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Chemical Structure| 13214-64-7 Chemical Structure| 13214-64-7

Structure of 13214-64-7

Chemical Structure| 13214-64-7

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CAS No.: 13214-64-7

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Product Details of [ 13214-64-7 ]

CAS No. :13214-64-7
Formula : C10H11NO4
M.W : 209.20
SMILES Code : COC1=CC=C(C=C1)C(=O)NCC(O)=O
MDL No. :MFCD00181815
InChI Key :SIEIOUWSTGWJGE-UHFFFAOYSA-N
Pubchem ID :128847

Safety of [ 13214-64-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 13214-64-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 6
Fraction Csp3 0.2
Num. rotatable bonds 5
Num. H-bond acceptors 4.0
Num. H-bond donors 2.0
Molar Refractivity 52.51
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

75.63 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.5
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.24
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.51
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.58
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

0.71
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.61

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.95
Solubility 23.4 mg/ml ; 0.112 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.89
Solubility 26.9 mg/ml ; 0.129 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.31
Solubility 1.02 mg/ml ; 0.00489 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-7.75 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.26

Application In Synthesis of [ 13214-64-7 ]

* 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 [ 13214-64-7 ]

[ 13214-64-7 ] Synthesis Path-Downstream   1~30

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YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In 1,4-dioxane; water; at 4℃; for 20.75h; 4.1 N-(4-Methoxybenzoyl)glycine 2.93 g (39 mmol) of glycine dissolved in 41 ml of aqueous 1N sodium hydroxide solution are placed in a 250 ml round-bottomed flask, the mixture is cooled to 4° C., 41 ml of aqueous 1N sodium hydroxide solution and a solution of 7 g (0.041 mol) of 4-methoxybenzoyl chloride in 10 ml of dioxane are added simultaneously, dropwise over 45 minutes, and the mixture is stirred for 20 hours. Concentrated aqueous hydrochloric acid solution is added to pH 1 and the precipitate formed is collected by filtration and recrystallized from isopropyl alcohol. 3.74 g of product are obtained. Melting point: 173° C.
With sodium hydroxide; for 0.5h; General procedure: Glycine (5.0 g, 66.7 mmol) was dissolved in 50 mL of 10percent NaOH solution. BzCl (10.79 mL, 93.0 mmol) was added to the solution and stirred vigorously for 30 min. Crushed ice (60 g) was added to the solution and then concentrated HCl was added dropwise until the mixture was acidified (pH 2-3). The precipitate was filtrated and washed with distilled water until neutrality. The product 2-benzamidoacetic acid was obtained after drying in vacuum.
With sodium hydroxide; General procedure: Glycine (133.0 mmol) wasdissolved in 10percent sodium hydroxide solution (100mL),and then benzoyl chloride (186.0 mmol) was added in portions tothis solution, stirred vigorously after each addition. Crushedice (100 g)was added to the solution and then concentrated HClwas added dropwise until the mixture was acidified (pH2-3). The resulting compounds1a-1g were obtained as whitecrystalline solid. All spectroscopic data of 1a-g[1-3]are in good agreement with the literature reported data
With sodium hydroxide; at 20℃; for 4h; Add 10 mL of 10percent NaOH solution to a 50 mL three-necked flask, add 0.75 g of glycine to dissolve, slowly add 1.71 g of 4-methoxybenzoyl chloride dropwise, stir at room temperature for 4 h, adjust the pH to 1-2 with hydrochloric acid, and precipitate a white solid. Tetrahydrofuran: Toluene = 2:1 recrystallization purification to carry out the next condensation reaction.1.0 mmol of the compound VII, 1.0 mmol of the prepared carboxylic acid in 20 mL of CH 2 Cl 2 , the temperature was controlled at about 0 ° C, and 1.2 mmol of EDCI, 2.0 mmol of DIPEA, 1.2 mmol of HOBt were added in sequence, and the reaction was stirred at room temperature overnight. After washing with 10 mL of a 5percent HCl solution, 10 mL of a 5percent NaHCO 3 solution, and 10 mL of a saturated brine, the mixture was dried over anhydrous Na 2 SO 4 and then evaporated to dryness. White solid, yield 58percent

References: [1]Tetrahedron,1984,vol. 40,p. 327 - 337.
[2]Journal of Chemical Sciences,2011,vol. 123,p. 335 - 341.
[3]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 1904 - 1924.
[4]Chemistry of Heterocyclic Compounds,1980,vol. 16,p. 701 - 703.
    Khimiya Geterotsiklicheskikh Soedinenii,1980,p. 909 - 911.
[5]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2008,vol. 47,p. 932 - 937.
[6]Arzneimittel-Forschung/Drug Research,1954,vol. 4,p. 575,578.
[7]Chemistry of Heterocyclic Compounds,1980,vol. 16,p. 701 - 703.
    Khimiya Geterotsiklicheskikh Soedinenii,1980,p. 909 - 911.
[8]Journal of the American Chemical Society,1980,vol. 102,p. 6828 - 6837.
[9]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 3100 - 3104.
[10]Journal of Medicinal Chemistry,1989,vol. 32,p. 1033 - 1038.
[11]Il Farmaco,1998,vol. 53,p. 439 - 442.
[12]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 37 - 41.
[13]Patent: US2004/29884,2004,A1 .Location in patent: Page/Page column 2.
[14]Heterocycles,2011,vol. 83,p. 153 - 161.
[15]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4642 - 4647.
[16]Biopharmaceutics and Drug Disposition,2011,vol. 32,p. 343 - 354.
[17]Synthetic Communications,2013,vol. 43,p. 1538 - 1542.
[18]Tetrahedron,2013,vol. 69,p. 7019 - 7025.
[19]Tetrahedron Letters,2015,vol. 56,p. 851 - 855.
[20]Medicinal Chemistry Research,2016,vol. 25,p. 1239 - 1249.
[21]Journal of the Chinese Chemical Society,2016,vol. 63,p. 909 - 916.
[22]Archiv der Pharmazie,2017,vol. 350.
[23]Journal of Enzyme Inhibition and Medicinal Chemistry,2018,vol. 33,p. 629 - 638.
[24]Patent: CN109232552,2019,A .Location in patent: Paragraph 0027.
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  • [ 122-51-0 ]
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  • 4-ethoxymethylene-2-(4-methoxy-phenyl)-4<i>H</i>-oxazol-5-one [ No CAS ]
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  • [ 50284-74-7 ]
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  • 4-(3-methoxy-allylidene)-2-(4-methoxy-phenyl)-4<i>H</i>-oxazol-5-one [ No CAS ]
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  • [ 6203-18-5 ]
  • [ 110194-33-7 ]
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  • [ 75152-19-1 ]
YieldReaction ConditionsOperation in experiment
With diisopropyl-carbodiimide; In dichloromethane; at 0℃; for 1h;Inert atmosphere; General procedure: A solution of 1 (0.5 mmol) in CH2Cl2 (5 mL) in a round-bottom flask (25 mL) was cooled with ice-water, and then DIC (0.55 mmol) was added by a syringe. After the resultant mixture was stirred at 0 °C for 1 h, CH2Cl2 was removed by sparging N2 followed by adding 3a (0.55 mmol) or 3b (0.6 mmol) and toluene (10 mL). After refluxing for 3 h, the reaction mixture was diluted with EtOAc (6 mL), passed through a silica gel column, and then evaporated. The product 5a or 5b was isolated from the residue by preparative TLC (silica gel, EtOAc/PE 1/2-1/1, v/v).
With acetic anhydride;Heating; General procedure: A mixture of benzoyl glycines 1a?1d (0.02 mol) and 75 cm3 acetic anhydride was gently heated until a clear solution 2a?2d was obtained. The resulting solution(A) was cooled in an ice bath before treating with a solution (B) of naphthalene diazonium chloride prepared as follows: 3.2 g 1-naphthylamine (0.02 mol) was mixed with 5 cm3 H2O and 6 cm3 conc. HCl. The mixture was cooled in an ice bath and an aqueous solution of 1.38 g NaNO2(0.02 mol) was introduced dropwise and the resulting mixture was stirred for further 30 min. Freshly prepared crude solution (A) was added dropwise in the presence of 1.64 g anhydrous sodium acetate (0.02 mol) and the stirring was continued for further 2 h at 0 C. The resulting crude precipitate was filtered, washed with water, and dried
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  • [ 75152-16-8 ]
  • 24
  • [ 100-34-5 ]
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  • 2-(4-Methoxy-phenyl)-4-(phenyl-hydrazono)-4H-oxazol-5-one [ No CAS ]
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  • [ 54926-15-7 ]
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  • [ 100-09-4 ]
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  • [ 75152-19-1 ]
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  • [ 68-12-2 ]
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  • 4-[1-Dimethylamino-meth-(Z)-ylidene]-2-(4-methoxy-phenyl)-4H-oxazol-5-one [ No CAS ]
 

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