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Chemical Structure| 123664-84-6 Chemical Structure| 123664-84-6

Structure of 123664-84-6

Chemical Structure| 123664-84-6

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Product Details of [ 123664-84-6 ]

CAS No. :123664-84-6
Formula : C14H15NO4S
M.W : 293.34
SMILES Code : CS(=O)(NC1=CC(OC)=CC=C1OC2=CC=CC=C2)=O
MDL No. :MFCD13152085
Boiling Point : No data available
InChI Key :HKQJXMJGWKDFTA-UHFFFAOYSA-N
Pubchem ID :10803650

Safety of [ 123664-84-6 ]

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

Computational Chemistry of [ 123664-84-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 20
Num. arom. heavy atoms 12
Fraction Csp3 0.14
Num. rotatable bonds 5
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 77.72
TPSA ?

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

73.01 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.92
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

2.74
Log Po/w (WLOGP)?

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

3.75
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.

1.58
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

1.57
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.31

Water Solubility

Log S (ESOL):?

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

-3.5
Solubility 0.093 mg/ml ; 0.000317 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-3.93
Solubility 0.0346 mg/ml ; 0.000118 mol/l
Class?

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

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

-5.14
Solubility 0.00213 mg/ml ; 0.00000726 mol/l
Class?

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

Moderately 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

Yes
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

Yes
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

Yes
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

Yes
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

Yes
Log Kp (skin permeation)?

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

-6.14 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.

0.55

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

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<0.0
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)

2.85

Application In Synthesis of [ 123664-84-6 ]

* 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 [ 123664-84-6 ]

[ 123664-84-6 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 6011-14-9 ]
  • [ 123664-84-6 ]
  • α-amino-2-methoxy-4-methanesulfonamido-5-phenoxyacetophenone hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
157.6 g With hydrogenchloride; aluminum (III) chloride; water; In nitromethane; at 10 - 20℃; for 16.0h; Add to a 1000 mL reaction flask300 mL of nitromethane,Adding 203 g of anhydrous aluminum trichloride in portions, After cooling to room temperature, add 114g aminoacetonitrile hydrochloride; to a temperature below 20 C, 150 g of intermediate III (<strong>[123664-84-6]4-phenoxy-3-methanesulfonamidoanisole</strong>) was added; after stirring for 10 minutes, a dry hydrogen chloride gas was introduced, Ventilation for about 15h, the end of the reaction. The reaction solution was slowly added to 1200 g of 2 mol / L dilute hydrochloric acid at a controlled temperature of 10 C or less, for stirring 1h, filter, solid with a small amount of water (about 80mL) washing, drying; and then 150mL ethyl acetate beating, filter dry,Dry; then the solid and then twice the volume of 95% (volume percentage) of ethanol reflux lh cooling, filtration, solid bake to moisture qualified,157.6 g of the final product (alpha-amino-2-methoxy-4-methanesulfonamido-5-phenoxyacetophenone hydrochloride), 105.07% by weight, and a purity of 99.49% For 168.8 to 17.1.4 C.
  • 2
  • [ 79-03-8 ]
  • [ 123664-84-6 ]
  • [ 123665-04-3 ]
  • 3
  • [ 76838-72-7 ]
  • [ 124-63-0 ]
  • [ 123664-84-6 ]
YieldReaction ConditionsOperation in experiment
91.9% With hydrogenchloride; In pyridine; water; ethyl acetate; (4) 10.0 g of 3-amino-4-phenoxyanisole was dissolved in 50 ml of pyridine. Thereto was dropwise added 5.59 g of methanesulfonyl chloride in 10 minutes with ice-cooling. The mixture was stirred for 1 hour at 20-25 C. The reaction mixture was introduced into a mixture of 200 ml of ethyl acetate and 100 ml of water. The resulting organic layer was separated and washed with three 100-ml portions of 2N hydrochloric acid and then with a saturated aqueous sodium chloride solution. The organic layer was separated, dried with anhydrous magnesium sulfate, and subjected to distillation under reduced pressure to remove the solvent. The resulting crystal was recrystallized from isopropyl alcohol to obtain 12.5 g (yield: 91.9%) of 3-methylsulfonylamino4-phenoxyanisole having a melting point of 109.5-111 C. IR (KBr) cm-1: 3250, 1610, 1585, 1480, 1320, 1220, 1150 NMR (CDCl3)delta: 2.94 (3H, s), 3.81 (3H, s), 6.36-7.43 (9H, m)
276.47 g With pyridine; at 5 - 30℃; for 1.5h;Green chemistry; (1) 169 g of 4-methoxy-2 nitrophenol was dissolved in a mixture of 1500 ml of 70% ethanol and 40 ml of 4N HCl, the reaction liquid was heated to 75 C; Then, 196 g of iron powder was uniformly added to the reaction liquid in three batches in 20 minutes. The reaction was stirred rapidly and controlled to no starting material. After completion of the reaction, a saturated solution of sodium carbonate was added to adjust pH = 9 to obtain 2-amino-4-methoxyphenol. (2) 84 g of powdered potassium hydroxide prepared in (1) was added to 2-amino-4-methoxyphenol, stirred, and heated at 160 C for 3.5 hours, and the reaction was completed to obtain a dry salt; 1.89 g of copper powder and 188.4 g of bromobenzene were sequentially added thereto, and stirred at 180 C, mix to discoloration, heat to 200 C, and heat for 2 hours. After cooling, 1200 ml of water and 300 ml of diethyl ether were poured and distilled to give 3-amino-4-phenoxy-anisole. (3) The 3-amino-4-phenoxy-anisole prepared in (2) was dissolved in 800 ml of anhydrous pyridine, the solution was cooled to 5 C, and 137.5 g of methylsulfonyl chloride was added dropwise. After completion of the dropwise addition, the reaction was stirred at room temperature at 30 C, and a developing solvent (EA:PE volume ratio of 1:3) was added thereto, and the raw material was controlled until no raw material, and the reaction time was 1.5 h. After the reaction was completed, the reaction solution was poured into water and extracted with ethyl acetate. Twice, combining organic phases; Wash with 2N HCl until the aqueous layer is pH <7, then washed twice with water, dried over anhydrous magnesium sulfate, and then evaporated to ethyl ether. (5-methoxy-2-phenoxy - benzenesulfonamide quality 276.47g, a purity of 99.658%, 93.93% yield).
  • 4
  • [ 75-36-5 ]
  • [ 123664-84-6 ]
  • [ 123664-52-8 ]
  • 5
  • [ 141-75-3 ]
  • [ 123664-84-6 ]
  • <i>N</i>-(4-butyryl-5-hydroxy-2-phenoxy-phenyl)-methanesulfonamide [ No CAS ]
  • 6
  • [ 645-45-4 ]
  • [ 123664-84-6 ]
  • <i>N</i>-[5-hydroxy-2-phenoxy-4-(3-phenyl-propionyl)-phenyl]-methanesulfonamide [ No CAS ]
  • 7
  • [ 84594-95-6 ]
  • [ 123664-84-6 ]
  • 8
  • [ 10298-80-3 ]
  • [ 123664-84-6 ]
  • 9
  • [ 123664-84-6 ]
  • [ 123662-55-5 ]
  • 10
  • [ 123664-84-6 ]
  • N-(4-oxo-2-methyl-6-phenoxy-4H-7-chromenyl)methanesulfonamide [ No CAS ]
  • 11
  • [ 123664-84-6 ]
  • [ 123664-21-1 ]
  • 12
  • [ 123664-84-6 ]
  • <i>N</i>-(3-methyl-4-oxo-6-phenoxy-4<i>H</i>-chromen-7-yl)-methanesulfonamide [ No CAS ]
  • 13
  • [ 123664-84-6 ]
  • [ 123664-34-6 ]
  • 14
  • [ 123664-84-6 ]
  • N-(4-oxo-2-ethyl-6-phenoxy-4H-7-chromenyl)methanesulfonamide [ No CAS ]
  • 15
  • [ 123664-84-6 ]
  • [ 123663-48-9 ]
  • 16
  • [ 123664-84-6 ]
  • <i>N</i>-(3-ethyl-4-oxo-6-phenoxy-4<i>H</i>-chromen-7-yl)-methanesulfonamide [ No CAS ]
  • 17
  • [ 123664-84-6 ]
  • 2-formylamino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one [ No CAS ]
  • 19
  • [ 123664-84-6 ]
  • [ 149456-98-4 ]
  • 20
  • [ 123664-84-6 ]
  • [ 149457-03-4 ]
  • 21
  • [ 123664-84-6 ]
  • 7-methanesulfonylamino-4-oxo-6-phenoxy-4<i>H</i>-chromene-3-carbonyl chloride [ No CAS ]
  • 22
  • [ 123664-84-6 ]
  • [ 123663-69-4 ]
  • 23
  • [ 123664-84-6 ]
  • [ 123663-72-9 ]
  • 24
  • [ 123664-84-6 ]
  • [ 123664-65-3 ]
  • 25
  • [ 123664-84-6 ]
  • [ 123663-75-2 ]
  • 26
  • [ 123664-84-6 ]
  • [ 123664-54-0 ]
  • 27
  • [ 123664-84-6 ]
  • [ 123663-74-1 ]
  • 28
  • [ 123664-84-6 ]
  • 7-methanesulfonylamino-4-oxo-6-phenoxy-4<i>H</i>-chromene-3-carboxylic acid methylamide [ No CAS ]
  • 29
  • [ 123664-84-6 ]
  • [ 123664-66-4 ]
  • 30
  • [ 123664-84-6 ]
  • N-[7-[(methylsulfonyl)amino]-4-oxo-6-phenoxy-4H-1-benzopyran-3-yl]acetamide [ No CAS ]
  • 31
  • [ 123664-84-6 ]
  • [ 123663-68-3 ]
  • 32
  • [ 123664-84-6 ]
  • [ 123664-56-2 ]
  • 33
  • [ 123664-84-6 ]
  • 7-[(methylsulfonyl)amino]-4-oxo-6-phenoxy-4H-1-benzopyran-2-carboxamide [ No CAS ]
  • 34
  • [ 123664-84-6 ]
  • N-[7-[(methylsulfonyl)amino]-4-oxo-6-phenoxy-4H-1-benzopyran-2-yl]acetamide [ No CAS ]
  • 35
  • [ 123664-84-6 ]
  • 7-methanesulfonylamino-4-oxo-6-phenoxy-4<i>H</i>-chromene-3-carboxylic acid dimethylamide [ No CAS ]
 

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