65826-95-1|5-Methylindoline| Ambeed

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Quality Control of [ 65826-95-1 ] Purity: 97% SDS Specification

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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
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

Computational 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 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.88
Log P_o/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 P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.39
Log P_o/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 P_o/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 P_o/w? Consensus Log P_o/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 of [ 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 1~36

1
[ 394-47-8 ]
[ 65826-95-1 ]
[ 96014-87-8 ]

Yield	Reaction Conditions	Operation 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.

References: [1]Patent: US4663453,1987,A .
[2]Journal of Heterocyclic Chemistry,1987,vol. 24,p. 1599 - 1604.

2
[ 614-96-0 ]
[ 65826-95-1 ]

References: [1]Organic Letters,2011,vol. 13,p. 5124 - 5127.
[2]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6073 - 6084.
[3]Journal of the American Chemical Society,2015,vol. 137,p. 11718 - 11724.
[4]Synthetic Communications,2010,vol. 40,p. 1837 - 1846.
[5]Journal of Medicinal Chemistry,1998,vol. 41,p. 1598 - 1612.
[6]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 3105 - 3109.
[7]Tetrahedron Letters,2005,vol. 46,p. 1423 - 1425.
[8]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3287 - 3291.
[9]Journal of Medicinal Chemistry,2011,vol. 54,p. 166 - 178.
[10]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 373 - 377.
[11]Organic and Biomolecular Chemistry,2013,vol. 11,p. 1209 - 1215.
[12]RSC Advances,2015,vol. 5,p. 23727 - 23736.
[13]Advanced Synthesis and Catalysis,2015,vol. 357,p. 3529 - 3537.
[14]Journal of Organic Chemistry,2016,vol. 81,p. 396 - 403.
[15]Journal of Organic Chemistry,2018,vol. 83,p. 2425 - 2437.
[16]Chemical Communications,2018,vol. 54,p. 2494 - 2497.
[17]Chemistry - A European Journal,2019,vol. 25,p. 8245 - 8248.

3
[ 65826-95-1 ]
[ 15268-31-2 ]
5-methyl-1-(3-pyridylcarbamoyl)indoline [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 1598 - 1612.
[2]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 2767 - 2773.

4
[ 65826-95-1 ]
[ 100-47-0 ]
[ 179024-62-5 ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4850 - 4867.
[2]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 35 - 38.

5
[ 65826-95-1 ]
[ 79-04-9 ]
2-chloro-1-(5-methyl-2,3-dihydro-indol-1-yl)-ethanone [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 3105 - 3109.
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2613 - 2616.

6
[ 500227-35-0 ]
[ 65826-95-1 ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 5139 - 5146.
[2]Organic Letters,2003,vol. 5,p. 189 - 191.

7
[ 65826-95-1 ]
[ 614-96-0 ]

Yield	Reaction Conditions	Operation 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.

References: [1]Chemical Science,2019,vol. 10,p. 4883 - 4889.
[2]Heterocycles,2007,vol. 74,p. 629 - 635.
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 3080 - 3084.
Angew. Chem.,2017,vol. 129,p. 3126 - 3130,5.
[4]ACS Catalysis,2018,vol. 8,p. 11679 - 11687.
[5]Advanced Synthesis and Catalysis,2014,vol. 356,p. 189 - 198.
[6]Tetrahedron Letters,2018,vol. 59,p. 3958 - 3960.
[7]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3958 - 3964.
[8]Organic and biomolecular chemistry,2020,vol. 18,p. 2103 - 2112.
[9]Tetrahedron Letters,2003,vol. 44,p. 6207 - 6210.

8
[ 22980-09-2 ]
[ 65826-95-1 ]
[ 861709-97-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 6073 - 6084.
[2]Tetrahedron Letters,2005,vol. 46,p. 1423 - 1425.

9
[ 65826-95-1 ]
[ 536-74-3 ]
4,8-dimethyl-4,6-diphenyl-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 5782 - 5783.

10
[ 2576-47-8 ]
[ 65826-95-1 ]
[ 552866-97-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3287 - 3291.

11
[ 65826-95-1 ]
1-(2-bromo-phenyl)-3-[2-(5-methyl-2,3-dihydro-indol-1-yl)-ethyl]-urea [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3287 - 3291.

12
[ 65826-95-1 ]
1-[2-(1H-indol-3-yl)ethyl]-5-methyl-1H-indole [ No CAS ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 1423 - 1425.

13
[ 65826-95-1 ]
[ 849226-75-1 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 1423 - 1425.

14
[ 65826-95-1 ]
2-[4-(4-chloro-benzyl)-piperazin-1-yl]-1-(5-methyl-2,3-dihydro-indol-1-yl)-ethanone [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 3105 - 3109.

15
[ 65826-95-1 ]
[ 179024-52-3 ]