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Chemical Structure| 93-11-8 Chemical Structure| 93-11-8

Structure of 93-11-8

Chemical Structure| 93-11-8

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Product Details of [ 93-11-8 ]

CAS No. :93-11-8
Formula : C10H7ClO2S
M.W : 226.68
SMILES Code : O=S(C1=CC=C2C=CC=CC2=C1)(Cl)=O
MDL No. :MFCD00004087
InChI Key :OPECTNGATDYLSS-UHFFFAOYSA-N
Pubchem ID :7125

Safety of [ 93-11-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P260-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310
Class:8
UN#:3261
Packing Group:

Computational Chemistry of [ 93-11-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 10
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 57.03
TPSA ?

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

42.52 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.94
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

2.52
Log Po/w (WLOGP)?

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

3.85
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.

2.56
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

2.38
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.65

Water Solubility

Log S (ESOL):?

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

-3.3
Solubility 0.115 mg/ml ; 0.000506 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.

-3.06
Solubility 0.198 mg/ml ; 0.000873 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

-4.62
Solubility 0.00543 mg/ml ; 0.0000239 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

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.

-5.89 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<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)

1.9

Application In Synthesis of [ 93-11-8 ]

* 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 [ 93-11-8 ]

[ 93-11-8 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 33105-81-6 ]
  • [ 93-11-8 ]
  • [ 143688-71-5 ]
  • 2
  • [ 93-11-8 ]
  • [ 21495-41-0 ]
  • 2-methyl-<i>N</i>-(naphthalene-2-sulfonyl)-tryptophan [ No CAS ]
  • 3
  • [ 532-02-5 ]
  • [ 93-11-8 ]
YieldReaction ConditionsOperation in experiment
95.8% With trichlorophosphate; In chloroform; at 90℃; for 9h; 1) 346 g (1.5 mol) of sodium 2-naphthalenesulfonate and 770 g (5 mol) of phosphorus oxytrichloride were successively added to 2.25 mol of chloroform to obtain a reaction solution a;2) The reaction liquid a obtained in the step 1) is reacted at a temperature of 90 C for 9 hours to obtain a mixed liquid b;3) the step 2) obtained by the mixture b continued to steam out the excess of phosphorus oxychloride and chloroform, followed by washing, filtration, vacuum distillation, in 2 - naphthalene sulfonyl chloride.It was calculated that the product yield of the 2-naphthalenesulfonyl chloride was 95.8%.
  • 4
  • [ 45865-42-7 ]
  • [ 93-11-8 ]
  • N-(5-tert-butyl-4-methyl-1,3-thiazol-2-yl)naphthalene-2-sulfonamide [ No CAS ]
  • 5
  • [ 1738-72-3 ]
  • [ 121-44-8 ]
  • [ 93-11-8 ]
  • [ 606-25-7 ]
YieldReaction ConditionsOperation in experiment
93% In dichloromethane; To a solution of 2-naphthalene sulfonyl chloride (3 g, 13.23 mmol) and serine benzylester (3.07 g, 13.23 mmol) in 120 mL CH2 Cl2 was added Et3 N (5.53 mL, 13.23 mmol) at 0 C. The reaction was stirred at room temperature for 1 hr and washed with a saturated (sat.) solution of KHSO4, brine, and dried over Na2 SO4. The organic layer was concentrated in vacuo to give the naphthylsulfonamide (93%).
  • 6
  • [ 208837-83-6 ]
  • [ 93-11-8 ]
  • [ 914937-17-0 ]
YieldReaction ConditionsOperation in experiment
82% With triethylamine; In dichloromethane; at 0 - 20℃; 2-Naphtalenesulphonyl chloride (20.07g, 97.39mmol) was added in one portion to a solution of intermediate B (17.53g, 88.54mmol) and Et3N (24.7ml, 177.07mmol) in anhydrous DCM (270ml) at O0C under N2, giving a light brown solution which was allowed to warm to r.t. overnight. The reaction mixture was diluted with DCM (200ml) and sat. NaHCO3 (200ml). The organic phase was separated and washed with H2O (2 x 200ml), dried (Na2SO4), filtered and concentrated in vacuo to give a pale yellow oil. Trituration with TME and heptane gave a solid which was isolated by filtration and washed with heptane to give the title compound as a white solid (27.99g, 82%). LCMS purity 100%, m/z 389 [M+H]+, 1H NMR (300 MHz, CDCI3) δ: 1.35 (9H, s), 1.82 (2H, m), 1.96 (1 H, m), 3.29-3.34 (2H, m), 3.41-3.56 (2H, m), 5.12 (1 H, br s), 7.62- 7.68 (2H, m), 7.85 (1 H, m), 7.93 (1 H, d), 7.99-8.02 (2H, m), 8.47 (1 H, m).
  • 7
  • [ 120351-94-2 ]
  • [ 93-11-8 ]
  • 3-[2-(2-naphthalenesulfonylamino)ethoxy]benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; In N-methyl-acetamide; Step 1 Synthesis of 3-[2-(2-naphthalenesulfonylamino)ethoxy]benzonitrile: 163 mg of <strong>[120351-94-2]3-(2-aminoethoxy)benzonitrile</strong> and 0.5 ml of diisopropylethylamine were dissolved in 10 ml of dimethylformamide. A solution of 250 mg (1.1 mmol) of 2-naphthalenesulfonyl chloride in dimethylformamide was added to the obtained solution under cooling with ice, and they were stirred under cooling with ice for 2 hours. The title compound was obtained by the same isolation process as that of step 1 in Example 1 with ethyl acetate as the extractant. Yield: 320 mg (0.91 mmol) (91 %) H-NMR (CDCl3) delta 3.45 (2H, dt), 4.00(2H, t), 5.05(1H, br), 6.96 (1H, s),6.97 (1H, d), 7.20 (1H, d), 7.30 (1H, t), 7.59-7.70 (2H, m), 7.82-7.98(4H, m), 8.46 (1H, s)
  • 8
  • [ 59378-87-9 ]
  • [ 93-11-8 ]
  • [ 1394241-84-9 ]
 

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Technical Information

Categories

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