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[ CAS No. 273-53-0 ] {[proInfo.proName]}

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Chemical Structure| 273-53-0
Chemical Structure| 273-53-0
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Product Citations

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.

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Product Details of [ 273-53-0 ]

CAS No. :273-53-0 MDL No. :MFCD00005765
Formula : C7H5NO Boiling Point : -
Linear Structure Formula :- InChI Key :BCMCBBGGLRIHSE-UHFFFAOYSA-N
M.W : 119.12 Pubchem ID :9228
Synonyms :

Calculated chemistry of [ 273-53-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 34.01
TPSA : 26.03 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.72
Log Po/w (XLOGP3) : 1.59
Log Po/w (WLOGP) : 1.83
Log Po/w (MLOGP) : 0.98
Log Po/w (SILICOS-IT) : 2.02
Consensus Log Po/w : 1.63

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.32
Solubility : 0.57 mg/ml ; 0.00478 mol/l
Class : Soluble
Log S (Ali) : -1.75
Solubility : 2.13 mg/ml ; 0.0179 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.86
Solubility : 0.163 mg/ml ; 0.00137 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.04

Safety of [ 273-53-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 273-53-0 ]

* 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 [ 273-53-0 ]
  • Downstream synthetic route of [ 273-53-0 ]

[ 273-53-0 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 273-53-0 ]
  • [ 615-18-9 ]
YieldReaction ConditionsOperation in experiment
89% With tetrachloromethane; sodium t-butanolate In N,N-dimethyl-formamide at 20℃; for 3 h; Benzoxazole (1 mmol, 119.1 mg),Carbon tetrachloride (1.1 mmol, 169.2 mg) was placed in a 10 mL round bottom flask.Added 5 mL of N,N-dimethylformamide and sodium tert-butoxide (4.0 mmol, 384.4 mg).Stir at room temperature for 3 hours,TLC monitored the endpoint of the reaction.The mixture was poured into water and extracted with dichloromethane. The organic phase was collected and dried. The dichloromethane was removed by rotary evaporation to give the crude product.The crude product was subjected to silica gel column chromatography with petroleum ether and ethyl acetate as eluent (volume ratio = 30:1).2-Chlorobenzoxazole (light yellow oily liquid, 136.7 mg, yield 89percent) was obtained.
Reference: [1] Patent: CN107501023, 2017, A, . Location in patent: Paragraph 0065; 0066
[2] Journal of Organometallic Chemistry, 1999, vol. 588, # 2, p. 155 - 159
[3] Synthesis (Germany), 2013, vol. 45, # 7, p. 936 - 942
  • 2
  • [ 273-53-0 ]
  • [ 3621-82-7 ]
  • [ 615-18-9 ]
Reference: [1] Patent: US6274739, 2001, B1,
  • 3
  • [ 273-53-0 ]
  • [ 14236-72-7 ]
  • [ 13673-62-6 ]
  • [ 93-55-0 ]
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 18, p. 2344 - 2347
  • 4
  • [ 273-53-0 ]
  • [ 17200-30-5 ]
  • [ 70886-33-8 ]
Reference: [1] Yakugaku Zasshi, 1953, vol. 73, p. 1316[2] Chem.Abstr., 1955, p. 299
  • 5
  • [ 273-53-0 ]
  • [ 17200-30-5 ]
  • [ 70886-33-8 ]
Reference: [1] Yakugaku Zasshi, 1953, vol. 73, p. 1316[2] Chem.Abstr., 1955, p. 299
  • 6
  • [ 273-53-0 ]
  • [ 2382-96-9 ]
YieldReaction ConditionsOperation in experiment
92.6% With 1.3-propanedithiol; potassium hydroxide In dimethyl sulfoxide at 130℃; for 12 h; Inert atmosphere; Sealed tube Benzoxazole 119.12 mg (1.0 mmol) and 1,3-propanedithiol 325 μL (3.0 mmol), potassium hydroxide 280.55 mg (5.0 mmol), 3 mL DMSO, placed in a reaction tube equipped with a magnetic stir bar The mixture was sealed with argon, heated and stirred, and reacted in an oil bath at 130 ° C for 12 hours. After the reaction is completed, the reaction solution is transferred to a separating funnel with water washing, an appropriate amount of dilute sulfuric acid is added, the pH of the aqueous phase is adjusted to 1-3, and the organic phase is extracted with ethyl acetate, and the upper organic phase is transferred with anhydrous magnesium sulfate. dry.The mixture was decanted under reduced pressure and subjected to column chromatography to give a brown solid product (140 mg).The yield was 92.6percent.
Reference: [1] Patent: CN108530374, 2018, A, . Location in patent: Paragraph 0022; 0023
[2] Organic and Biomolecular Chemistry, 2017, vol. 15, # 39, p. 8276 - 8279
  • 7
  • [ 273-53-0 ]
  • [ 591-50-4 ]
  • [ 2688-84-8 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 35, p. 6856 - 6860
  • 8
  • [ 273-53-0 ]
  • [ 124-38-9 ]
  • [ 74-88-4 ]
  • [ 27383-86-4 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With 3-benzyl-1-(1-((2,6-diisopropylphenyl)imino)ethyl)-1H-imidazol-3-ium chloride; potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 80℃; for 18 h; Inert atmosphere
Stage #2: at 65℃; for 1 h; Inert atmosphere
In the reaction flask, Under argon, a catalyst (9.9 mg, 0.025 mmol, 5 molpercent), Potassium tert-butoxide (0.0672 g, 0.6 mmol), DMF (3.0 mL) Benzoxazole (50.7 μl, 0.5 mmol), carbon dioxide gas, The reaction was stirred at 80 ° C for 18 hours under normal pressure. Cooled to 65 ° C, Methyl iodide (93 μl, 1.5 mmol) was added and the reaction was stirred at 65 ° C for 1 hour. The reaction was quenched with deionized water and the reaction product was extracted with ethyl acetate. The yield was 95percent by gas chromatography, The column chromatography was carried out in a volume ratio of ethyl acetate / petroleum ether 1:10 mixed solvent as developing solvent) in a yield of 90percent.
Reference: [1] Green Chemistry, 2018, vol. 20, # 5, p. 989 - 996
[2] Organic Letters, 2010, vol. 12, # 15, p. 3567 - 3569
[3] Journal of the American Chemical Society, 2010, vol. 132, # 26, p. 8858 - 8859
[4] Patent: CN106565623, 2017, A, . Location in patent: Paragraph 0021
[5] Angewandte Chemie - International Edition, 2010, vol. 49, # 46, p. 8670 - 8673
  • 9
  • [ 273-53-0 ]
  • [ 27383-86-4 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 15, p. 3986 - 3989
[2] Patent: US2013/85276, 2013, A1,
[3] Green Chemistry, 2016, vol. 18, # 13, p. 3804 - 3807
  • 10
  • [ 273-53-0 ]
  • [ 10075-73-7 ]
  • [ 5089-22-5 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 6, p. 1601 - 1604
  • 11
  • [ 90-02-8 ]
  • [ 273-53-0 ]
  • [ 94-67-7 ]
YieldReaction ConditionsOperation in experiment
28% With acetylhydroxamic acid; sulfuric acid In acetonitrile at 80℃; for 0.133333 h; Microwave irradiation General procedure: 2-Hydroxy acetophenone 4a (1.0 g, 7.4 mmol), acetohydroxamic acid (0.83 g, 11.0 mmol), acetonitrile (3 ml), and conc. H2SO4 (0.2 ml) were taken into a 10 ml pressure tube and subjected to microwave heating (CEM discover, 360 W, 80 °C, 25 psi) for 8 min. Next, the reaction mixture was diluted with ethyl acetate (3 ml) and to this; saturated sodium bicarbonate solution (5 ml) was added drop-wise. The mixture was extracted with ethyl acetate (2 .x. 10 ml) and the combined organic layer was washed with saturated NaCl solution, dried over anhy. Na2SO4, and concentrated under reduced pressure. Purification of the mixture by normal column chromatography (silica gel 60-120 mesh, ethyl acetate/hexane: 1:9) gave benzoxazole 5a (0.67 g, 70percent) in the form of a yellow oil and 2-hydroxy acetophenone oxime 6a (68 mg, 6percent, mp 104-107 °C) in the form of a white powder.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 46, p. 6103 - 6107
  • 12
  • [ 273-53-0 ]
  • [ 141103-93-7 ]
Reference: [1] Heterocycles, 1994, vol. 38, # 1, p. 5 - 8
[2] Journal of the Chemical Society, Chemical Communications, 1992, # 5, p. 404 - 406
  • 13
  • [ 273-53-0 ]
  • [ 154264-95-6 ]
Reference: [1] Heterocycles, 1994, vol. 38, # 1, p. 5 - 8
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