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Chemical Structure| 532-02-5 Chemical Structure| 532-02-5

Structure of 532-02-5

Chemical Structure| 532-02-5

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Product Details of [ 532-02-5 ]

CAS No. :532-02-5
Formula : C10H7NaO3S
M.W : 230.22
SMILES Code : O=S(C1=CC=C2C=CC=CC2=C1)([O-])=O.[Na+]
MDL No. :MFCD00064186
InChI Key :YWPOLRBWRRKLMW-UHFFFAOYSA-M
Pubchem ID :23661868

Safety of [ 532-02-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Computational Chemistry of [ 532-02-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 10
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 51.96
TPSA ?

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

65.58 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

-9.35
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

0.63
Log Po/w (WLOGP)?

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

2.82
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.

2.2
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

1.26
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.49

Water Solubility

Log S (ESOL):?

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

-2.09
Solubility 1.86 mg/ml ; 0.0081 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.

-1.58
Solubility 6.03 mg/ml ; 0.0262 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

-3.43
Solubility 0.0857 mg/ml ; 0.000372 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

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

Yes
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.

-7.26 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

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)

2.25

Application In Synthesis of [ 532-02-5 ]

* 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 [ 532-02-5 ]

[ 532-02-5 ] Synthesis Path-Downstream   1~36

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  • [ 613-81-0 ]
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  • [ 143-33-9 ]
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  • [ 613-46-7 ]
  • [ 613-81-0 ]
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  • 5
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  • [ 532-02-5 ]
  • [ 90947-27-6 ]
References: [1]Patent: DE67017, .
  • 10
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  • [ 91-60-1 ]
  • [ 135-19-3 ]
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  • [ 77-78-1 ]
  • [ 5138-53-4 ]
  • 13
  • [ 829-83-4 ]
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  • [ 21498-72-6 ]
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  • [ 829-83-4 ]
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  • [ 21498-59-9 ]
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  • [ 829-83-4 ]
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  • [ 21498-66-8 ]
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  • [ 5138-53-4 ]
  • [ 67-56-1 ]
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  • 18
  • [ 532-02-5 ]
  • [ 52749-46-9 ]
  • [ 1261-18-3 ]
  • 19
  • [ 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%.
  • 24
  • [ 532-02-5 ]
  • [ 1950-76-1 ]
  • 26
  • [ 532-02-5 ]
  • cyanides [ No CAS ]
  • [ 613-46-7 ]
  • 27
  • [ 532-02-5 ]
  • potassium ferro cyanide [ No CAS ]
  • [ 613-46-7 ]
  • 30
  • [ 532-02-5 ]
  • sodium amide [ No CAS ]
  • [ 91-59-8 ]
  • 31
  • [ 532-02-5 ]
  • KSH [ No CAS ]
  • [ 91-20-3 ]
  • [ 5586-15-2 ]
  • [ 91-60-1 ]
  • [ 135-19-3 ]
  • 32
  • [ 532-02-5 ]
  • [ 581-64-6 ]
  • thionine 2-naphthalenesulfonate [ No CAS ]
  • 33
  • [ 204-02-4 ]
  • [ 532-02-5 ]
  • 9-β-naphthalenesulfonylperimidine [ No CAS ]
  • 6-β-naphthalenesulfonylperimidine [ No CAS ]
  • 34
  • clopidogrel hydrobromide [ No CAS ]
  • [ 532-02-5 ]
  • methyl (+)-(S)-α-(o-chlorophenyl)-6,7-dihydrothieno[3,2-a]pyridine-5(4H)acetate 2-naphthalenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; water; at 20℃;Product distribution / selectivity; EXAMPLE 10 Clopidogrel Napsylate, Form A 2.5 g sodium-2-naphthylsulfonate are dissolved in 60 ml of water. Suspended material is separated by filtration. 30 ml methanol and 2.9 g Clopidogrel hydrobromide are then added. The solution obtained is vigorously stirred and put under slight vacuum and kept at room temperature until about 50% by weight of the solvent has slowly evaporated. The white solid thus formed is isolated by vacuum filtration, washed with water and dried under vacuum until constant weight. 3 g Clopidogrel napsylate of Form A are obtained.
  • 35
  • [ 532-02-5 ]
  • [ 120202-66-6 ]
  • methyl (+)-(S)-α-(o-chlorophenyl)-6,7-dihydrothieno[3,2-a]pyridine-5(4H)acetate 2-naphthalenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
52.5 g sodium-2-naphthylsulfonate are dissolved in 430 ml dematerialized water under heating at about 75 C. A solution of 50 g Clopidogrel hydrogen sulfate in 200 ml water is added to the solution. The resulting mixture is cooled to room temperature and the upper oily phase is separated. The separated oil is dissolved in 230 g isopropanol. The obtained solution is dried with magnesium sulfate and diluted with 250 g diisopropylether. The solution is inoculated at a temperature of about 60 C. with Clopidogrel napsylate and stirred over night whilst cooling to room temperature. The solid material is isolated by vacuum filtration, washed with diisopropylether and dried under vacuum. 37 g Clopidogrel napsylate of Form A are obtained with the following properties: HPLC content of Clopidogrel napsylate: 100% DSC: endothermic maximum: 149 C. IR (KBr pressed mass) [cm-1 at % transmission]: 3438 57%; 2969 47%; 2672 63%; 2593 59%; 2362 72%; 1751 10%; 1595 79%; 1475 54%; 1438 53%; 1329 54%; 1301 59%; 1222 11%; 1171 3%; 1135 29%; 1090 21%; 1032 10%; 993 60%; 956 78%; 906 82%; 886 83%; 866 74%; 830 64%; 783 83%; 753 27%; 724 76%; 698 48%; 676 21%; 650 71%; 623 73%; 597 76%; 567 47%; 480 69%; 461 76%; 421 78%. XRPD [Cu Kalpha1]: Angle [2Theta]: Relative intensity [%] 6.79 32 8.27 33 8.59 59 12.44 21 12.62 22 13.07 31 13.55 62 16.87 59 17.24 63 18.25 14 19.00 71 19.69 52 20.02 19 20.24 47 21.34 100 21.82 17 22.40 42 22.72 19 23.02 50 23.27 25 23.65 47 24.75 49 25.09 33 25.34 56 25.85 18 27.11 25 27.61 19 28.12 22 32.14 15 32.55 20 32.97 14 35.10 11
  • 36
  • S-difluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulfonium tetrafluoroborate [ No CAS ]
  • [ 532-02-5 ]
  • difluoromethyl 2-naphthalenesulfonate [ No CAS ]
 

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