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Structure of 50501-38-7

Chemical Structure| 50501-38-7

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Product Details of [ 50501-38-7 ]

CAS No. :50501-38-7
Formula : C7H6N2O
M.W : 134.14
SMILES Code : N#CC1=NC(CO)=CC=C1
MDL No. :MFCD07367926
InChI Key :VNXYECKZHAPGDI-UHFFFAOYSA-N
Pubchem ID :14761458

Safety of [ 50501-38-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P280-P305+P351+P338-P310

Computational Chemistry of [ 50501-38-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 35.08
TPSA ?

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

56.91 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.29
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

-0.41
Log Po/w (WLOGP)?

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

0.29
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.

-0.75
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

1.15
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.31

Water Solubility

Log S (ESOL):?

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

-0.79
Solubility 21.7 mg/ml ; 0.162 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 64.1 mg/ml ; 0.478 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

-1.91
Solubility 1.66 mg/ml ; 0.0124 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.

-7.41 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

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)

1.68

Application In Synthesis of [ 50501-38-7 ]

* 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.

  • Upstream synthesis route of [ 50501-38-7 ]

[ 50501-38-7 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 39621-11-9 ]
  • [ 50501-38-7 ]
YieldReaction ConditionsOperation in experiment
61% With hydroxylamine hydrochloride In dimethyl sulfoxide at 100℃; for 2 h; Inert atmosphere P3: For alternative syntheses, see [35–37]. The reaction was performed under nitrogen. Hydroxylamine hydrochloride (600 mg,8.63 mmol; excess) and P1 (750 mg, 5.47 mmol) were stirred in DMSO (3 mL; 99.7percent, degassed, extra dry, over mol. sieve, water<50 ppm, Acros) at 100°C (bath temperature) for 2 h to give dark red solution. It was extracted with CH2Cl2 and sat. aq. solution of NaCl. The organic layer was extracted with sat. aq. solution of NaCl to remove the residual DMSO. The aqueous extracts were back extracted with CH2Cl2. The aim of the extraction is to remove DMSO without losing the product (it is soluble in water). The combined organic extracts were evaporated and purified by chromatography on silica (20 g) with CH2Cl2 to remove the impurities and with 0.5percentCH3OH in CH2Cl2 to recover the product. Pale yellow solid: 446 mg(3.32 mmol; 61percent; C7H6N2O; MW 134.14).
References: [1] Inorganica Chimica Acta, 2015, vol. 427, p. 81 - 86.
  • 2
  • [ 50501-37-6 ]
  • [ 50501-38-7 ]
References: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458.
[2] Russian Journal of Organic Chemistry, 2017, vol. 53, # 7, p. 963 - 970[3] Zh. Org. Khim., 2017, vol. 53, # 7, p. 951 - 958,8.
[4] Patent: WO2006/21801, 2006, A1, . Location in patent: Page/Page column 44-45.
  • 3
  • [ 85148-95-4 ]
  • [ 50501-38-7 ]
References: [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 8, p. 3130 - 3141.
  • 4
  • [ 1620-75-3 ]
  • [ 50501-38-7 ]
References: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458.
[2] Russian Journal of Organic Chemistry, 2017, vol. 53, # 7, p. 963 - 970[3] Zh. Org. Khim., 2017, vol. 53, # 7, p. 951 - 958,8.
  • 5
  • [ 586-98-1 ]
  • [ 50501-38-7 ]
References: [1] Tetrahedron Asymmetry, 1998, vol. 9, # 19, p. 3437 - 3443.
[2] Tetrahedron Asymmetry, 1998, vol. 9, # 19, p. 3437 - 3443.
  • 6
  • [ 931-19-1 ]
  • [ 50501-38-7 ]
References: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458.
  • 7
  • [ 25813-90-5 ]
  • [ 50501-38-7 ]
References: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458.
  • 8
  • [ 92304-51-3 ]
  • [ 50501-38-7 ]
References: [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458.
  • 9
  • [ 10242-36-1 ]
  • [ 50501-38-7 ]
References: [1] Tetrahedron Asymmetry, 1998, vol. 9, # 19, p. 3437 - 3443.
  • 10
  • [ 104508-24-9 ]
  • [ 50501-38-7 ]
References: [1] Russian Journal of Organic Chemistry, 2017, vol. 53, # 7, p. 963 - 970[2] Zh. Org. Khim., 2017, vol. 53, # 7, p. 951 - 958,8.
  • 11
  • [ 10242-36-1 ]
  • [ 7677-24-9 ]
  • [ 50501-38-7 ]
References: [1] Tetrahedron Asymmetry, 1998, vol. 9, # 19, p. 3437 - 3443.
 

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