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Chemical Structure| 65826-95-1 Chemical Structure| 65826-95-1
Chemical Structure| 65826-95-1

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5-Methylindoline

CAS No.: 65826-95-1

4.5 *For Research Use Only !

Cat. No.: A239758 Purity: 97%

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Product Details of [ 65826-95-1 ]

CAS No. :65826-95-1
Formula : C9H11N
M.W : 133.19
SMILES Code : CC1=CC2=C(NCC2)C=C1
MDL No. :MFCD03093636
Boiling Point : No data available
InChI Key :JFUAVVHABJWSFX-UHFFFAOYSA-N
Pubchem ID :14023679

Safety of [ 65826-95-1 ]

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

Calculated chemistry of [ 65826-95-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.33
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 1.0
Molar Refractivity 46.5
TPSA ?

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

12.03 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.88
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

2.3
Log Po/w (WLOGP)?

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

1.39
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.

2.06
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

2.7
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.07

Water Solubility

Log S (ESOL):?

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

-2.56
Solubility 0.368 mg/ml ; 0.00276 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.

-2.19
Solubility 0.859 mg/ml ; 0.00645 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

-3.35
Solubility 0.0591 mg/ml ; 0.000444 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.

-5.48 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

2.0
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)

1.19

Application In Synthesis [ 65826-95-1 ]

* 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 [ 65826-95-1 ]

[ 65826-95-1 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 394-47-8 ]
  • [ 65826-95-1 ]
  • [ 96014-87-8 ]
YieldReaction ConditionsOperation in experiment
73% In ethanol; n-heptane; dimethyl sulfoxide; EXAMPLE 54 2-(5-Methylindolin-1-yl)benzonitrile A slurry of <strong>[65826-95-1]5-methylindoline</strong> (31 g, 0.23 mole), sodium hydride (11.3 g, 60% in oil) and dimethylsulfoxide (120 ml) was stirred at room temperature for 1 hour. A solution of o-fluorobenzonitrile (31 gm, 0.25 mole) in dimethylsulfoxide (25 ml) was added dropwise at a temperature below 20 C. Upon completion of the addition, the mixture was stirred for 2 hours at room temperture. The reaction mixture was partitioned between methylene chloride (700 ml) and ice-water (700 ml). The dichloromethane solutions were separated. The aqueous phase was extracted with dichloromethane (2 times, 600 ml). The combined dichloromethane solutions were washed with 2N hydrochloric acid (2 times, 500 ml), water (500 ml), brine (2 times, 400 ml), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was dissolved in ethanol (300 ml) and heptane (100 ml), and chilled in a freezer. The precipitate was collected. The mother liquor was concentrated and purified by flash chromatography on a silica gel column (400 g, 230-400 mesh) eluted with hexane:dichloromethane (3:1, 3 l); hexane:dichloromethane (1:1, 2 l) and dichloromethane (2 l). The fractions containing product were pooled and concentrated to yield 33 g (73% overall yield). The analytical sample was prepared by high-pressure liquid chromatography (Water Associates Prep 500, 10 g, 2 chamber, elution with hexane:dichloromethane, 9:1, 12 l) followed by crystallization from ethanol, mp 59-60 C. ANALYSIS: Calculated for C16 H14 N2: 82.02%C 6.02%H 11.96%N. Found: 82.47%C 6.08%H 12.10%N.
  • 3
  • [ 65826-95-1 ]
  • [ 15268-31-2 ]
  • 5-methyl-1-(3-pyridylcarbamoyl)indoline [ No CAS ]
  • 5
  • [ 65826-95-1 ]
  • [ 79-04-9 ]
  • 2-chloro-1-(5-methyl-2,3-dihydro-indol-1-yl)-ethanone [ No CAS ]
  • 7
  • [ 65826-95-1 ]
  • [ 614-96-0 ]
YieldReaction ConditionsOperation in experiment
89% With trimethylamine-N-oxide; In toluene; at 100℃; for 20h;Inert atmosphere; Schlenk technique; General procedure: In a 2-neck RBF, 1 (20 mg, 0.0005 mmol) and TMNO (45 mg, 0.6 mmol) were suspended in toluene (4 mL) and to this solution indoline (60 mg, 0.5 mmol) was added. The reaction mixture was then heated to 100 oC for 20 h and it was filtered and solvent evaporated. The crude product obtained was purified by column chromatography using hexane/ethylacetate (7:1) as eluent to give pure indole (47 mg, 79%). A similar procedure was used for the other indolines and N-heterocycles.
  • 9
  • [ 65826-95-1 ]
  • [ 536-74-3 ]
  • 4,8-dimethyl-4,6-diphenyl-1,2-dihydro-4<i>H</i>-pyrrolo[3,2,1-<i>ij</i>]quinoline [ No CAS ]
  • 10
  • [ 2576-47-8 ]
  • [ 65826-95-1 ]
  • [ 552866-97-4 ]
  • 11
  • [ 65826-95-1 ]
  • 1-(2-bromo-phenyl)-3-[2-(5-methyl-2,3-dihydro-indol-1-yl)-ethyl]-urea [ No CAS ]
  • 12
  • [ 65826-95-1 ]
  • 1-[2-(1H-indol-3-yl)ethyl]-5-methyl-1H-indole [ No CAS ]
  • 13
  • [ 65826-95-1 ]
  • [ 849226-75-1 ]
  • 14
  • [ 65826-95-1 ]
  • 2-[4-(4-chloro-benzyl)-piperazin-1-yl]-1-(5-methyl-2,3-dihydro-indol-1-yl)-ethanone [ No CAS ]
  • 15
  • [ 65826-95-1 ]
  • [ 179024-52-3 ]
  • 16
  • [ 65826-95-1 ]
  • [ 179024-54-5 ]
  • 17
  • [ 65826-95-1 ]
  • [ 179024-53-4 ]
  • 18
  • [ 65826-95-1 ]
  • [ 179024-48-7 ]
  • 19
  • [ 65826-95-1 ]
  • 2-methoxy-<i>N</i>-(9-methyl-4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-<i>hi</i>]indol-3-yl)-benzamide [ No CAS ]
  • 20
  • [ 65826-95-1 ]
  • 4-chloro-<i>N</i>-(9-methyl-4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-<i>hi</i>]indol-3-yl)-benzamide [ No CAS ]
  • 21
  • [ 65826-95-1 ]
  • isoquinoline-3-carboxylic acid (9-methyl-4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-<i>hi</i>]indol-3-yl)-amide [ No CAS ]
  • 22
  • [ 65826-95-1 ]
  • 2,4-dichloro-<i>N</i>-(9-methyl-4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-<i>hi</i>]indol-3-yl)-benzamide [ No CAS ]
  • 23
  • [ 65826-95-1 ]
  • 3,5-dichloro-<i>N</i>-(9-methyl-4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-<i>hi</i>]indol-3-yl)-benzamide [ No CAS ]
  • 24
  • [ 65826-95-1 ]
  • 2,4-dimethoxy-<i>N</i>-(9-methyl-4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-<i>hi</i>]indol-3-yl)-benzamide [ No CAS ]
  • 25
  • [ 65826-95-1 ]
  • 7-methyl-pyrazolo[5,1-<i>c</i>][1,2,4]triazine-3-carboxylic acid (9-methyl-4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]diazepino[6,7,1-<i>hi</i>]indol-3-yl)-amide [ No CAS ]
 

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