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Chemical Structure| 38533-61-8 Chemical Structure| 38533-61-8

Structure of 38533-61-8

Chemical Structure| 38533-61-8

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Product Details of [ 38533-61-8 ]

CAS No. :38533-61-8
Formula : C6H5ClN2O3
M.W : 188.57
SMILES Code : C1=C(C(=NC(=C1)OC)Cl)[N+](=O)[O-]
MDL No. :MFCD00130268
InChI Key :DVRGUTNVDGIKTP-UHFFFAOYSA-N
Pubchem ID :2795029

Safety of [ 38533-61-8 ]

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

Computational Chemistry of [ 38533-61-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.17
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 44.56
TPSA ?

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

67.94 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.47
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

1.95
Log Po/w (WLOGP)?

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

1.65
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.

0.06
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

-0.13
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.

-2.48
Solubility 0.631 mg/ml ; 0.00334 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.

-3.0
Solubility 0.188 mg/ml ; 0.000997 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

-2.15
Solubility 1.33 mg/ml ; 0.00705 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

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.

-6.07 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

3.0 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)

2.03

Application In Synthesis of [ 38533-61-8 ]

* 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 [ 38533-61-8 ]

[ 38533-61-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 3325-11-9 ]
  • [ 38533-61-8 ]
  • N-(6-methoxy-3-nitropyridin-2-yl)-1H-benzo[d][1,2,3]triazol-5-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With trimethylamine; In methanol; at 120℃; for 24h; 2-Chloro-6-methoxy-3-nitropyridine (0.13 g, 0.69 mmol)5-Amino-1H-benzotriazole (0.09 g, 0.69 mmol) and triethylamine (0.11 mL, 0.76 mmol) were dissolved in methanol and the mixture was stirred at 120 ° C for 24 hours. After cooling in the atmosphere, water was added slowly and stirred for 30 minutes. The resulting solid product was filtered off, washed with methanol and dried to give compound 5e (61percent yield).
  • 2
  • [ 109-11-5 ]
  • [ 38533-61-8 ]
  • 4-(6-methoxy-3-nitropyridin-2-yl)morpholin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 100℃; for 2h;Inert atmosphere; A mixture of 2-chloro-6-methoxy-3-nitropyridine (1.89 g, 10 mmol), <strong>[109-11-5]morpholin-3-one</strong> (1.01 g, 10 mmol), Xantphos (578 mg, 1.0 mmol), Pd2(dba)3 (457 mg, 0.5 mmol), Cs2CO3 (6.5 g, 20 mmol), in 1,4-dioxane (50 mL) was stirred under nitrogen at 100 C for 2h. The mixture was then cooled to room temperature and filtered through Celite. The filtrate was concentrated and purified by flash chromatography (3:1 petroleum ether:ethyl acetate) to afford 4-(6- methoxy-3-nitropyridin-2-yl)<strong>[109-11-5]morpholin-3-one</strong> (1.2 g, yield 47%) as a yellow solid. LCMS (ESI) [M+H] = 254.2.
  • 3
  • [ 38533-61-8 ]
  • [ 14752-66-0 ]
  • 2-((4-chlorophenyl)sulfonyl)-6-methoxy-3-nitropyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
81.21% With hydrogenchloride; tetrabutyl-ammonium chloride; In N,N-dimethyl acetamide; water; at 80℃; for 1h; To a stirred solution of 6-methoxy-2-chloro-3-nitro pyridine(1 ; 5.0 g, 26.596 mmol) in dimethyl acetamide (75ml_) was added sodium 4-chlorobenzene-sulphinate (2;7.92g, 39.894 mmol) and tetra-N-butylammonium chloride (2.22g, 7.979 mmol) and Cone HCI 0.75 ml at room temperature. The reaction mixture was stirred at 80C for 1 hour. Progress of reaction was monitored by LCMS. The whole reaction mixture was poured on crushed ice to get solid. This solid compound was filtered through sintered funnel and thoroughly dried under vacuum to isolate 2-((4-Chlorophenyl)sulfonyl)-6-methoxy- 3-nitropyridine as desired product (7.1 g, 81.21 %). 1H NMR (400 MHz, CDCI3) d 8.10 (d, J= 8.6 Hz, 1 H), 8.0 (d, J= 7.9 Hz, 2H), 7.56 (d, J= 7.9 Hz, 2H), 6.95 (d, J= 8.7 Hz, (1079) 1 H), 3.69 (s, 3H). LCMS [m/z (M+H)+ =(Calculated for C12H9N205SCI+H: 329) found: 329], Purity at l=220hht 98.73%
 

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Technical Information

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