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Chemical Structure| 113713-60-3 Chemical Structure| 113713-60-3

Structure of 113713-60-3

Chemical Structure| 113713-60-3

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Product Details of [ 113713-60-3 ]

CAS No. :113713-60-3
Formula : C7H7N3OS
M.W : 181.22
SMILES Code : COC2=CC=C1N=C([NH]C1=N2)S
MDL No. :MFCD06658230
InChI Key :PNYFSMIUARCIRR-UHFFFAOYSA-N
Pubchem ID :11126879

Safety of [ 113713-60-3 ]

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

Computational Chemistry of [ 113713-60-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 9
Fraction Csp3 0.14
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 47.63
TPSA ?

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

89.6 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.59
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

1.54
Log Po/w (WLOGP)?

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

1.26
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.

0.6
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

1.78
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.35

Water Solubility

Log S (ESOL):?

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

-2.42
Solubility 0.685 mg/ml ; 0.00378 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.

-3.03
Solubility 0.169 mg/ml ; 0.000931 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

-2.78
Solubility 0.304 mg/ml ; 0.00167 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

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

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.

-6.31 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)

1.81

Application In Synthesis of [ 113713-60-3 ]

* 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 [ 113713-60-3 ]

[ 113713-60-3 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 75-15-0 ]
  • [ 28020-38-4 ]
  • [ 113713-60-3 ]
YieldReaction ConditionsOperation in experiment
0.187 g Compound 9c was obtained as described17 using 2,6-dichloropyridine as the starting material in five steps, including methoxylation, nitration, amination, reduction, and cyclization. The overall yield of this sequence was up to 45.7%. The structure of the product was identified by 1H NMR, MS, and IR. A solution of 0.5 g (3 mmol) 6-methoxy-3-nitropyridine-2-amine 100 ml CH3OH, 2 ml H2O, and 0.1 g Pd/C (10%) are allowed to shake with H2 (3 bar) in a hydrogenation apparatus until constant pressure. After filtration, the product solution is heated with 1 ml CS2 and 0.225 g KOH until reflux. When the reaction is completed (TLC control) the solvent is evaporated under reduced pressure. The resulted solid is recrystallized from ethanol. Yield: 0.187 g (1.1 mmol), 35%, mp: 223-225 C. IR: inlMMLBox (cm-1) = 3262; 3051; 1624. 1H NMR: (200 MHz, DMSO-d6) delta (ppm) = 12.99 (s, 1H, NH); 12.54 (s, 1H, NH); 7.43-7.47 (d, 1H, J = 8.5 Hz, H arom.); 6.55-6.60 (d, 1H, J = 8.5 Hz, H arom.); 3.83 (s, 3H, CH3). 13C NMR: (50 MHz, DMSO-d6) delta (ppm) = 167.60; 160.12; 143.62; 120.17; 119.65; 103.90; 53.49
16.9 g With potassium hydroxide; In ethanol; water; for 12.0h;Reflux; To a solution of compound 2 (20.56 g, 148 mmol) in a mixture of EtOH (200 mL) and water (40 mL) was added KOH (9.75 g, 148 mmol) and CS2 (22.5 g, 296 mmol). The reaction mixture was stirred at reflux for 12 h. The solvents were evaporated, and the residue was purified by column chromatography on silica gel with eluent (2:98 to 10:90 MeOH/CH2Cl2), affording a gray solid product 3 (16.9 g, 63%). Rf = 0.50 (1:19 MeOH/CH2Cl2), mp 246-248 C. 1H NMR (DMSO-d6): delta 3.83 (s, 3H, OCH3), 6.56 (d, J = 8.5 Hz, 1H, Ar-H), 7.44 (d, J = 8.5 Hz, 1H, Ar-H), 12.73 (s, 2H, NH). MS (ESI): 182 ([M+H]+, 100%); MS (ESI): 180 ([M-H]-, 23%).
  • 2
  • [ 113713-60-3 ]
  • [ 62593-78-6 ]
  • N-(3,4-dimethoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In ethanol; water; at 20℃; General procedure: To a solution of compound 3 (360 mg, 2.0 mmol) in a mixture of EtOH (60 mL) and 1 N aq NaOH (2.2 mL, 2.2 mmol), compound 1 (2.1 mmol) was added. The resulting reaction mixture was stirred overnight at rt. Then solvents were removed under reduced pressure, and the crude product was purified by column chromatography on silica gel with eluent (0:100 to 3:97 MeOH/CH2Cl2) to give a white solid product 4 (50-65% yields).
  • 4
  • [ 113713-60-3 ]
  • 2-chloro-N-(3-hydroxy-4-methoxyphenyl)acetamide [ No CAS ]
  • N-(3-hydroxy-4-methoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In ethanol; water; at 20℃; General procedure: To a solution of compound 3 (360 mg, 2.0 mmol) in a mixture of EtOH (60 mL) and 1 N aq NaOH (2.2 mL, 2.2 mmol), compound 1 (2.1 mmol) was added. The resulting reaction mixture was stirred overnight at rt. Then solvents were removed under reduced pressure, and the crude product was purified by column chromatography on silica gel with eluent (0:100 to 3:97 MeOH/CH2Cl2) to give a white solid product 4 (50-65% yields).
  • 5
  • [ 113713-60-3 ]
  • [ 17640-79-8 ]
  • N-(4-hydroxy-3-methoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In ethanol; water; at 20℃; General procedure: To a solution of compound 3 (360 mg, 2.0 mmol) in a mixture of EtOH (60 mL) and 1 N aq NaOH (2.2 mL, 2.2 mmol), compound 1 (2.1 mmol) was added. The resulting reaction mixture was stirred overnight at rt. Then solvents were removed under reduced pressure, and the crude product was purified by column chromatography on silica gel with eluent (0:100 to 3:97 MeOH/CH2Cl2) to give a white solid product 4 (50-65% yields).
  • 6
  • [ 113713-60-3 ]
  • [ 58915-18-7 ]
  • C17H16N4O4S [ No CAS ]
 

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Technical Information

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