195-45-5 ]

Signal Word:Danger Class:3,6.1
Precautionary Statements:P210-P233-P240-P241-P242-P243-P261-P264-P270-P271-P272-P280-P284-P301+P312+P330-P303+P361+P353-P304+P340+P312-P305+P351+P338-P333+P313-P337+P313-P342+P311-P370+P378-P403+P235-P501 UN#:2478
Hazard Statements:H226-H302+H312+H332-H317-H319-H334 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1195-45-5 ]

* 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 [ 1195-45-5 ]

[ 1195-45-5 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 117011-70-8 ]
  • [ 1195-45-5 ]
  • [ 121809-72-1 ]
  • 2
  • [ 198211-38-0 ]
  • [ 1195-45-5 ]
  • [ 888493-42-3 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; for 3h; To a solution of the compound (Example 3, step b) (1.5 g, 7.75 mmol) in dichloromethane (20 ml), was added 4-fluorophenyl isocyanate (1.24 g, 9.09 mmol) and stirred for 3 hours. The reaction mixture was poured into water, extracted with dichloromethane and washed with water. The dichloromethane layer was dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. The residue thus obtained was purified by column chromatography using methanol in dichloromethane (1:49) solvent mixture as eluent to furnish the title compound. Yield = 2.1 g.
In dichloromethane; at 0℃; for 3h; Example 3; Synthesis of 6-amino-3-azabicyclo[3.1.0]hexane-3-N-(4-fluorophenyl)carboxamide (pTSA salt)Step a: Synthesis of tert-butyl (3-[(4-fluorophenyl)amino]carbonyl}-3-azabicyclo[3.1.0]hex-6-yl)carbamateTo a solution of tert-butyl 3-azabicyclo[3.1.0]hex-6-ylcarbamate (0.500 g, 2.50 mmol) in dichloromethane (10.0 mL) at 0 C., was added dropwise a solution of 4-fluorophenyl isocyanate (0.34 mL, 3.0 mmol) in dichloromethane (5.0 mL) and stirred at 0 C. for about 3 hours. The reaction mixture was partitioned between water (10.0 mL) and dichloromethane (20.0 mL). The organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to yield the title product, which was used directly in the next step.
  • 3
  • [ 214147-48-5 ]
  • [ 1195-45-5 ]
  • [ 283167-10-2 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In dichloromethane; EXAMPLE 10 To a suspension of <strong>[214147-48-5]1-acetyl-4-aminopiperidine hydrochloride</strong> (536 mg) in dichloromethane (5 ml) were added 4-fluorophenyl isocyanate (375 mul) and diisopropylethylamine (575 mul) at ambient temperature. After stirring for 3 hours, the reaction mixture was diluted with dichloromethane. An organic phase was separated and an aqueous phase was extracted with dichloromethane. A combined organic phase was dried over magnesium sulfate and the solvents were removed under reduced pressure. After crystallization from diisopropyl ether and n-hexane, N-(1-acetylpiperidin-4-yl)-N'-(4-fluorophenyl)urea (448 mg) was obtained. NMR (DMSO-d6, delta): 1.1-1.5 (2H, m), 1.80 (2H, distorted t, J=10 Hz), 2.00 (3H, s), 2.77 (1H, br d, J=10.8 Hz), 3.14 (1H, br d, J=11.1 Hz), 3.5-3.9 (2H, m), 4.16 (1H, br d, J=13.2 Hz), 6.15 (1H, d, J=7.6 Hz), 7.05 (2H, t, J=8.9 Hz), 7.40 (2H, dd, J=5.0, 9.2 Hz), 8.37 (1H, s)
  • 4
  • [ 150008-24-5 ]
  • [ 1195-45-5 ]
  • [ 1092464-56-6 ]
YieldReaction ConditionsOperation in experiment
96% With triethylamine; In tetrahydrofuran; at 0℃; for 4.16667h; A solution of 4-fluorophenylisocyanate (775 mg, 5.65 mmol) in tetrahydrofuran (20 ml) was added to a solution of tert-butyl 4-(hydroxyimino)piperidine-1- carboxylate (1.00 g, 4.67 mmol) and triethylamine (0.783 ml, 5.65 mmol) in tetrahydrofuran (30 ml) at 0C over 10 minutes and stirred at 0C for 4 hours. The mixture was concentrated in vacuo and the residual solid was recrystallized from ethyl acetate/n-hexane to give tert- butyl 4-(4-fluorophenylcarbamoyloxyimino)piperidine-1-carboxylate (1.57 g, 96 %) as a white solid.
  • 5
  • [ 1195-45-5 ]
  • [ 157869-15-3 ]
  • [ 1096541-31-9 ]
  • 6
  • [ 3236-48-4 ]
  • [ 1195-45-5 ]
  • C15H20FNO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; In dichloromethane; at 20℃; Example 1.65: Preparation of 2-(((lr,4r)-4-(((4-Chlorophenyl)(4- fluorophenyl)carbamoyloxy)methyl)cyclohexyl)methoxy)acetic Acid (Compound 76).; Step A: Preparation of Methyl 4-Fluoro-2-((lr,4r)-4- (hydroxymethyl)cyclohexyl)phenylcarbamate.; 4-Fluorophenyl isocyanate (4.75 g, 34.7 mmol), (lr,4r)-cyclohexane-l,4-diyldimethanol (5.0 g, 34.7 mmol), and pyridine (3.93 mL, 48.5 mmol) were dissolved in CH2Cl2 (30 mL). The reaction mixture was stirred at room temperature overnight. After removal of the solvent, the residue was purified by silica gel column chromatography to yield the title compound as a white solid (4.92 g). LCMS m/z = 282.4 [M+H]+; 1H NMR (400 MHz, DMSCwZ6) delta ppm 0.81-1.07 (m, 4H), 1.25-1.38 (m, IH), 1.49-1.64 (m, IH), 1.72-1.82 (m, 4H), 3.19-3.24 (m, 2H), 3.89 (d, J = 6.57 Hz, 2H), 4.34 (t, J= 5.31 Hz, IH), 7.06-7.15 (m, 2H), 7.46 (dd, J= 8.97, 4.93 Hz, 2H), 9.61 (s, IH).
  • 7
  • [ 1197159-91-3 ]
  • [ 1195-45-5 ]
  • [ 1197159-96-8 ]
  • 8
  • [ 30235-28-0 ]
  • [ 1195-45-5 ]
  • [ 1342277-11-5 ]
YieldReaction ConditionsOperation in experiment
28% In N,N-dimethyl-formamide; at 150℃; for 0.333333h;Biotage microwave; COMPOUND 6cl-(4-Fluorophenyl)-3-(4-(pyridin-4-yl)thiazol-2-yl)urea. A mixture of 3a (0.095 g, 0.536 mmol), 4-fluorophenyl isocyanate (0.147 g, 1.073 mmol) in anhydrous DMF (0.6 ml), was stirred in a Biotage microwave at 150 C for 20 min After cooling to room temperature, the solvent was removed under reduced pressure and chromatography on silica gel performed using the FlashMaster 3 purification station afforded 6c as an off white solid (0.047 g, 0.149 mmol, 28%). 1H NMR (400 MHz, DMSO-d6) delta 10.82 (s, 1H), 8.96 (s, 1H), 8.59 (d, J= 6.0 Hz, 2H), 7.91 (s, 1H), 7.81 (d, J= 6.0 Hz, 2H), 7.50-7.46 (m, 2H), 7.16 (t, J = 8.8 Hz, 2H); HRMS (ESI +ve) m/z calculated for Ci5Hi2N4FOS (M + H)+ 315.0710, found 315.0713.
  • 9
  • [ 773-76-2 ]
  • [ 1195-45-5 ]
  • [ 1221161-40-5 ]
  • 10
  • [ 6296-99-7 ]
  • [ 1195-45-5 ]
  • [ 1437323-24-4 ]
YieldReaction ConditionsOperation in experiment
85% With N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 100℃; for 6.0h; a) 2-Aminomethylene-malonic acid diethyl ester (16.7 g, 89.2 mmol) and 4- fluorophenyl isocyanate (10.6 mL, 93.7 mmol) in 1 ,2-dichloroethane (25 mL, 320 mmol) was added N,N-diisopropylethylamine (17.1 mL, 98.1 mmol) and heated at 100 C for 6h. The mixture was cooled on an ice bath and the solid collected and washed with ether to give the urea (24.5 g, 85%). mp = 198-200 C; LCMS m/z = 347 (M + 23); 1H NMR (DMSO) ?: 10.57 (d, 1H, J = 12.3 Hz), 10.41 (s, 1H), J = 12.45 Hz), 8.45 (d, 1H, J = 12.5 Hz), 7.48-7.53 (m, 2H), 7.16-7.21 (m, 2H), 4.24 (q, 2H, J = 7 Hz), 4.15 (q, 2H, J = 7 Hz), 1.22-1.28 (m, 6H).
85% With N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 100℃; for 6.0h; a) 2-Aminomethylene-malonic acid diethyl ester (16.7 g, 89.2 mmol) and 4- fluorophenyl isocyanate (10.6 mL, 93.7 mmol) in 1,2-dichloroethane (25 mL, 320 mmol) was added N,N-diisopropylethylamine (17.1 mL, 98.1 mmol) and heated at 100 C for 6h. The mixture was cooled on an ice bath and the solid collected and washed with ether to give the urea (24.5 g, 85%). mp = 198-200 C; LCMS m/z = 347 (M + 23); 1H NMR (DMSO) delta: 10.57 (d, 1H, J = 12.3 Hz), 10.41 (s, 1H), J = 12.45 Hz), 8.45 (d, 1H, J = 12.5 Hz), 7.48-7.53 (m, 2H), 7.16-7.21 (m, 2H), 4.24 30 (q, 2H, J = 7 Hz), 4.15 (q, 2H, J = 7 Hz), 1.22-1.28 (m, 6H).
1.01 g With N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 100℃; for 16.0h; Diethyl 2-(aminomethylene)malonate (1.5 g, 8.0 . mmol, CombiBlocks) and 1- fluoro-4-isocyanatobenzene (0.957 ml, 8.41 mmol) were suspended in DCE (2.67 ml) at room temperature. DIPEA (1.539 ml, 8.81 mmol) was added followed by the dropwise addition of l-fluoro-4-isocyanatobenzene (0.957 ml, 8.41 mmol). The reaction mixture was heated to 100 C and stirred for 16 hr. The partially solidified reaction mixture was cooled to room temperature and diluted with 10 mL of 50% Et20-CH2Cl2. The remaining precipitate was filtered to afford diethyl 2-((3-(4-fluorophenyl)ureido) methylenelma.onate as a cream solid (1.01 g) 1H NMR (400 MHz, DMSO-d6) d 10.72 - 10.32 (m, 21 .}. 8 47 (br d,.1 5.7 Hz, 1H), 7.61 - 7.43 (m, 2H), 7.26 - 6 99 (m, 2H), 4.24 (q, 1=7.1Hz, 21 i s. 4.15 (q, 1=7.1Hz, 2H), 1.26 (dt, j 12.0. 7.1Hz, 6H); LC/MS (M+H) 325.2; LC RT = 0.92 min (Column: BEH C18 2.1 x 50mm; Mobile Phase A: water with 0.05% TEA; Mobile Phase B: acetonitrile with 0.05% TFA; Temperature: 50 C; Gradient: 2-98% B over 1.7 min; Flow: 0.8 mL/min)
  • 11
  • [ 604-50-2 ]
  • [ 1195-45-5 ]
  • [ 1629888-36-3 ]
YieldReaction ConditionsOperation in experiment
81% General procedure: A solution of <strong>[604-50-2]1-methylquinazoline-2,4(1H,3H)-dione</strong>2 (0.1 mmol) in dimethylformamide (1 mL) was taken andcooled to 0-5 oC in an ice bath. Triethylamine (0.12 mmol)was added to cold reaction mixture and stirred for 30 min.Different substituted isocyanates (0.1 mmol) were added tothe mixture and allowed to stir at room temperature for 4 h.The progress of the reaction was monitored by TLC. Uponcompletion, the reaction mixture was diluted with water andextracted with ethyl acetate. The organic layer was washedwith water and dried over anhydrous sodium sulfate. Thefiltrate was concentrated in vaccuo to get the crude productwhich was purified by column chromatography over silicagel (60-120 mesh) using hexane: ethyl acetate (9:1) as eluentto afford the thiourea in 80-87% yields.
  • 12
  • [ 63746-12-3 ]
  • [ 1195-45-5 ]
  • C16H11FN2O4 [ No CAS ]
  • 13
  • [ 1195-45-5 ]
  • [ 302348-51-2 ]
  • C20H23BFNO4 [ No CAS ]
  • 14
  • [ 1195-45-5 ]
  • [ 98-32-8 ]
  • 3-(3-(4-fluorophenyl)ureido)-4-hydroxybenzenesulfonamide [ No CAS ]
  • 15
  • [ 3236-48-4 ]
  • [ 1195-45-5 ]
  • [ 1187856-96-7 ]
  • 16
  • [ 21911-84-2 ]
  • [ 1195-45-5 ]
  • C17H15FN2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With silver (II) carbonate; palladium diacetate; In 1,2-dichloro-ethane; at 20 - 120℃; Add to round bottom flaskMethyl 3- (phenylamino) propionate (1 equivalent),Palladium acetate (2mol%),Silver carbonate (2 equivalents) and dichloroethane (4 mL) were added, and after stirring, 4-fluorophenyl isocyanate (1.5 equivalents) was added at room temperature.The reaction solution was heated at 120 C. After the reaction was monitored by TLC, the celite was filtered.The filtrate was concentrated by rotary evaporation, and the residue was purified by column chromatography (PE / EA = 1/2).To obtain intermediate 1,The yield was 75%.
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