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Chemical Structure| 37832-20-5 Chemical Structure| 37832-20-5

Structure of 37832-20-5

Chemical Structure| 37832-20-5

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Product Details of [ 37832-20-5 ]

CAS No. :37832-20-5
Formula : C6H8N2O
M.W : 124.14
SMILES Code : NOCC1=CC=CN=C1
MDL No. :MFCD13175304
InChI Key :TVPSRTVMZGECAT-UHFFFAOYSA-N
Pubchem ID :12213991

Safety of [ 37832-20-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H315-H319-H225
Precautionary Statements:P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P403+P235
Class:3
UN#:1993
Packing Group:

Computational Chemistry of [ 37832-20-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.17
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 33.0
TPSA ?

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

48.14 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.26
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

-0.23
Log Po/w (WLOGP)?

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

0.32
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.

-0.2
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

0.51
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.33

Water Solubility

Log S (ESOL):?

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

-0.83
Solubility 18.5 mg/ml ; 0.149 mol/l
Class?

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

Very soluble
Log S (Ali)?

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

-0.32
Solubility 58.9 mg/ml ; 0.475 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

-1.77
Solubility 2.12 mg/ml ; 0.0171 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

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.

-7.22 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)

1.58

Application In Synthesis of [ 37832-20-5 ]

* 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 [ 37832-20-5 ]

[ 37832-20-5 ] Synthesis Path-Downstream   1~9

YieldReaction ConditionsOperation in experiment
10% With N-hydroxyphthalimide; triphenylphosphine; diethylazodicarboxylate; In dichloromethane; at 20℃; General procedure: Alcohol (1.0 equiv.), N-hydroxypthalimide (1.1 equiv.) and triphenylphosphine (1.1 equiv.) were dissolved in dichioromethane (6 mE). Diethyl azodicarboxylate (DEAD) (1.1 equiv.) was added dropwise while stirring to the solution and the reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with dichloromethane (20 mE). The combined dichloromethane was washed with 10% NaOH (2x15 mE), water (2x15 mE) and brine (15 mE). The solvent was removed under reduced pressure and the crude product was used for the next step.The crude product was dissolved in ethanol (8 mE) and hydrazine monohydrate (2.0 equiv.) was added. The reaction was refluxed for 2 h and filtered. Ethanol was removed under reduced pressure. The crude product was purified by flash colunm chromatography on silica gel.
  • 2
  • [ 412293-43-7 ]
  • [ 37832-20-5 ]
  • [ 792913-89-4 ]
YieldReaction ConditionsOperation in experiment
In methanol; for 5.0h; To a stirred solution of tert-butyl 1-methyl-4-oxocyclohexylcarbamate obtained in Preparation 2-5 (L. OOg) in methanol (0.5mL), was added 3-[(aminooxy) methyl] pyridine obtained in Example 3-2 (552mg). The mixture was stirred for 5hrs. The solution was concentrated in vacuo. The residue was triturated with diisopropylether, then filtrated to provide the target compound (892mg) as a white solid. 1H-NMR (300MHZ, CDCL3) : No. 1. 35 (3H, s), 1.44 (9H, S), 1.45-1. 60 (2H, m), 2.05-2. 29 (5H, m), 2.81-2. 93 (1H, m), 4.40 (1H, br-s), 5.06 (2H, s), 7.27 (1H, dd, J=4.8, 7. 9HZ), 7.67 (1H, d, J=1.7, 7.9Hz), 8.54 (1H, dd, J=1.7, 5. 0Hz), 8.60 (1H, br-d, J=1. 7Hz). MS (ES+) : m/e 334.20.
  • 3
  • C34H56N2O11 [ No CAS ]
  • [ 37832-20-5 ]
  • C40H62N4O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With acetic acid; In ethanol; at 60℃; for 12.0h; Step 5b : Compound of formula I : A and B taken together with the carbon atom to which they are attached are C=N-O-CH2-(3-pyridyl), X and Y taken together with the carbon atom to which they are attached are C=N-Ac, L = CH2CH3, Z = H and R ?' = H; To a solution of N-phthaloyl-O-pyridin-3-ylmethyl-hydroxylamine (81.3 mg, 0.32 mmol) in 5 ml of ethanol was added hydrazine hydrate (12 mg, 0.24 mmol) at room temperature. The mixture was stirred at 40C for 2 hours and then cooled to room temperature. Acetic acid (7 tI, 0.12 mmol) was added followed by the compound of Example 3 (27 mg, 0.04 mmol). The mixture was stirred at 60 C for 12 hours. The solvent was removed under vacuum and the residue was purified by flash chromatography (SiO2, CH2CI2 : 2M ammonia in CH30H = 95: 5) to give the title compound (24 mg). MS (ES1) m/z 774.48 (M+H) +.
  • 4
  • [ 30777-95-8 ]
  • [ 37832-20-5 ]
YieldReaction ConditionsOperation in experiment
With hydrazine; In ethanol; at 20 - 40℃; for 2.0h; Step 5b : Compound of formula I : A and B taken together with the carbon atom to which they are attached are C=N-O-CH2-(3-pyridyl), X and Y taken together with the carbon atom to which they are attached are C=N-Ac, L = CH2CH3, Z = H and R ?' = H; To a solution of N-phthaloyl-O-pyridin-3-ylmethyl-hydroxylamine (81.3 mg, 0.32 mmol) in 5 ml of ethanol was added hydrazine hydrate (12 mg, 0.24 mmol) at room temperature. The mixture was stirred at 40C for 2 hours and then cooled to room temperature. Acetic acid (7 tI, 0.12 mmol) was added followed by the compound of Example 3 (27 mg, 0.04 mmol). The mixture was stirred at 60 C for 12 hours. The solvent was removed under vacuum and the residue was purified by flash chromatography (SiO2, CH2CI2 : 2M ammonia in CH30H = 95: 5) to give the title compound (24 mg). MS (ES1) m/z 774.48 (M+H) +.
  • 6
  • [ 37832-20-5 ]
  • [ 1980-14-9 ]
  • [ 1456520-56-1 ]
  • 8
  • [ 37832-20-5 ]
  • [ 533-67-5 ]
  • (3S,4R)-3,4,5-trihydroxypentanal O-pyridin-3-ylmethyl oxime [ No CAS ]
  • (3S,4R)-3,4,5-trihydroxypentanal O-pyridin-3-ylmethyl oxime [ No CAS ]
  • 9
  • [ 37832-20-5 ]
  • [13C5]-2-deoxy-D-ribose [ No CAS ]
  • C6(13)C5H16N2O4 [ No CAS ]
 

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