[ CAS No. 372-20-3 ] {[proInfo.proName]}

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Quality Control of [ 372-20-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 372-20-3 ]

SDS Specification

Alternatived Products of [ 372-20-3 ]

Product Citations

Design and synthesis of novel arylurea derivatives of aryloxy (1-phenylpropyl) alicyclic diamines with antimicrobial activity against multidrug-resistant Gram-positive bacteria

Canale, Vittorio ; Czekajewska, Joanna ; Klesiewicz, Karolina , et al. Eur. J. Med. Chem.,2023,251,115224. DOI: 10.1016/j.ejmech.2023.115224 PubMed ID: 36958177

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

Purchased from AmBeed: 122536-76-9 ; 936-59-4 ; 135632-53-0 ; 404-71-7 ; 73874-95-0 ; 372-20-3 ; 98-17-9 ; 402-45-9 ; 57260-71-6 ; 122536-77-0 ; 444-30-4 ; 165800-03-3 ; 150-19-6 ; 1195-45-5 ; 2909-38-8 ; 165800-03-3 ...More

Product Details of [ 372-20-3 ]

CAS No. :	372-20-3	MDL No. :	MFCD00002254
Formula :	C₆H₅FO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SJTBRFHBXDZMPS-UHFFFAOYSA-N
M.W :	112.10	Pubchem ID :	9743
Synonyms :

Calculated chemistry of [ 372-20-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	28.42
TPSA :	20.23 ?2

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) :	-5.61 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.37
Log Po/w (XLOGP3) :	1.93
Log Po/w (WLOGP) :	1.95
Log Po/w (MLOGP) :	1.9
Log Po/w (SILICOS-IT) :	1.84
Consensus Log Po/w :	1.8

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.31
Solubility :	0.554 mg/ml ; 0.00494 mol/l
Class :	Soluble
Log S (Ali) :	-1.98
Solubility :	1.18 mg/ml ; 0.0105 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.04
Solubility :	1.02 mg/ml ; 0.0091 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 372-20-3 ]

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P280-P301+P310-P305+P351+P338	UN#:	2922
Hazard Statements:	H227-H301+H311+H331-H314-H412	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 372-20-3 ]

* 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 [ 372-20-3 ]
Downstream synthetic route of [ 372-20-3 ]

[ 372-20-3 ] Synthesis Path-Upstream 1~6

1
[ 372-20-3 ]
[ 79-11-8 ]
[ 404-98-8 ]

Reference： [1] Journal of the American Chemical Society, 1943, vol. 65, p. 1555
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 14, p. 4336 - 4347
[3] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 1, p. 183 - 187

2
[ 372-20-3 ]
[ 105-36-2 ]
[ 404-98-8 ]

Reference： [1] Patent: WO2014/100730, 2014, A1, . Location in patent: Paragraph 00262
[2] Patent: US2019/83482, 2019, A1, . Location in patent: Paragraph 0236-0237

3
[ 372-20-3 ]
[ 96-32-2 ]
[ 404-98-8 ]

Reference： [1] Tetrahedron Letters, 2015, vol. 56, # 29, p. 4383 - 4387

4
[ 372-20-3 ]
[ 404-98-8 ]

Reference： [1] Journal of Fluorine Chemistry, 2006, vol. 127, # 2, p. 291 - 295
[2] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 1, p. 173 - 179
[3] Bulletin of the Korean Chemical Society, 2015, vol. 36, # 10, p. 2549 - 2552

5
[ 372-20-3 ]
[ 107-30-2 ]
[ 126940-10-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: With N-ethyl-N,N-diisopropylamine In dichloromethane at -10℃; for 0.25 h; Stage #2: at -10 - 20℃; for 22.08 h;	A solution of 100 gm (0.892 mol) 3-fluorophenol in 800 ML dichloromethane was cooled to -10°C. To this solution were added 155 gm (1.20 mol) diisopropylethylamine dropwise over 15 minutes.. Residual diisopropylethylamine in the addition funnel was rinsed into the reaction mixture with 100 ML dichloromethane.. To the resulting solution were added 100 gm (1.24 mol) chloromethyl methyl ether over 5 minutes, resulting an exotherm from -10°C to 2°C. The reaction mixture was allowed to warm to room temperature.. After 22 hours the reaction mixture was quenched with 500 ML water.. The organic phase was washed with 500 ML 2M aqueous sodium bisulfate followed by 300 ML 1M sodium hydroxide.. The remaining organics were dried over magnesium sulfate and concentrated under reduced pressure to provide 130 gm of a yellow oil.. The oil was distilled (kugelrohr, 80°C, 0.1 torr) to provide 126 gm (91percent) of the desired compound as a colorless oil.

Reference： [1] ChemBioChem, 2015, vol. 16, # 17, p. 2445 - 2450
[2] Patent: EP1204660, 2004, B1, . Location in patent: Page 19
[3] European Journal of Organic Chemistry, 2001, # 15, p. 2911 - 2915
[4] Tetrahedron Letters, 2001, vol. 42, # 37, p. 6499 - 6502
[5] ChemMedChem, 2017, vol. 12, # 1, p. 23 - 27

6
[ 109-87-5 ]
[ 372-20-3 ]
[ 126940-10-1 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1293 - 1298

[ 372-20-3 ] Synthesis Path-Downstream 1~10

1
[ 13195-50-1 ]
[ 372-20-3 ]
[ 190966-71-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 779 - 786

2
[ 940890-90-4 ]
[ 372-20-3 ]
C₁₆H₂₂FNO₃ [ No CAS ]
C₁₆H₂₂FNO₃ [ No CAS ]
[ 85838-94-4 ]

Reference： [1]Synthetic Communications,2008,vol. 38,p. 517 - 524

3
[ 940890-90-4 ]
[ 372-20-3 ]
(R)-3-(3-fluoro-phenoxy)-piperidine [ No CAS ]
(S)-3-(3-fluoro-phenoxy)-piperidine [ No CAS ]

Reference： [1]Synthetic Communications,2008,vol. 38,p. 517 - 524

4
[ 372-20-3 ]
[ 363-52-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 6217 - 6229

5
[ 372-20-3 ]
[ 84851-56-9 ]
methyl 4-(1-(3-fluorophenoxy)ethyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 12h;	Methyl 4-(l-(3-fluorophenoxy)ethyl)benzoate. To a solution of methyl 4-(l- hydroxyethyl)benzoate (0.9 g, 5 mmol), 3-fluorophenol (627 mg, 5.6 mmol), triphenylphosphine (2.2 g, 8.4 mmol) in tetrahydrofuran (30 mL) was added diisopropyl azodicarboxylate (1.7 g, 8.4 mmol) at 0C. The mixture was stirred at 20C for 12 hours. Water (15 mL) was added to the mixture and then extracted with ethyl acetate (35 mL x 3). The combined organic phase was dried by sodium sulfate, and then filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 5:1) to give methyl 4-(l-(3-fluorophenoxy)ethyl)benzoate (400 mg, 29%).
29%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 12h;	To a solution of methyl 4-(1-hydroxyethyl)benzoate (0.9 g, 5 mmol), 3-fluorophenol (627 mg, 5.6 mmol), triphenylphosphine (2.2 g, 8.4 mmol) in tetrahydrofuran (30 mL) was added diisopropyl azodicarboxylate (1.7 g, 8.4 mmol) at 0 C. The mixture was stirred at 20 C. for 12 hours. Water (15 mL) was added to the mixture and then extracted with ethyl acetate (35 mL×3). The combined organic phase was dried by sodium sulfate, and then filtered. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to give methyl 4-(1-(3-fluorophenoxy)ethyl)benzoate (400 mg, 29%).

Reference： [1]Patent: WO2013/75083,2013,A1 .Location in patent: Paragraph 00296; 00297; 00438; 00439
[2]Patent: US9206128,2015,B2 .Location in patent: Page/Page column 151; 152; 205; 206

6
[ 372-20-3 ]
[ 127-17-3 ]
[ 7423-96-3 ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 926 - 935

7
[ 372-20-3 ]
[ 1435-54-7 ]
1-bromo-2-fluoro-3-(3-fluorophenoxy)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.5%		3-fluorophenol (0.107 mL, 1.18 mmol) and KOH (66 mg, 1.18 mmol) were stirred at 50 °C for 30 min before the addition of l,3-dibromo-2-fluorobenzene (300 mg, 1.18 mmol) and Cu powder (75 mg, 1.18 mmol). The reaction mixture was heated to 100 °C overnight. The crude material was purified by FC on silica gel (eluent: Cy), giving l-bromo-2-fluoro-3-(3-fluorophenoxy)benzene (P7, 12 mg, y= 3.5percent) as oil.

Reference： [1]Patent: WO2016/42453,2016,A1 .Location in patent: Page/Page column 54

8
[ 372-20-3 ]
[ 1077-01-6 ]

Reference： [1]Journal of Fluorine Chemistry,2017,vol. 203,p. 130 - 135

9
[ 372-20-3 ]
[ 111141-00-5 ]

Reference： [1]Patent: WO2008/151927,2008,A2

10
[ 372-20-3 ]
[ 522-17-8 ]

Reference： [1]Synthesis,2019,vol. 51,p. 1139 - 1156

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Isomers

Technical Information

? Acidity of Phenols ? Alkyl Halide Occurrence ? Chan-Lam Coupling Reaction ? Electrophilic Substitution of the Phenol Aromatic Ring ? Etherification Reaction of Phenolic Hydroxyl Group ? Halogenation of Phenols ? Oxidation of Phenols ? Pechmann Coumarin Synthesis ? Preparation of Aldehydes and Ketones ? Reactions of Benzene and Substituted Benzenes ? Reimer-Tiemann Reaction

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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 372-20-3 ] {[proInfo.proName]}

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Fluorinated Building Blocks

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