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Structure of 163395-24-2

Chemical Structure| 163395-24-2

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Product Details of [ 163395-24-2 ]

CAS No. :163395-24-2
Formula : C8H6FNO4
M.W : 199.14
SMILES Code : OC(=O)CC1=CC(F)=C(C=C1)[N+]([O-])=O
MDL No. :MFCD03094239
InChI Key :BRWLAOKLDCMHIC-UHFFFAOYSA-N
Pubchem ID :2774665

Safety of [ 163395-24-2 ]

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

Computational Chemistry of [ 163395-24-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 3
Num. H-bond acceptors 5.0
Num. H-bond donors 1.0
Molar Refractivity 46.77
TPSA ?

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

83.12 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.9
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

1.31
Log Po/w (WLOGP)?

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

1.78
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.

1.0
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

-0.15
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.97

Water Solubility

Log S (ESOL):?

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

-2.02
Solubility 1.91 mg/ml ; 0.00957 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.

-2.66
Solubility 0.44 mg/ml ; 0.00221 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

-1.84
Solubility 2.87 mg/ml ; 0.0144 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.

-6.58 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

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.56

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

2.0 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)

1.78

Application In Synthesis of [ 163395-24-2 ]

* 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 [ 163395-24-2 ]

[ 163395-24-2 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 147949-76-6 ]
  • [ 163395-24-2 ]
  • [ 163395-22-0 ]
  • 3
  • 2-Amino-N-(3-hydroxy-benzyl)-acetamide; compound with trifluoro-acetic acid [ No CAS ]
  • [ 163395-24-2 ]
  • [ 163395-22-0 ]
  • 4
  • [ 169339-41-7 ]
  • [ 163395-24-2 ]
  • 5
  • [ 29022-11-5 ]
  • [ 112883-29-1 ]
  • [ 163395-24-2 ]
  • (S)-4-Nitro-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3,5,7(21),16(20),17-hexaene-14-carboxylic acid amide [ No CAS ]
  • 6
  • [ 112883-29-1 ]
  • [ 132388-59-1 ]
  • [ 163395-24-2 ]
  • (11S,14S)-11-Carbamoylmethyl-4-nitro-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3,5,7(21),16(20),17-hexaene-14-carboxylic acid amide [ No CAS ]
  • 7
  • [ 163395-24-2 ]
  • C48H47N7O15 [ No CAS ]
  • C56H51FN8O18 [ No CAS ]
  • 8
  • [ 163395-24-2 ]
  • C33H27N5O10 [ No CAS ]
  • 9
  • [ 64123-77-9 ]
  • [ 163395-24-2 ]
  • 10
  • [ 163395-24-2 ]
  • [ 163395-21-9 ]
  • 11
  • [ 163395-24-2 ]
  • 18-Amino-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]icosa-1(19),3(20),4,6,15,17-hexaene-10,13-dione [ No CAS ]
  • 12
  • [ 331-25-9 ]
  • [ 163395-24-2 ]
YieldReaction ConditionsOperation in experiment
65% With sulfuric acid; nitric acid; at 0 - 20℃; for 3.5h; To a solution of nitric acid (1.6 mL) was added a solution of 2-(3-fluorophenyl)acetic acid (6 g, 38.93 mmol) in sulfuric acid (12 mL) dropwise with stirring at 0 C in 30 mm. The resulting solution was stirred for 3 h at room temperature and then water/ice was added. The resulting solution was extracted with of ethyl acetate and the organic layers combined and driedover anhydrous Na2504 and concentrated. The residue was purified by chromatography (ethylacetate/petroleum ether (1:3)) to afford 5 g (65%) of 2-(3-fluoro-4-nitrophenyl)acetic acid as ayellow solid.
  • 13
  • [ 163395-24-2 ]
  • 2-(3-fluoro-4-nitrophenyl)ethan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (methylsulfanyl)methane borane; In tetrahydrofuran; at 0 - 60℃; for 2.0h; To a solution of 2-(3 -fluoro-4-nitrophenyl)acetic acid (5 g, 25.11 mmol) in THF (150mL) was added (methylsulfanyl)methane borane (5 mL) dropwise with stirring at 0 C. Theresulting solution was stirred for 2 h at 60 C and then concentrated. The reaction was then quenched by the addition of NH4C1(aq). The resulting solution was extracted with of ethyl acetate and the organic layers combined and dried over anhydrous Na2504 and concentrated to afford 5 g (crude) of 2-(3-fluoro-4-nitrophenyl)ethan-1-ol as yellow oil.
  • 14
  • [ 163395-24-2 ]
  • (4-amino-3-fluorophenyl)ethan-1-ol [ No CAS ]
  • 15
  • [ 163395-24-2 ]
  • tert-butyl N-[2-fluoro-4-(2-hydroxyethyl)phenyl]carbamate [ No CAS ]
  • 16
  • [ 163395-24-2 ]
  • tert-butyl N-[2-fluoro-4-(2-iodoethyl)phenyl]carbamate [ No CAS ]
  • 17
  • [ 67-56-1 ]
  • [ 163395-24-2 ]
  • [ 169339-41-7 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; at 25℃; for 1.5h; Add <strong>[163395-24-2]2-(3-fluoro-4-nitrophenyl)acetic acid</strong> (1.00 g, 5.00 mmol), methanol (10 mL), and dichlorosulfoxide (1.19 g, 10.0 mmol) to a 25 mL vial at 25 C. Stir for 1.5 hours. Thin layer chromatography analysis detected the disappearance of the raw materials. Concentration gave the title compound.
  • 18
  • [ 163395-24-2 ]
  • 1-morpholino-2-(4-nitro-3-(piperidin-1-yl)phenyl)ethan-1-one [ No CAS ]
  • 19
  • [ 163395-24-2 ]
  • 4-(4-nitro-3-(piperidin-1-yl)phenethyl)morpholine [ No CAS ]
  • 20
  • [ 110-91-8 ]
  • [ 163395-24-2 ]
  • 2-(3-fluoro-4-nitrophenyl)-1-morpholinoethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 20℃; for 23.0h; To a CH2Cl2 (10 mL) solution of <strong>[163395-24-2]2-(3-fluoro-4-nitrophenyl)acetic acid</strong> (995.7 mg, 5 mmol) and morpholine (454 muL, 5.25 mmol), HATU (2.09 g, 5.5 mmol) and NaHCO3 (504 mg, 6 mmol) were added, and the solution was stirred at room temperature. Additional morpholine (0.2 mL) was added at 16 hours, 19 hours and 20 hours. At 23 hours, the reaction went to completion as monitored by LC-MS. Solvent was removed by rotary evaporation under reduced pressure, and the product was purified by silica gel column chromatography. Compound 2-(3-fluoro-4-nitrophenyl)-1-morpholinoethan-1-one was obtained as a light yellow oil and was used without further purification: 1H NMR (300 MHz, Chloroform-d) delta 8.05 (dd, J=8.1, 8.1 Hz, 1H), 7.24-7.15 (m, 2H), 3.77 (s, 2H), 3.71-3.63 (m, 6H), 3.50-3.47 (m, 2H); LRMS (M+H) m/z 269.50.
  • 21
  • [ 163395-24-2 ]
  • 2-(4-amino-3-(piperidin-1-yl)phenyl)-1-morpholinoethan-1-one dihydrogen chloride [ No CAS ]
  • 22
  • [ 163395-24-2 ]
  • 4-(2-morpholinoethyl)-2-(piperidin-1-yl)aniline trihydrogen chloride [ No CAS ]
 

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