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Chemical Structure| 83-01-2 Chemical Structure| 83-01-2

Structure of 83-01-2

Chemical Structure| 83-01-2

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Product Details of [ 83-01-2 ]

CAS No. :83-01-2
Formula : C13H10ClNO
M.W : 231.68
SMILES Code : O=C(Cl)N(C1=CC=CC=C1)C2=CC=CC=C2
MDL No. :MFCD00000633
InChI Key :XNBKKRFABABBPM-UHFFFAOYSA-N
Pubchem ID :65741

Safety of [ 83-01-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314-H317
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:3261
Packing Group:

Computational Chemistry of [ 83-01-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 16
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 3
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 66.27
TPSA ?

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

20.31 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.58
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

3.08
Log Po/w (WLOGP)?

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

4.18
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.

3.68
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

2.65
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.24

Water Solubility

Log S (ESOL):?

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

-3.57
Solubility 0.0618 mg/ml ; 0.000267 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.

-3.17
Solubility 0.155 mg/ml ; 0.00067 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

-4.82
Solubility 0.00349 mg/ml ; 0.0000151 mol/l
Class?

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

Moderately 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

Yes
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.

-5.53 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

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)

1.98

Application In Synthesis of [ 83-01-2 ]

* 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 [ 83-01-2 ]

[ 83-01-2 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 136-77-6 ]
  • [ 83-01-2 ]
  • 2,4-bis-diphenylcarbamoyloxy-1-hexyl-benzene [ No CAS ]
  • 2
  • [ 6358-77-6 ]
  • [ 83-01-2 ]
  • <i>N</i>'-(5-bromo-2-methoxy-phenyl)-<i>N</i>,<i>N</i>-diphenyl-urea [ No CAS ]
  • 3
  • [ 83-01-2 ]
  • [ 3056-33-5 ]
  • [ 112233-74-6 ]
YieldReaction ConditionsOperation in experiment
[0100] A suspension of (5 g, 33 mmol) of guanine in 100 N-methy-2-pyrrolidinone NMP) and 20 ml acetic anhydride was heated to 150 C. for 3 hrs. The clear solution was stirred at room temperature for 24 hours. The precipitate was collected by filtration and washed with acetone. The N9,N2-diacetylated guanine (9) was dried and identified by 1H-NMR. [0101] M.P.=Decomp. 270 C. [0102] 1H-NMR (DMSO-d6): [0103] 12.1(bs, 1H-(N)), 8.53(s, 1H, H-(C8)); 2.91(s, 3H, Ac-(N9)); 2.31(s, 3H, -(N2-COCH3)). [0104] (5 g, 21.25 mmol) of (9) were suspended in 100 ml of dry pyridine and excess of diisopropyl ethylamine (DIEA). Then (5.91 g, 25.51 mmol) of diphenylcarbamoyl chloride ere added in portions. The reaction mixture turned orange immediately. Stirring continued for 2 hrs at r.t. then 20 nml if ice-cold water were added. The mixture was stirred for 10 minutes more and solvent was removed under reduced pressure. 100 ml of ethanol and 100 nml of water were added and the mixture was reflexed for 1.5 hr. After cooling to the room temperature, vigorous stirring continued for over night. The desired product (10) was collected by filtration and washed with 50 ml of ethanol, dried and characterized. [0105] M.P.=185 C. [0106] 1H-NMR (DMSO-d6): [0107] 10.7(s, 1H, H-(N2)); 8.55(s, 1H, H-(C8)); 7.61-7.38(m , 10H, aromatic); 2.28(s, 3H, -COCH3).
  • 4
  • [ 33893-89-9 ]
  • [ 83-01-2 ]
  • [ 1415251-76-1 ]
YieldReaction ConditionsOperation in experiment
90% With pyridine;Inert atmosphere; Reflux; The reaction was performed with 5-(2'-pyridyl)-1H-tetrazole (437 mg, 2.97 mmol) and diphenylcarbamoyl chloride (693 mg, 2.99 mmol, AlfaAesar) in pyridine (3 mL). The reaction mixture on cooling to RT gave suspension. It was diluted with solution of Na2CO3 (sat. aq.) and extracted with CH2Cl2. The organic layer was washed with water and evaporated. Purification by column chromatography was performed on silica (15 g). Elution with CH2Cl2 removed yellow impurity. Elution with 0.5-1.0% CH3OH in CH2Cl2 recovered the product. It was re-dissolved in CH2Cl2, and ethanol (20 mL) was added. Dichloromethane was rotor-evaporated to leave a suspension of the product in ethanol. It was cooled to room temperature, filtered, and washed with hexane. White solid: 839 mg (2.67 mmol, 90%). Anal. Calc. for C19H14N4O (MW 314.34): C, 72.60; H, 4.49; N, 17.82. Found: C, 72.66; H, 4.54; N, 17.54%. 1H NMR (400 MHz, [D6]dmso): delta = 8.66-8.62 (m, 1H), 8.03-7.94 (m, 2H), 7.55-7.51 (m, 1H), 7.50-7.44 (m, 4H), 7.43-7.38 (m, 4H), 7.35-7.29 (m, 2H) ppm. 13C NMR (100 MHz, CD2Cl2): delta = 163.34, 159.67, 150.20, 144.03, 142.58, 137.16, 129.79, 126.69, 125.64, 125.24, 122.19 ppm. ESI+ TOF MS: m/z 314 (M+, 70%).
  • 5
  • [ 5985-24-0 ]
  • [ 83-01-2 ]
  • dimethyl 4-((diphenylcarbamoyl)oxy)isophthalate [ No CAS ]
  • 6
  • [ 83-01-2 ]
  • [ 3056-33-5 ]
  • C20H18N6O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; N-ethyl-N,N-diisopropylamine; at 20℃; Take Compound a (3 g) in 60 ml of anhydrous pyridine was added 4.5 mL diisopropylethyl amineand 3.5 g of Ph2NCOCl 3.5 g, stirred at room temperature, TLC (MeOH / DCM = l: 10 ) track, until completion of thereaction was quenched with water and stirred for 10 min, spindry,add ethanol, water filtration to give a solid mixed solutionwas stirred for 2 h at 90 C reflux, washed several times with ethanol to give compound b.
  • 7
  • [ 83-01-2 ]
  • [ 3056-33-5 ]
  • C35H31FN6O8 [ No CAS ]
  • 8
  • [ 65826-95-1 ]
  • [ 83-01-2 ]
  • 5-methyl-N,N-diphenyl-2,3-dihydro-1H-indole-1-carboxamide [ No CAS ]
  • 9
  • [ 2343-22-8 ]
  • [ 83-01-2 ]
  • 5-fluoro-N,N-diphenylindoline-1-carboxamide [ No CAS ]
 

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