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[ CAS No. 402-45-9 ] {[proInfo.proName]}

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Chemical Structure| 402-45-9
Chemical Structure| 402-45-9
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Product Citations

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Anushree Mondal ; Pronay Roy ; Jaclyn Carrannatto , et al. DOI: PubMed ID:

Abstract: The prenylated-flavin mononucleotide-dependent decarboxylases (also known as UbiD-like enzymes) are the most recently discovered family of decarboxylases. The modified flavin facilitates the decarboxylation of unsaturated carboxylic acids through a novel mechanism involving 1,3-dipolar cyclo-addition chemistry. UbiD-like enzymes have attracted considerable interest for biocatalysis applications due to their ability to catalyse (de)carboxylation reactions on a broad range of aromatic substrates at otherwise unreactive carbon centres. There are now ∼35[thin space (1/6-em)]000 protein sequences annotated as hypothetical UbiD-like enzymes. Sequence similarity network analyses of the UbiD protein family suggests that there are likely dozens of distinct decarboxylase enzymes represented within this family. Furthermore, many of the enzymes so far characterized can decarboxylate a broad range of substrates. Here we describe a strategy to identify potential substrates of UbiD-like enzymes based on detecting enzyme-catalysed solvent deuterium exchange into potential substrates. Using ferulic acid decarboxylase (FDC) as a model system, we tested a diverse range of aromatic and heterocyclic molecules for their ability to undergo enzyme-catalysed H/D exchange in deuterated buffer. We found that FDC catalyses H/D exchange, albeit at generally very low levels, into a wide range of small, aromatic molecules that have little resemblance to its physiological substrate. In contrast, the sub-set of aromatic carboxylic acids that are substrates for FDC-catalysed decarboxylation is much smaller. We discuss the implications of these findings for screening uncharacterized UbiD-like enzymes for novel (de)carboxylase activity.

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ;

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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Bygd, Madison D ;

Abstract: Polyfluorinated compounds have become a popular topic in recent years for their widespread use and prominence as a pollutant in our environment. Their use in thousands of commercial products and chemicals has raised concern due to their resistance to degradation, coining them the “forever chemicals.” To better understand how these compounds are degraded and find microorganisms capable of remediation, biological degradative mechanisms were investigated. It was shown that 2,2-difluoro-1,3-benzodioxole, a common fluorinated moiety found in agricultural chemicals and pharmaceuticals, can be degraded and defluorinated by Pseudomonas putida F1. To better detect and screen for additional microbial related defluorination mechanisms, a color screen using alizarin and lanthanum was developed for use in biological contexts. Compatible with various media and solvents, this assay uncovered an additional 23 defluorination reactions initiated by P. putida F1. Further screening was continued with the E. coli ASKA library in which an additional novel defluorination reaction was found to be catalyzed by the enzyme PgpB. The color screen proved to be a highly effective and efficient method for detecting fluoride release by biological means in a high-throughput manner. The data presented in this thesis show many previously undocumented defluorination reactions and outline an efficient and effective method for detecting microbial based bioremediation of polyfluorinated chemicals.

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Product Details of [ 402-45-9 ]

CAS No. :402-45-9 MDL No. :MFCD00002363
Formula : C7H5F3O Boiling Point : -
Linear Structure Formula :- InChI Key :BAYGVMXZJBFEMB-UHFFFAOYSA-N
M.W : 162.11 Pubchem ID :67874
Synonyms :

Calculated chemistry of [ 402-45-9 ]      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) : -5.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : 2.82
Log Po/w (WLOGP) : 3.56
Log Po/w (MLOGP) : 2.57
Log Po/w (SILICOS-IT) : 2.35
Consensus Log Po/w : 2.56

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.96
Solubility : 0.178 mg/ml ; 0.0011 mol/l
Class : Soluble
Log S (Ali) : -2.9
Solubility : 0.203 mg/ml ; 0.00125 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 [ 402-45-9 ]

Signal Word:Danger Class:4.1,6.1
Precautionary Statements:P210-P240-P241-P261-P264-P270-P271-P280-P301+P310+P330-P302+P352-P304+P340+P312-P305+P351+P338+P310-P332+P313-P370+P378-P403+P233-P405-P501 UN#:2926
Hazard Statements:H228-H301-H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 402-45-9 ]

* 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.

  • Downstream synthetic route of [ 402-45-9 ]

[ 402-45-9 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 16222-44-9 ]
  • [ 402-45-9 ]
  • 2
  • [ 402-45-9 ]
  • [ 3337-62-0 ]
  • 3
  • [ 402-45-9 ]
  • [ 3513-81-3 ]
  • [ 849442-18-8 ]
YieldReaction ConditionsOperation in experiment
50% With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at 0 - 20℃; 2- (4-TRIFLUOROMETHYI-PHENOXYMETHYL)-PROP-2-EN-1-OL; To a mixture of 4-TRIFLUOROMETHYLPHENOL (49.0 g, 302 mmol), 2-methylene- 1, 3-PROPANEDIOL (40.0 g, 454 MMOL), and diisopropyl azodicarboxylate (67.4 g, 333 MMOL) in CH2C12 (400 mL) at 0°C was charged with a solution of TRIPHENYLPHOSPHINE (87.2 g, 333 MMOL) in CH2Cl2 (400 mL) dropwise. After the mixture was stirred at 0°C and then allowed to warm up to room temperature overnight, CH2C12 was evaporated under reduced pressure. To the residue was added ET20 and hexane, and the mixture was cooled to 0°C. The precipitated solid was filtered, and the filtrate was concentrated and column chromatographed (EtOAc/hexane: 1/4) to give 35.2 g (50percent) of 2-A ;'H NMR (300 MHz, CDCl3) 8 7.55 (d, J = 8. 6 HZ, 2 H), 6.99 (d, J = 8. 6 HZ, 2 H), 5.33 (d, J = 0. 9 HZ, 1 H), 5.29 (d, J = 0. 9 Hz, 1 H), 4.65 (s, 2 H), 4.27 (d, J = 6. 0 Hz, 2 H).
50% With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at 0 - 20℃; 2-(4-Trifluoromethyl-phenoxymethyl)-prop-2-en-1-ol To a mixture of 4-trifluoromethylphenol (49.0 g, 302 mmol), <strong>[3513-81-3]2-methylene-1,3-propanediol</strong> (40.0 g, 454 mmol), and diisopropyl azodicarboxylate (67.4 g, 333 mmol) in CH2Cl2 (400 mL) at 0° C. was charged with a solution of triphenylphosphine (87.2 g, 333 mmol) in CH2Cl2 (400 mL) dropwise. After the mixture was stirred at 0° C. and then allowed to warm up to room temperature overnight, CH2Cl2 was evaporated under reduced pressure. To the residue was added Et2O and hexane, and the mixture was cooled to 0° C. The precipitated solid was filtered, and the filtrate was concentrated and column chromatographed (EtOAc/hexane: 1/4) to give 35.2 g (50percent) of 2-A; 1H NMR (300 MHz, CDCl3) delta 7.55 (d, J=8.6 Hz, 2 H), 6.99 (d, J=8.6 Hz, 2 H), 5.33 (d, J=0.9 Hz, 1 H), 5.29 (d, J=0.9 Hz, 1 H), 4.65 (s, 2 H), 4.27 (d, J=6.0 Hz, 2 H).
  • 4
  • [ 17641-08-6 ]
  • [ 402-45-9 ]
  • [ 1210031-82-5 ]
  • 5
  • [ 402-45-9 ]
  • [ 116457-91-1 ]
  • [ 1393477-17-2 ]
YieldReaction ConditionsOperation in experiment
50% Step 3[00247] To a solution of triphenylphosphine (3 eq) in dry THF under Argon was added diethylazodicarboxylate (3 eq) dropwise. The reaction mixture was stirred at room temperature for 15 minutes before adding a solution of 4-(trifluoromethyl)phenol (3eq in dry THF) dropwise. The reaction mixture was stirred at room temperature for 1 hour before adding (R)-methyl 3-hydroxy-2-(tritylamino)propanoate (LXXXIX) in dry THF in one portion. The reaction mixture was stirred at room temperature ovenight. The mixture was concentrated to dryness, treated with hexane and filtered. The residue was concentrated to dryness and purified by silica flash chromatography (EtOAc/hexane = 1 :5). Pure (R)-methyl 3-(4- (trifluoromethyl)phenoxy)-2-(tritylamino)propanoate (XC) was obtained as an off-white solid (50% yield).
  • 7
  • [ 402-45-9 ]
  • [ 1147557-97-8 ]
  • C18H22F3NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 0 - 20℃; for 16h;Inert atmosphere; Preparation of intermediate BP DIAD ( 1.40 g, 6.92 mmol) in toluene ( 10 mL) was added to a solution of tert-butyl 6-hydroxy-2-azaspiro[3.3]lieptane-2-carboxyl.ate (CAS [1147557-97-8], 1.2 g, 5.63 mmol), 4-(trifluoromethyl)phenol (CAS [402-45-9], 1.10 g, 6.75 mmol), and triphenylphosphine (2.31 g, 8.80 mmol) in toluene (40 mL) at 0 °C under N2 flow. The mixture was stirred overnight at room temperature. The mixture was concentrated. The crude product was purified by column chromatography over silica gel (petroleum ether/ethyl acetate from 1/0 to 3/1). The desired fraction was collected and concentrated to give intermediate BP, 2 g, 99percent.
With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 0 - 20℃; for 16h;Inert atmosphere; DIAD ( l .40 g, 6.92 mmol) in toluene ( 10 mL) was added to a solution of tert-butyl (0207) 6-hydroxy-2-azaspiro[3.3]heptane-2-carboxyl.ate (CAS [1147557-97-8], 1.2 g, (0208) 5.63 mmol), 4-(trifluoromethyl)phenol (CAS [402-45-9], 1.10 g, 6.75 mmol), and (0209) triphenylphosphine (2.31 g, 8.80 mmol) in toluene (40 mL) at 0 °C under N2 flow. The mixture was stirred overnight at room temperature. The mixture was concentrated. The crude product was purified by column chromatography over silica gel (petroleum (0210) ether/ethyl acetate from 1/0 to 3/1). The desired fraction was collected and concentrated to give intermediate E, 2 g, 99percent.
  • 8
  • [ 327056-62-2 ]
  • [ 402-45-9 ]
  • 5-[4-(trifluoromethyl)phenoxy]pyridine-2-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate; In dimethyl sulfoxide; at 110℃; for 1h; 2-Cyano-5-fluoropyridine (3.54 g; 28.99 mmol), 4-trifluoromethyl-phenol (4.70 g; 28.99 mmol) and potassium carbonate (6.01 g; 43.49 mmol) are stirred in DMSO (150 mL) at 1 10C for 1 hour. The reaction mixture is diluted with water and extracted with EtOAc. The organic layer is washed with water, separated, dried over Na2S04, filtered and concentrated under reduced pressure. (1126) Yield: quantitative ESI-MS: m/z = 265 [M+H]+ Rt(HPLC): 1 .03 min (method 10)
92% With potassium carbonate; In N,N-dimethyl acetamide; at 100℃; for 6h; Step A: A mixture of 4-(trifluoromethyl)phenol (2.9 g,18 mmol), <strong>[327056-62-2]2-cyano-5-fluoropyridine</strong> (2.0 g, 9.0 mmol), K2CO3(2.7 g, 20 mmol) and DMA (20 mL) was stirred at 100 C for 6 h.After cooling to room temperature, the reaction mixture wasdiluted with water and extracted with AcOEt. The organic layerwas washed with brine, dried over Na2SO4 and concentrated invacuo. The resulting residue was purified by silica gel chromatography(hexane-AcOEt) to give 5-[4-(trifluoromethyl)phenoxy]pyridine-2-carbonitrile (4.0 g, 92%) as a colorless solid. 1H NMR (CDCl3)d: 8.50 (1H, d, J = 2.4 Hz), 7.71-7.69 (3H, m), 7.35 (1H, dd, J = 8.8,2.9 Hz), 7.19 (2H, d, J = 8.8 Hz). MS (ESI+) m/z: 264 (M+H)+.
  • 9
  • [ 124467-36-3 ]
  • [ 402-45-9 ]
  • 2-{4-(trifluoromethyl)phenoxy}-7,8-dihydroquinolin-5(6H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 0.5h; ComuMercially available <strong>[124467-36-3]2-chloro-7,8-dihydroquinolin-5(6H)-one</strong> (0.20 g, 1.10 muMol) was dissolved in DMF (5.5mL), and cesium carbonate (0.72 g, 2.20 muMol) and 4-(trifluoromethyl)phenol (0.72 g, 1.65 muMol) were added to thesolution. The mixture was subjected to a reaction at a temperature of 120C for 30 minutes using a microwave reactormanufactured by Biotage. Water was added to the mixture. The organic layer was extracted with ethyl acetate, washedwith saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residuewas purified by silica gel column chromatography (heptane/ethyl acetate = 90/10 -> 60/40) to obtain compound 103-1(0.23 g, 68%).1H NMR (400 MHz, CDCl3, delta): 8.32 (d, J = 8.6 Hz, 1H), 7.68 (d, J = 8.6 Hz, 2H), 7.29 (d, J = 8.6 Hz, 2H), 6.85 (d, J =8.6 Hz, 1H), 2.96 (t, J = 6.1 Hz, 2H), 2.65 (t, J = 6.6 Hz, 2H), 2.15 (tt, J = 6.6, 6.1 Hz, 2H).ESIMS m/z: [M + H]+ 308.
  • 10
  • [ 402-45-9 ]
  • [ 158690-56-3 ]
  • [ 919286-21-8 ]
  • 11
  • [ 402-45-9 ]
  • [ 109431-87-0 ]
  • tert-butyl (S)-3-(4-(trifluoromethyl)phenoxy)pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 21h; Combine (R)-3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester (1.00g, 5.34mmol), 4-(trifluoromethyl)phenol (865mg, 5.34mmol), PPh3 (2.00g, 5.83mmol) Add THF (20mL), transfer to 0C, slowly add DIAD (1.40mL, 7.11mmol), after the addition, transfer the reaction to room temperature for 21h. The reaction solution was concentrated under reduced pressure. The concentrated solution was diluted with methyl tert-butyl ether (30 mL) and stirred at -20C. A large amount of white insoluble solids precipitated. Filtered while cold, and washed the filter cake with cold methyl tert-butyl ether The filtrate was concentrated under reduced pressure, and the concentrated solution was separated by silica gel column chromatography (eluent: PE/EtOAc (v/v)=6/1) to obtain a pale yellow liquid (1.76 g, 100%).
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