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[ CAS No. 98-17-9 ] {[proInfo.proName]}

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Chemical Structure| 98-17-9
Chemical Structure| 98-17-9
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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 [ 98-17-9 ]

CAS No. :98-17-9 MDL No. :MFCD00002299
Formula : C7H5F3O Boiling Point : -
Linear Structure Formula :- InChI Key :UGEJOEBBMPOJMT-UHFFFAOYSA-N
M.W : 162.11 Pubchem ID :7376
Synonyms :

Calculated chemistry of [ 98-17-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 33.47
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : 2.95
Log Po/w (WLOGP) : 3.56
Log Po/w (MLOGP) : 2.57
Log Po/w (SILICOS-IT) : 2.35
Consensus Log Po/w : 2.59

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.04
Solubility : 0.147 mg/ml ; 0.000909 mol/l
Class : Soluble
Log S (Ali) : -3.04
Solubility : 0.149 mg/ml ; 0.000918 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.7
Solubility : 0.325 mg/ml ; 0.002 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 98-17-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P210-P261-P264-P271-P273-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501 UN#:N/A
Hazard Statements:H227-H315-H319-H335-H402 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 98-17-9 ]

* 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.

  • Upstream synthesis route of [ 98-17-9 ]
  • Downstream synthetic route of [ 98-17-9 ]

[ 98-17-9 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 98-08-8 ]
  • [ 64-18-6 ]
  • [ 20154-03-4 ]
  • [ 98-17-9 ]
  • [ 132537-44-1 ]
  • [ 132537-43-0 ]
  • [ 20154-03-4 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1990, vol. 109, # 12, p. 577 - 582
  • 2
  • [ 98-08-8 ]
  • [ 402-45-9 ]
  • [ 444-30-4 ]
  • [ 98-17-9 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 7, p. 2855 - 2861
[2] Catalysis Letters, 2015, vol. 145, # 4, p. 1014 - 1021
  • 3
  • [ 80783-62-6 ]
  • [ 108-95-2 ]
  • [ 402-45-9 ]
  • [ 444-30-4 ]
  • [ 98-17-9 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 38, p. 3929 - 3930
  • 4
  • [ 114436-00-9 ]
  • [ 444-30-4 ]
  • [ 98-17-9 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1994, # 3, p. 313 - 314
  • 5
  • [ 98-08-8 ]
  • [ 402-45-9 ]
  • [ 444-30-4 ]
  • [ 98-17-9 ]
  • [ 95-48-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1990, # 6, p. 937 - 942
  • 6
  • [ 98-17-9 ]
  • [ 40889-91-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 17, p. 5589 - 5599
  • 7
  • [ 98-17-9 ]
  • [ 53903-49-4 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 26, p. 5131 - 5133
  • 8
  • [ 98-17-9 ]
  • [ 328-90-5 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 15, p. 2911 - 2915
  • 9
  • [ 124-38-9 ]
  • [ 98-17-9 ]
  • [ 328-90-5 ]
Reference:
  • 10
  • [ 98-17-9 ]
  • [ 445-04-5 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 25, p. 8666 - 8680
[2] Journal of the Chemical Society, 1949, p. 3016,3019
  • 11
  • [ 83164-33-4 ]
  • [ 609-71-2 ]
  • [ 98-17-9 ]
  • [ 367-25-9 ]
  • [ 130191-66-1 ]
Reference: [1] Bulletin des Societes Chimiques Belges, 1990, vol. 99, # 5, p. 339 - 344
[2] Bulletin des Societes Chimiques Belges, 1990, vol. 99, # 5, p. 339 - 344
  • 12
  • [ 98-17-9 ]
  • [ 322-79-2 ]
Reference:
  • 13
  • [ 30082-44-1 ]
  • [ 98-17-9 ]
  • [ 28286-79-5 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 23, p. 6372 - 6376
[2] Journal of Organic Chemistry, 1993, vol. 58, # 23, p. 6372 - 6376
  • 14
  • [ 98-17-9 ]
  • [ 402-05-1 ]
YieldReaction ConditionsOperation in experiment
53% With bromine In carbon disulfide; hexane 2-bromo-5-trifluoromethylphenol
To a stirred solution of 61.65 gm (0.38 mole) 3-trifluoromethylphenol in 240 mL carbon disulfide were added 19.6 mL (0.38 mole) bromine dropwise.
The reaction mixture was stirred at room temperature for about 18 hours and was then partitioned between 200 mL dichloromethane and 100 mL water.
The organic phase was washed with 20 mL saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure.
The residue was subjected to silica gel chromatography, eluding with dichloromethane containing 40percent hexane.
Fractions containing product were combined and concentrated under reduced pressure to provide 48.8 gm (53percent) of the desired compound as a yellow oil.
Ion Spray MS: m/e=239, 241 (M+1)
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 1325
[2] Journal of Organic Chemistry, 1951, vol. 16, p. 586,606
[3] Patent: US6638936, 2003, B1,
  • 15
  • [ 98-17-9 ]
  • [ 454-82-0 ]
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 56, p. 108 - 119
  • 16
  • [ 98-17-9 ]
  • [ 320-49-0 ]
YieldReaction ConditionsOperation in experiment
30% at 20℃; To a solution of 3-trifluoromethylphenol (7.50 ml, 62 mmol), bromine(3.47 ml, 68 mmol) was added dropwise and the mixture was stirred at rt overnight. Ith was then poured onto water and extracted with dichloromethane. The combined organic layers were washed with 4percent sodium bicarbonate solution and brine. Solvent was removed to yield a crude product that was purified by column cromathography on silica gel using mixtures of hexane/ethyl acetate as mobil phase. 5.17g of the title compound (30percent yield).LRMS: m/z 241 (M-1)+ Retention time: 6.18 min (method B)1 H NMR (400 MHz, cdcl3) δ 7.53 (d, J = 8.6 Hz, 1 H), 7.19 (d, J = 2.9 Hz, 1 H), 6.87 (dd, J = 8.6, 2.9 Hz, 1 H), 5.98 (s, 1H).
Reference: [1] Patent: WO2011/35900, 2011, A1, . Location in patent: Page/Page column 80
[2] Patent: WO2004/35556, 2004, A1, . Location in patent: Page 94
[3] Patent: US5183934, 1993, A,
[4] Patent: EP423991, 1991, A2,
  • 17
  • [ 98-17-9 ]
  • [ 402-17-5 ]
YieldReaction ConditionsOperation in experiment
26.1% at 20 - 40℃; for 1 h; General procedure: An appropriate phenol (3) (150 mmol) was dissolved in glacial acetic acid (50 mL), and the solution was stirred and maintained at 40 °C. Then, a solution containing 11 mL of 65percent HNO3 and 30 mL of glacial acetic acid was added drop wise over 15 min. The mixture was stirred at r.t. for 45 min and poured into ice-water (400 mL). The aqueous mixture was extracted four times with CHCl3 (100 mL). Next, the organic phases were collected, dried with Na2SO4, evaporated and purified by column chromatography (4a, 4c, 4e) or crystallisation from ethanol (4b). Compound 4d was used for the next step without further purification [17].
Reference: [1] Organic Letters, 2008, vol. 10, # 14, p. 3025 - 3028
[2] European Journal of Medicinal Chemistry, 2012, vol. 56, p. 108 - 119
[3] Chemistry - A European Journal, 2011, vol. 17, # 33, p. 9076 - 9082
[4] Journal of Organic Chemistry, 1991, vol. 56, # 5, p. 1788 - 1800
[5] Patent: WO2006/5909, 2006, A1, . Location in patent: Page/Page column 52
[6] Patent: EP2274983, 2011, A1, . Location in patent: Page/Page column 123
[7] Patent: US2011/39843, 2011, A1, . Location in patent: Page/Page column 77
[8] Patent: WO2011/40629, 2011, A1, . Location in patent: Page/Page column 204
[9] Patent: WO2011/49220, 2011, A1, . Location in patent: Page/Page column 203
[10] Patent: WO2011/49221, 2011, A1, . Location in patent: Page/Page column 204
[11] Patent: WO2011/49223, 2011, A1, . Location in patent: Page/Page column 203
[12] Patent: WO2011/49222, 2011, A1, . Location in patent: Page/Page column 207
[13] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 22, p. 6842 - 6851
  • 18
  • [ 98-17-9 ]
  • [ 1643-19-2 ]
  • [ 124-63-0 ]
  • [ 91-00-9 ]
  • [ 106-89-8 ]
  • [ 90604-02-7 ]
Reference: [1] Patent: US5183902, 1993, A,
[2] Patent: US4956359, 1990, A,
[3] Patent: US5068231, 1991, A,
  • 19
  • [ 98-17-9 ]
  • [ 111141-02-7 ]
Reference: [1] Journal of Medicinal Chemistry, 1988, vol. 31, # 1, p. 230 - 243
  • 20
  • [ 98-17-9 ]
  • [ 111141-06-1 ]
  • [ 111141-02-7 ]
Reference: [1] Patent: US2012/302562, 2012, A1,
  • 21
  • [ 124-38-9 ]
  • [ 98-17-9 ]
  • [ 79427-88-6 ]
Reference: [1] European Journal of Organic Chemistry, 2001, # 15, p. 2911 - 2915
  • 22
  • [ 98-17-9 ]
  • [ 141483-15-0 ]
Reference: [1] Patent: CN104844399, 2016, B,
  • 23
  • [ 50-00-0 ]
  • [ 98-17-9 ]
  • [ 58914-34-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3057 - 3061
  • 24
  • [ 98-17-9 ]
  • [ 58914-34-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 12, p. 3162 - 3165
[2] Patent: US2013/90353, 2013, A1,
  • 25
  • [ 4684-94-0 ]
  • [ 98-17-9 ]
  • [ 137640-84-7 ]
YieldReaction ConditionsOperation in experiment
75% With potassium carbonate; copper(l) chloride In N,N-dimethyl-formamide at 140℃; for 6 h; To 500mL three-necked flask equipped with a thermometer, was added DMF (200ml), between sequentially added trifluoromethylphenol (0.26mol, 42.2g), potassium carbonate (0.266mol, 37.2g), 2-chloro-6-carboxy pyridine (0.2mol, 31.6g), cuprous chloride (1.0 g of), heated to 140 deg.] C, the reaction 6.0H, cooled to room temperature, the reaction solution was poured into 600ml of ice water, pH = 3 adjusted with concentrated brine, and the precipitated solid was pumped was filtered off, washed with water, dried to obtain a white solid, yield: 75percent
Reference: [1] Patent: CN108530351, 2018, A, . Location in patent: Paragraph 0011; 0026; 0028
  • 26
  • [ 98-17-9 ]
  • [ 137640-84-7 ]
Reference: [1] Patent: CN107382847, 2017, A,
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