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Chemical Structure| 105807-83-8 Chemical Structure| 105807-83-8

Structure of 105807-83-8

Chemical Structure| 105807-83-8

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Product Details of [ 105807-83-8 ]

CAS No. :105807-83-8
Formula : C10H12N2O2
M.W : 192.21
SMILES Code : NC1=CC2=C(C=C1)NC(C(O2)(C)C)=O
MDL No. :MFCD11048439
InChI Key :UXMAGPQBCODAEJ-UHFFFAOYSA-N
Pubchem ID :13665546

Safety of [ 105807-83-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 105807-83-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.3
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 57.32
TPSA ?

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

64.35 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.6
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

0.78
Log Po/w (WLOGP)?

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

0.81
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.

0.56
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

1.24
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.0

Water Solubility

Log S (ESOL):?

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

-1.84
Solubility 2.78 mg/ml ; 0.0144 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.

-1.71
Solubility 3.73 mg/ml ; 0.0194 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

-3.04
Solubility 0.177 mg/ml ; 0.00092 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.

-6.92 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

1.0
Bioavailability Score?

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

0.55

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

1.0 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)

2.16

Application In Synthesis of [ 105807-83-8 ]

* 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 [ 105807-83-8 ]

[ 105807-83-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 85160-83-4 ]
  • [ 105807-83-8 ]
YieldReaction ConditionsOperation in experiment
73.4% With iron; ammonium chloride; In ethanol; water; at 90℃; 30 mM 2,2-dimethyl-7-nitro-2H-1,4-benzoxazol-3 (4H) -one was added100 mL of solvent (EtOH: H20 = 3: 1)Under stirring at room temperature, 10 mM ammonium chloride and 30 mM iron powder were further added, and the mixture was heated to 90 C. and refluxed for 1-2 hours.After the TLC detection of the reaction is over, the excess iron powder is filtered while hot, after the reaction solution is cooled and the solvent is distilled off under reduced pressure,The residual solid was adjusted to pH 10 with an aqueous solution of potassium carbonate, precipitated with a solid, filtered,The filter cake was washed with cooling water and dried in vacuo to give pure intermediate product as 4.23 g of a yellow powder,Yield 73.4%. This intermediate was used directly in the next reaction without further purification
66% With 20% palladium hydroxide-activated charcoal; hydrogen; In methanol; at 40℃; under 750.075 Torr; for 4h; (2) Preparation of 7-amino-2,2-dimethyl-2H-1,4-benzoxazin-3(4H)-one A mixture of the compound (wet material: 384.6 g) obtained in the above step (1), methanol (2880 mL), and 20% palladium hydroxide carbon (13.8 g) was stirred under hydrogen pressure (0.1 MPa) at 40C until hydrogen absorption terminated (about 4 hours). The reaction mixture was filtered, and the unfiltered residue was washed with methanol (300 mL). The filtrate and the washings were combined, then concentrated under reduced pressure at 50C or lower, to the residue were added methanol (288 mL) and water (1440 mL), and the mixture was stirred at 50C for about 1 hour. The mixture was cooled to 25C, then stirred for 30 minutes, the precipitated crystals were collected by filtration, washed with water (1440 mL), and then dried to obtain the title compound (163.94 g) as red-brown crystals (yield: 66%, purity: 100%). MS: ESI-MS m/Z: 193 [M+H]+ 1 H-NMR (CDCl3): delta 1.51 (6H, s), 3.56 (2H, brs), 6.29 (1H, dd), 6.32, 6.33 (1H, m), 6.59 (1H, d), 8.34 (1H, brs)
With hydrogen;palladium 10% on activated carbon; In tetrahydrofuran; methanol; at 20℃; To a solution of the compound obtained in Reference Example 1(1) (500 mg) in tetrahydrofuran (7 mL)-methanol (5 mL) was added 10% palladium-carbon (100 mg, water content: ca. 50%), and the mixture was stirred overnight at room temperature <n="76"/>under atmospheric pressure of hydrogen. The insolubles were removed by filtration, and the filtrate was concentrated in vacuo to give 7-amino-2,2-dimethyl~2H-l,4- benzoxazin- 3(4H)-one (429 mg) as a pale pink solid. MS(APCI) m/z: 193 [M+H]+
  • 2
  • [ 105807-83-8 ]
  • [ 26638-43-7 ]
  • methyl 2-(N-(2,2-dimethyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)sulfamoyl)benzoate [ No CAS ]
  • 3
  • [ 351003-48-0 ]
  • [ 105807-83-8 ]
  • 3-chloro-N-(2,2-dimethyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)-2-fluorobenzenesulfonamide [ No CAS ]
 

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Technical Information

Categories

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