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Chemical Structure| 86-79-3 Chemical Structure| 86-79-3
Chemical Structure| 86-79-3
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Product Details of [ 86-79-3 ]

CAS No. :86-79-3
Formula : C12H9NO
M.W : 183.21
SMILES Code : OC1=CC(NC2=C3C=CC=C2)=C3C=C1
MDL No. :MFCD00004962
InChI Key :GWPGDZPXOZATKL-UHFFFAOYSA-N
Pubchem ID :93551

Safety of [ 86-79-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Calculated chemistry of [ 86-79-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 13
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 2.0
Molar Refractivity 57.83
TPSA ?

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

36.02 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.51
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

3.03
Log Po/w (WLOGP)?

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

3.03
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.

2.17
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

3.09
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.57

Water Solubility

Log S (ESOL):?

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

-3.57
Solubility 0.0491 mg/ml ; 0.000268 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.

-3.45
Solubility 0.0647 mg/ml ; 0.000353 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

-4.38
Solubility 0.00757 mg/ml ; 0.0000413 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

Yes
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

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

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.27 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)

1.3

Application In Synthesis of [ 86-79-3 ]

* 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 [ 86-79-3 ]

[ 86-79-3 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 86-79-3 ]
  • [ 77-78-1 ]
  • [ 6933-49-9 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; at 110℃; for 4.75h; Example 1 l-(2-Methoxy-9H-carbazol-9-yl)-3,3-dimethylbutan-2-oneStep A. 2-Methoxy-9H-carbazole2-?ydroxycarbazole (4.83 g) was suspended in 100 mL water. A solution of 1.11 g NaOH in 100 mL water and 3.83 g dimethyl sulfate were added. The mixture was heated in 110 C oil bath for 2.5 hours. After cooling the reaction mixture was filtered. The collected solid was washed with 100 mL each of water and 0.25 M NaOH solution to give a solid. The filtrate and wash was extracted with 4x50 mL ether. This ether solution was combined with 250 mL ethyl acetate solution of the solid collected and washed with 0.2 N NaOH, water, and saturated brine to give a mixture of product and the starting material. This crude product was treated with 6 mL 5 N NaOH and 4.0 mL dimethyl sulfate in 300 mL water at 110 C for 45 minutes. Then, 12.0 mL 5 N NaOH was added and the resulting mixture stirred for 30 minutes. An additional 2.0 mL dimethyl sulfate was added and the resulting mixture heated for another hour. Repeat this sequence with 4.0 mL 5 N NaOH and 2.0 mL dimethyl sulfate. After cooling the reaction mixture, it was filtered to collect the solid product. It was washed with water and dried to give the crude product. It was purified on SGC using 30-55% EtOAc in hexanes to give the title compound as a yellow solid. 1HNMR (CD3OD, 500 MHz) ? 7.92 (d, 7.8 Hz, IH), 7.89 (d, 8.5 Hz, IH), 7.37 (d, 8.0 Hz, IH), 7.25-7.28 (m, IH), 7.08-7.11 (m, IH), 6.96 (d, 2.3 Hz, IH), 6.77 (dd, 2.3 & 8.7 Hz, IH), 3.87 (s, 3H). LC-MS: 3.31 min. (m/Z = 198.1).
  • 2
  • [ 86-79-3 ]
  • [ 3386-35-4 ]
  • [ 137280-05-8 ]
  • BSc4029 [ No CAS ]
  • 3
  • [ 86-79-3 ]
  • [ 616-38-6 ]
  • [ 6933-49-9 ]
  • 4
  • [ 86-79-3 ]
  • [ 77-78-1 ]
  • [ 6933-49-9 ]
  • [ 51846-67-4 ]
  • [ 39027-93-5 ]
  • 5
  • [ 86-79-3 ]
  • MeX [ No CAS ]
  • [ 6933-49-9 ]
  • 6
  • [ 86-79-3 ]
  • [ 74-88-4 ]
  • [ 6933-49-9 ]
YieldReaction ConditionsOperation in experiment
49% With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; Synthesis of 2-methoxy-9H-carbazole: MeI (1.25 mL, 20 mmol, 1.0 eq) was added to a mixture of 9H-carbazol-2-ol (3.66 g, 20 mmol, 1.0 eq) and K2CO3 (2.76 g, 20 mmol, 1.0 eq) in DMF (40 mL). The mixture was stirred at room temperature for 23 hours, then quenched by water. The precipitate was filtered off and washed with ethyl acetate, and the collected solid was dried in air to afford the desired product as a white solid 1.94 g in 49% yield. 1H NMR (CDCl3, 500 MHz): delta 3.91 (s, 3H), 6.86 (dd, J=8.0, 2.5 Hz, 1H), 6.92 (d, J=2.0 Hz, 1H), 7.21 (t, J=8.0 Hz, 1H), 7.34 (t, J=8.0 Hz, 1H), 7.35 (d, J=7.5 Hz, 1H), 7.93-7.98 (m, 3H).
 

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