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Chemical Structure| 51677-09-9

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Product Details of [ 51677-09-9 ]

CAS No. :51677-09-9
Formula : C11H9NO3
M.W : 203.19
SMILES Code : O=C(C1=NOC(C2=CC=CC=C2)=C1)OC
MDL No. :MFCD02159553
InChI Key :XMPLCJOQBDGMKT-UHFFFAOYSA-N
Pubchem ID :905953

Safety of [ 51677-09-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 51677-09-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 11
Fraction Csp3 0.09
Num. rotatable bonds 3
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 53.22
TPSA ?

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

52.33 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.29
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

2.76
Log Po/w (WLOGP)?

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

2.13
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.

1.33
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

2.27
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.15

Water Solubility

Log S (ESOL):?

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

-3.18
Solubility 0.133 mg/ml ; 0.000656 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.

-3.51
Solubility 0.0622 mg/ml ; 0.000306 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

-3.84
Solubility 0.0295 mg/ml ; 0.000145 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

Yes
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.

-5.58 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

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)

2.76

Application In Synthesis of [ 51677-09-9 ]

* 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 [ 51677-09-9 ]

[ 51677-09-9 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 20577-73-5 ]
  • [ 51677-09-9 ]
References: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 13, p. 2390 - 2410.
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 18, p. 8337 - 8352.
[3] Journal of Molecular Structure, 2009, vol. 919, # 1-3, p. 47 - 53.
[4] Indian Journal of Heterocyclic Chemistry, 2011, vol. 20, # 3, p. 279 - 280.
[5] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 6, p. 1097 - 1102.
[6] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 9, p. 1369 - 1375.
[7] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 273 - 280.
[8] Indian Journal of Heterocyclic Chemistry, 2012, vol. 22, # 1, p. 27 - 30.
  • 2
  • [ 1313396-20-1 ]
  • [ 51677-09-9 ]
YieldReaction ConditionsOperation in experiment
81% With silver tetrafluoroborate; phenol In tetrahydrofuran for 12 h; Reflux General procedure: To a solution of alkynyl oxime ether 1 (0.15 mmol) in THF (5 mL) were added phenol (28 mg, 0.3 mmol) and AgBF4 (5.8 mg, 0.03 mmol), with a drying tube filled with silica gel at room temperature. After being stirred at reflux for 1-12 h (TLC monitoring), the reaction mixture was concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/AcOEt=3-10:1) to afford isoxazole 3. The physical and spectroscopic data of 3a5 and 3j12h were in accord with those reported in the literature.
References: [1] Tetrahedron, 2011, vol. 67, # 25, p. 4612 - 4615.
  • 3
  • [ 30673-27-9 ]
  • [ 536-74-3 ]
  • [ 51677-09-9 ]
YieldReaction ConditionsOperation in experiment
31% With triethylamine In diethyl ether at 20℃; for 9.5 h; Inert atmosphere To a stirred solution of methyl chlorooximidoacetate (235 mg, 1.71 mmol) and phenylacetylene (0.38 mL, 3.42 mmol) in Et2O (8.55 mL) was added Et3N (0.47 mL, 3.42 mmol) at rt under N2 and the resultingsolution was stirred for 9.5 h. Sat. NH4Cl aq. was added to the reaction mixture and the resultingsolution was extracted with AcOEt. The combined organic layer was dried over Na2SO4 andconcentrated in vacuo. The crude product was purified by flash column chromatography on silica gel(hexane/AcOEt = 5/1). The product was obtained as pale yellow oil (108 mg, 31percent);
References: [1] Tetrahedron Letters, 2012, vol. 53, # 29, p. 3746 - 3749.
  • 4
  • [ 14441-90-8 ]
  • [ 18107-18-1 ]
  • [ 51677-09-9 ]
References: [1] Patent: WO2010/85581, 2010, A1, . Location in patent: Page/Page column 82.
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2820 - 2840.
  • 5
  • [ 5437-67-2 ]
  • [ 536-74-3 ]
  • [ 51677-09-9 ]
References: [1] Bulletin of the Chemical Society of Japan, 1985, vol. 58, # 9, p. 2519 - 2522.
  • 6
  • [ 2483-57-0 ]
  • [ 536-74-3 ]
  • [ 51677-09-9 ]
References: [1] Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 9, p. 2827 - 2832.
  • 7
  • [ 98-86-2 ]
  • [ 51677-09-9 ]
References: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 9, p. 1369 - 1375.
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 273 - 280.
[3] Indian Journal of Heterocyclic Chemistry, 2012, vol. 22, # 1, p. 27 - 30.
[4] Journal of Medicinal Chemistry, 2018, vol. 61, # 18, p. 8337 - 8352.
  • 8
  • [ 67-56-1 ]
  • [ 14441-90-8 ]
  • [ 51677-09-9 ]
References: [1] Synthesis (Germany), 2013, vol. 45, # 2, p. 260 - 264.
  • 9
  • [ 2687-43-6 ]
  • [ 51677-09-9 ]
References: [1] Tetrahedron, 2011, vol. 67, # 25, p. 4612 - 4615.
  • 10
  • [ 20577-73-5 ]
  • [ 51677-09-9 ]
References: [1] Archiv der Pharmazie, 1995, vol. 328, # 5, p. 437 - 443.
  • 11
  • [ 41158-32-1 ]
  • [ 51677-09-9 ]
References: [1] Journal of the Chemical Society, 1950, p. 236,240.
 

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