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Structure of 2243-58-5

Chemical Structure| 2243-58-5

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Product Details of [ 2243-58-5 ]

CAS No. :2243-58-5
Formula : C10H11ClN2
M.W : 194.66
SMILES Code : NNC1=CC=C2C=CC=CC2=C1.[H]Cl
MDL No. :MFCD04109481
InChI Key :OXOQKRNEPBHINU-UHFFFAOYSA-N
Pubchem ID :519950

Safety of [ 2243-58-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P305+P351+P338

Computational Chemistry of [ 2243-58-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 10
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 2.0
Molar Refractivity 58.12
TPSA ?

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

38.05 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

2.88
Log Po/w (WLOGP)?

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

2.74
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.

2.72
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

1.47
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.96

Water Solubility

Log S (ESOL):?

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

-3.36
Solubility 0.0841 mg/ml ; 0.000432 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.

-3.34
Solubility 0.0892 mg/ml ; 0.000458 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

-3.75
Solubility 0.0345 mg/ml ; 0.000177 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

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.

-5.44 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)

1.38

Application In Synthesis of [ 2243-58-5 ]

* 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 [ 2243-58-5 ]

[ 2243-58-5 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 120-57-0 ]
  • [ 2243-58-5 ]
  • piperonal-[2]naphthylhydrazone [ No CAS ]
  • 2
  • [ 2001-23-2 ]
  • [ 2243-58-5 ]
  • 2-biphenyl-4-yl-1-phenyl-3<i>H</i>-benz[<i>e</i>]indole [ No CAS ]
  • 3
  • [ 24623-20-9 ]
  • [ 2243-58-5 ]
  • [ 63039-86-1 ]
  • 4
  • [ 14548-38-0 ]
  • [ 2243-58-5 ]
  • [ 121936-93-4 ]
  • 5
  • [ 40353-34-2 ]
  • [ 2243-58-5 ]
  • 9-nitro-7<i>H</i>-dibenzo[<i>a,g</i>]carbazole [ No CAS ]
  • 6
  • [ 5398-10-7 ]
  • [ 2243-58-5 ]
  • 4-hexyl-1-[2]naphthyl-pyrazolidine-3,5-dione [ No CAS ]
  • 7
  • [ 420-04-2 ]
  • [ 2243-58-5 ]
  • [2]naphthylamino-guanidine; hydrochloride [ No CAS ]
  • 8
  • [ 692-29-5 ]
  • [ 2243-58-5 ]
  • (3<i>H</i>-benz[<i>e</i>]indol-1-yl)-acetic acid ethyl ester [ No CAS ]
  • 9
  • [ 692-29-5 ]
  • [ 2243-58-5 ]
  • 3-(2-acetylamino-[1]naphthyl)-4-imino-butyric acid [ No CAS ]
  • 10
  • [ 600-35-1 ]
  • [ 2243-58-5 ]
  • 3-[2]naphthylhydrazono-2-oxo-propionic acid-(<i>N</i>-[2]naphthyl-hydrazide) [ No CAS ]
  • 11
  • [ 607-83-0 ]
  • [ 2243-58-5 ]
  • 4-heptyl-1-[2]naphthyl-pyrazolidine-3,5-dione [ No CAS ]
  • 12
  • [ 1009-14-9 ]
  • [ 2243-58-5 ]
  • 2-phenyl-1-propyl-3<i>H</i>-benz[<i>e</i>]indole [ No CAS ]
  • 13
  • [ 22009-37-6 ]
  • [ 2243-58-5 ]
  • [ 63039-88-3 ]
  • 14
  • [ 5037-63-8 ]
  • [ 2243-58-5 ]
  • 8,11-dimethyl-12,13-dihydro-7<i>H</i>-dibenzo[<i>a,g</i>]carbazole [ No CAS ]
  • 15
  • [ 22583-68-2 ]
  • [ 2243-58-5 ]
  • 9-<i>tert</i>-butyl-12,13-dihydro-7<i>H</i>-dibenzo[<i>a,g</i>]carbazole [ No CAS ]
  • 16
  • [ 26673-32-5 ]
  • [ 2243-58-5 ]
  • 9-chloro-12,13-dihydro-7<i>H</i>-dibenzo[<i>a,g</i>]carbazole [ No CAS ]
  • 17
  • [ 13621-25-5 ]
  • [ 2243-58-5 ]
  • [ 667914-67-2 ]
  • 18
  • [ 614-28-8 ]
  • [ 2243-58-5 ]
  • 1-[2]naphthyl-3,5-diphenyl-1<i>H</i>-[1,2,4]triazole [ No CAS ]
  • 19
  • [ 29431-37-6 ]
  • [ 2243-58-5 ]
  • 7,8,10,11-tetrahydro-benzo[<i>e</i>]thiopyrano[3,4-<i>b</i>]indole 9,9-dioxide [ No CAS ]
  • 21
  • [ 16676-29-2 ]
  • [ 2243-58-5 ]
  • [ 126642-60-2 ]
  • 23
  • [ 2243-58-5 ]
  • 1-(5-<i>tert</i>-butyl-2-naphthalen-2-yl-2<i>H</i>-pyrazol-3-yl)-3-phenyl-urea [ No CAS ]
  • 25
  • [ 2243-58-5 ]
  • [ 117043-89-7 ]
  • 27
  • [ 2243-58-5 ]
  • [ 29103-83-1 ]
  • 28
  • [ 2243-58-5 ]
  • [ 111355-28-3 ]
  • 29
  • [ 2243-58-5 ]
  • [ 1203-55-0 ]
  • 30
  • [ 2243-58-5 ]
  • [ 172168-01-3 ]
  • [ 907190-28-7 ]
YieldReaction ConditionsOperation in experiment
54% A mixture of ethyl 3-(3,5-dichlorophenyl)-3-oxopropanoate (500 mg, 1.9 mmol), <strong>[2243-58-5]2-naphthylhydrazine hydrochloride</strong> (372 mg, 1.9 mmol) and glacial acetic acid (19 ml) was refuxed overnight and cooled to room temperature. Mixture was taken to pH 6 using 1.0N aqueous sodium hydroxide and then extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated. The crude material was purified by flash chromatography on silica gel ( 0-65% ethyl acetate/hexanes) to give 5-(3,5-dichlorophenyl)-2-(2- naphthyl)-2,4-dihydro-3 H-pyrazol-3-one as a brown solid (365 mg, 54%). A mixture of 5-(3,5- dichlorophenyl)-2-(2-naphthyl)-2,4-dihydro-3 H-pyrazol-3-one (360 mg, 1.0 mmol), phosphorous tribromide (3.0 ml, 32 mmol) and anhydrous acetonitrile (1.0 ml) was placed in a Smith microwavable vial and heated in the Smith microwave apparatus for two minutes at 1000C to make mixture homogeneous, then heated to 15O0C until no starting material was observed by tic. The reaction usually was completed in forty minutes. The mixture was carefully poured into ice and stirred at room temperature. Extracted mixture with ethyl acetate, dried over sodium sulfate, filtered and concentrated to give 5-bromo-3-(3,5-dichlorophenyl)-l-(2-naphthyl)-l H-pyrazole as a brown solid (425 mg, 100%). A mixture of 5-bromo-3-(3,5-dichlorophenyl)-l-(2-naphthyl)-l H-pyrazole (441mg, 1.1 mmol), 3-buryn-l- ol (0.24 ml, 3.14 mmol), degassed triethylamine (10.2 ml), palladium tetrakistriphenylphosphine (194 mg, 0.17 mmol) and copper (I)bromide dimethyl sulfide (65 mg, 0.32 mmol) was heated to 7O0C for a few hours until no starting material was observed by tic. Mixture was cooled, concentrated, washed with brine and extracted with ethyl acetate. Organic extracts were combined, dried over sodium sulfate, filtered and concentrated to give a crude material which was further purified via flash chromatography on silica gel (0-75% ethyl acetate/hexanes). This afforded 4-[3-(3,5-dichlorophenyl)-l-Hpyrazol-5-yl]but-3-yn-l- ol as a tan solid (318 mg, 74%). 4-[3-(3,5-Dichlorophenyl)-l-Hpyrazol-5-yl]but-3-yn-l-ol (318 mg, 0.8 mmol), 5% platinum on carbon (200 mg) and ethyl acetate (20 ml) was stirred under hydrogen EPO <DP n="26"/>atmosphere at one atmosphere of pressure overnight. The mixture was filtered through a celite pad, washing with ethyl acetate and the filtrate concentrated to give 4-[3-(3,5-dichlorophenyl)-l-(2-naphthyl)- 1 H-pyrazol-5-yl]butan-l-ol as a white solid (255 mg, 80%). A mixture of 4-[3-(3,5-dichlorophenyl)-l-(2- naphthyl)-l H-pyrazol-5-yl]butan-l-ol (255 mg, 0.62 mmol), pyridinium dichromate (816 mg, 2.17 mmol) and dimethylformamide (3.1 ml) was stirred at room temperature overnight. Purification of the reaction mixture via flash chromatography on silica gel (0-40% ethyl acetate/hexanes) afforded 4-[3- (3,5-dichlorophenyl)-l-(2-naphthyl)-l Hpyrazol-5-yl]butanoic acid as a white solid (159 mg, 60%). MS (ESI) 426 (M+).
  • 31
  • [ 69316-09-2 ]
  • [ 2243-58-5 ]
  • [ 907190-89-0 ]
YieldReaction ConditionsOperation in experiment
The mixture of <strong>[2243-58-5]2-naphthylhydrazine hydrochloride</strong> (1.81g, 9.33mmol), 3-(3,5-dichlorophenyl)-3- oxopropanenitrile (2.44g, 11.45mmol) in 50ml toluene was heated to 13O0C for 12 hours. The reaction mixture was quenched with aqueous sodium bicarbonate (10OmL), extracted with EtOAc (3 x 10OmL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SC^ and concentrated in vacuo. The crude purified by liquid chromatography on silica gel using an ISCO single channel system (Etaexane/EtOAc: 10/0 to 1/9) to give 3-(3,5-dichlorophenyl)-l-(2-naphthyl)-lH-pyrazol- 5-amine as product. 1H NMR (CD3Cl3, 500 MHz) delta 8.055-8.051 (d, IH), 8.00-7.98 (d, IH), 7.90-7.88 EPO <DP n="42"/>(m, 2H), 7.78-7.60 (dd, IH), 7.726-7.722 (m, 2H), 7.57-7.53 (m, 2H), 7.29-7.28 (t, IH), 5.96 (s, IH), 3.95 (s, 2H). MS (ESI) 353.97 (M+-I-H).
  • 32
  • [ 113-24-6 ]
  • [ 2243-58-5 ]
  • [ 42178-83-6 ]
  • 33
  • [ 1271-55-2 ]
  • [ 2243-58-5 ]
  • [ 68-12-2 ]
  • [ 1259930-40-9 ]
  • 34
  • [ 453-72-5 ]
  • [ 2243-58-5 ]
  • [ 945528-20-1 ]
 

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