3468-18-6|(1H-Indol-4-yl)methanamine| Ambeed

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Quality Control of [ 3468-18-6 ] Purity: 95% SDS Specification

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NMR

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HPLC

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Product Citations

Inhibition of ATP Production in Pancreatic Cancer Cells by a Library of N‐(1H‐Indol‐4‐ylmethyl) benzenesulfonamide and N‐(1H‐Indol‐5‐ylmethyl) benzenesulfonamide Analogs

Witt, Ryan C ; Dunn, Caroline E ; Zanders, Levi A ; Edema, Adeleye A ; Waheed, Sakariyau A ; Derewonko, Carina A , et al.

DOI: 10.1002/cmdc.202500136 PubMed ID: 40295191 ChemMedChem,2025,e202500136.

Abstract: A library of 50 indolyl sulfonamides and 9 amide analogs based upon the 4-indolyl and 5-indolyl frameworks has been synthesized to target the metabolic processes of pancreatic cancer. Thirteen of the 50 compounds were identified as cytotoxic at 50 μM using a traditional (48-hour compound exposure) assay against 7 pancreatic cancer cell lines and 1 non-cancerous cell line. The potential role of the compounds as metabolic inhibitors of ATP production was then evaluated using a rapid screening (1-2 hour compound exposure) assay developed within our laboratories. The rapid assay identified 10 compounds as strong or moderate hits at 3 μM against the panel of pancreatic and non-cancerous cell lines. The IC₅₀ values of the active compounds were determined using the rapid assay in the absence of glucose and four of the compounds displayed an IC₅₀ value <1 μM against one or more pancreatic cancer cell lines. Comparison of IC₅₀ values of the active compounds in the presence of glucose implicates the potential role of the compounds as oxidative phosphorylation (OXPHOS) inhibitors of ATP production. Lastly, a series of amide analogs were synthesized and screened for activity to determine the structural importance of the sulfonamide functionality.

Keywords: Indole ; oxidative phosphorylation inhibitor ; OXPHOS inhibitor ; pancreatic cancer ; chemotherapy resistance

Purchased from AmBeed: 81881-74-5 ; 3468-18-6

Product Details of [ 3468-18-6 ]

CAS No. :	3468-18-6
Formula :	C₉H₁₀N₂
M.W :	146.19
SMILES Code :	NCC1=CC=CC2=C1C=CN2
Synonyms :	NSC 131886
MDL No. :	MFCD04973297
InChI Key :	FFBWKPKOXRMLNP-UHFFFAOYSA-N
Pubchem ID :	280302

Safety of [ 3468-18-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 3468-18-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.11
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	2.0
Molar Refractivity	45.97
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	41.81 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.25
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	0.91
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.47
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.	0.96
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	2.14
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.35

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.86
Solubility	2.02 mg/ml ; 0.0138 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.37
Solubility	6.19 mg/ml ; 0.0423 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-3.31
Solubility	0.0721 mg/ml ; 0.000493 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	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	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.55 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)	1.17

Application In Synthesis of [ 3468-18-6 ]

* 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 [ 3468-18-6 ]

[ 3468-18-6 ] Synthesis Path-Downstream 1~35

1
[ 98-03-3 ]
[ 3468-18-6 ]
[ 53462-74-1 ]

References: [1]Journal of Medicinal Chemistry,1974,vol. 17,p. 1140 - 1145.

3
[ 3468-18-6 ]
[ 647828-37-3 ]
[6-(4-ethoxy-phenyl)-4,5,7-trimethyl-6H-pyrrolo[3,4-d]pyridazin-1-yl]-(1H-indol-4-ylmethyl)-amine [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 746 - 749.

4
[ 1074-86-8 ]
[ 3468-18-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium borohydrid; methylamine; In methanol; water;	Step C: To a solution of aldehyde product from Step B (2.0 g, 14 mmol) in methanol (100 mL), 40% methylamine in water (2.27 mL, 27.6 mmol) was added at room temperature over a period of 10 min. The mixture was stirred at room temperature under nitrogen overnight and then was cooled down to 0 C. Sodium borohydride (1.05 g, 27.6 mmol) was added. The reaction mixture was slowly warmed to room temperature for 2 h. Most of methanol was removed in vacuo, and the residue was diluted with water and extracted (3) with ether. The combined organic layers were extracted with 2 N HCl (100 mL). The HCl layer was made basic (pH~11) with 2 N NaOH and extracted (3) with methylene chloride. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to give crude 4-(aminomethyl)-indole as a white powder (1.95 g, 88%): 1H NMR (300 MHz, CDCl3) delta 8.29 (s, br, 1H), 7.31 (d, J=8.0 Hz, 1H), 7.22 (t, J=2.7 Hz, 1H), 7.16 (t, J=8.0, 7.3 Hz, 1H), 7.08 (d, J=7.3 Hz, 1H), 6.64 (t, J=2.0 Hz, 1H), 4.06 (s, 2H), 2.51 (s, 3H); CI MS m/z=160 [C10H12N2+H]+.

References: [1]Patent: US2002/91134,2002,A1 .

5
[ 16136-52-0 ]
[ 144-55-8 ]
[ 3468-18-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium hydroxide; In tetrahydrofuran;	Example 10 Preparation of 1H-indole-4-methanamine Lithium aluminum hydride (3.80 g, 100.0 mmol) was added in 0.5 g portions over 30 min to a solution of 1H-indole-4-carbonitrile (prepared according to Clark, Robin D.; Repke, David B. J. Heterocycl. Chem. 1985, 22, 121-5; 7.50 g, 52.8 mmol) in tetrahydrofuran (250 mL). The mixture was heated at reflux for 30 min. A solution of 1 M sodium hydroxide was added to quench excess lithium aluminum hydride. The mixture was filtered and the filter cake was washed with water. The filtrate was first made acidic with 1 N HCl and then made basic again by the addition of saturated aqueous NaHCO3. The water layer was then extracted with nBuOH. Evaporation of nBuOH, and drying under vacuum gave 1H-indole-4-methanamine (6.24 g, 80%) as a beige solid.

References: [1]Patent: US6331640,2001,B1 .

6
[ 16136-52-0 ]
[ 3468-18-6 ]

Yield	Reaction Conditions	Operation in experiment
94%		Preparation of C-(1H-indol-4-yl)-methylamine To a solution of 4-cyanoindole (7.5 g, 53 mmol) in THF (100 ml) was added at rt a 1.0M solution of lithium aluminum hydride in THF (100 ml, 100 mmol). The mixture was refluxed for 30 min then cooled to rt. The reaction mixture was quenched with 1N NaOH and filtered. The filtrate was acidified with 1N HCl and stirred at rt for 10 min. The pH was adjusted to ~8 by adding sat NaHCO3 and extracted with n-butanol. The layers were separated and the organic layer was concentrated to dryness. The residue was triturated with methanol. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure to afford the desired product as a solid that was further dried under high vacuum at 50 C. (7.27 g, 94% yield).
82%	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; under 2068.65 - 2172.08 Torr;Inert atmosphere;	Method B. 4-cynoindole (1.0 mmol) was dissolved in MeOH in a hydrogenator reaction flask, 10% Pd/C (10 mg) was added and hydrogenator was shook at 40-42 psi overnight. Reaction mixture was carefully taken out from hydrogenator, filtered through celite and purified by column chromatography (EtOAc: MeOH; 9.5: 0.5) with few drops of aqueous ammonia.

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 2646 - 2650.
[2]Patent: US2012/238569,2012,A1 .Location in patent: Page/Page column 29.
[3]Chemical Science,2018,vol. 9,p. 8553 - 8560.
[4]European Journal of Medicinal Chemistry,2017,vol. 134,p. 13 - 23.
[5]Catalysis science and technology,2014,vol. 4,p. 629 - 632.

7
[ 22901-09-3 ]
[ 3468-18-6 ]
[ 1217181-05-9 ]

References: [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 2646 - 2650.

8
[ 1158519-17-5 ]
[ 3468-18-6 ]
[ 1373945-72-2 ]

References: [1]Organic Letters,2012,vol. 14,p. 2610 - 2613.

9
[ 1158519-18-6 ]
[ 3468-18-6 ]
[ 1373945-74-4 ]

References: [1]Organic Letters,2012,vol. 14,p. 2610 - 2613.

10
[ 1373945-13-1 ]
[ 3468-18-6 ]
[ 1373945-62-0 ]

References: [1]Organic Letters,2012,vol. 14,p. 2610 - 2613.

11
[ 1373945-16-4 ]
[ 3468-18-6 ]
[ 1373945-64-2 ]

References: [1]Organic Letters,2012,vol. 14,p. 2610 - 2613.

12
[ 1373945-18-6 ]
[ 3468-18-6 ]
C₂₂H₁₆F₂N₄O [ No CAS ]
[ 1373945-66-4 ]

References: [1]Organic Letters,2012,vol. 14,p. 2610 - 2613.

13
[ 1373945-22-2 ]
[ 3468-18-6 ]
[ 1373945-68-6 ]

References: [1]Organic Letters,2012,vol. 14,p. 2610 - 2613.

14
[ 1373946-77-0 ]
[ 3468-18-6 ]
[ 1373945-70-0 ]

References: [1]Organic Letters,2012,vol. 14,p. 2610 - 2613.

15
[ 1373945-36-8 ]
[ 3468-18-6 ]
[ 1373945-76-6 ]

References: [1]Organic Letters,2012,vol. 14,p. 2610 - 2613.

16
[ 3468-18-6 ]
[ 1400661-83-7 ]