65347-55-9

Basic information

• Product Name: 3-(1,2,3,6-TETRAHYDROPYRIDIN-4-YL)-1H-INDOLE
• Synonyms: 3-(1,2,3,6-TETRAHYDRO-4-PYRINYL)-1H-INDOLE;3-(1,2,3,6-TETRAHYDROPYRIDIN-4-YL)-1H-INDOL-5-OL;3-(1,2,3,6-TETRAHYDROPYRIDIN-4-YL)-1H-INDOLE;4-(1H-Indol-3-yl)-1,2,3,6-tetrahydropyridine;1H-Indole, 3-(1,2,3,6-tetrahydro-4-pyridinyl)-;3-(1,2,3,6-Tetrahydro-4-pyridyl)indole
• CAS NO: 65347-55-9
• Molecular Formula: C₁₃H₁₄N₂
• Molecular Weight: 198.26
• Mol File: 65347-55-9.mol

Chemical Properties

• Melting Point: 177-182°C
• Boiling Point: 400.4 °C at 760 mmHg
• Flash Point: 195.9 °C
• Appearance: /Solid
• Density: 1.163 g/cm³
• Vapor Pressure: 2.42E-09mmHg at 25°C
• Refractive Index: 1.691
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-(1,2,3,6-TETRAHYDROPYRIDIN-4-YL)-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1,2,3,6-TETRAHYDROPYRIDIN-4-YL)-1H-INDOLE(65347-55-9)
• EPA Substance Registry System: 3-(1,2,3,6-TETRAHYDROPYRIDIN-4-YL)-1H-INDOLE(65347-55-9)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 65347-55-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(1,2,3,6-TETRAHYDROPYRIDIN-4-YL)-1H-INDOLE is used as a potential therapeutic agent for various applications due to its indole derivative nature and the pharmacological properties associated with such compounds. Its potential uses may include anti-inflammatory, anticancer, and antimicrobial applications, depending on the outcomes of further research into its specific biological activities and interactions with biological systems.
Used in Research and Development:
3-(1,2,3,6-TETRAHYDROPYRIDIN-4-YL)-1H-INDOLE serves as a valuable compound in scientific research and development, particularly in the fields of medicinal chemistry and drug discovery. Its unique structure and potential biological activities make it a candidate for exploration in the development of new drugs and therapies, as well as for understanding the mechanisms of action of indole derivatives in biological systems.

InChI:InChI=1/C13H14N2O/c16-10-1-2-13-11(7-10)12(8-15-13)9-3-5-14-6-4-9/h1-3,7-8,14-16H,4-6H2

Upstream product

• 41661-47-6 piperidin-4-one 
• 120-72-9 indole 
• 40064-34-4 4-piperidone monohydrochloride monohydrate 
• 1336-21-6 ammonium hydroxide 
• 40064-34-4 piperidine-4,4-diol hydrochloride 
• 41979-39-9 4-piperidone hydrochloride 

Downstream Products

• 60155-63-7 4-(1H-indol-3-yl)piperidinium chloride 
• 695211-85-9 4-(1H-indol-3-yl)-piperidine-1-carboxylic acid (4-dimethylamino-4-phenyl-cyclohexylmethyl)-amide 
• 72826-65-4 (propyl-1 tetrahydro-1,2,3,6 pyridinyl-4)-3 1H-indole (chlorohydrate) 
• 72808-69-6 3-(1-pentyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole hydrochloride 
• 460353-65-5 SSA-426 

Relevant articles and documents

Inhibitors of the serotonin transporter protein (SERT): The design and synthesis of biotinylated derivatives of 3-(1,2,3,6-tetrahydro-pyridin-4-yl)-1H- indoles. High-affinity serotonergic ligands for conjugation with quantum dots

There is a growing demand for compounds with specificity for the serotonin transporter protein (SERT) that can be conjugated to cadmium selenide/zinc sulfide core shell nanocrystals. This letter describes the design and synthesis of two different biotinylated SERT antagonists that can be attached to streptavidin-coated cadmium selenide/zinc sulfide core shell nanocrystals.

PHARMACEUTICAL COMPOUND

Provided is a tryptophan-2,3-dioxygenase (TDO) and/or indoleamine-2,3-dioxygenase (IDO) inhibitor compound for use in medicine, which compound comprises the following formula: wherein X2, X4, X10, and X11 may be the same or different and each is independently selected from C and N; X1, X3, X5, X6, X7, X8, and X9 may be the same or different and each is independently selected from C, N and O; each bond having a dotted line may independently be a double bond or a single bond, provided that valencies at each atom are maintained; the dotted lines joining X4 with the carbon atoms either side of X2 are single bonds, and are only present when X2 is absent, X3 is absent and X4 is C, and when these bonds are present the ring carbons on each side of X2 are not directly bonded to each other; each R1 may be present or absent and may be the same or different and is selected from H and a substituted or unsubstituted organic group, provided that the number of R1 groups present is such that the valency of X1 is maintained; each R12, R13, R13', R14, R15 and R15 may be present or absent and may be the same or different and each is independently selected from H and a substituted or unsubstituted organic group, provided that the number of such R groups present is such that the valency of the ring carbon atoms is maintained; R16 may be present or absent and is selected from H and a substituted or unsubstituted organic group, provided that the number of R16 groups present is such that the valency of X2 is maintained; each R17 may be present or absent and may be the same or different and is independently selected from H and a substituted or unsubstituted organic group, provided that the number of R17 groups present is such that the valency of X3 is maintained; each R2, R3, R4, and R5 may be present or absent and may be the same or different and is selected from H and a substituted or unsubstituted organic group, provided that the number of such R groups present is such that the valencies of X6, X7, X8, and X9 are maintained; each R7, R8 and R9 may be present or absent and may be the same or different and is selected from H and a substituted or unsubstituted organic group, provided that the number of such R groups present is such that the valencies of X10, X11, and X5 are maintained; and R6 is selected from H and a substituted or unsubstituted organic group, preferably H and a substituted or unsubstituted C1-C6 alkyl group; and wherein any R group may form a ring with any other R group on an adjacent and/or proximal atom.

Synthesis and biological evaluation of novel pyrrolidine-2,5-dione derivatives as potential antidepressant agents. Part 1

A series of 3-(1H-indol-3-yl)pyrrolidine-2,5-dione derivatives was synthesized and their biological activity was evaluated. The chemical structures of the newly prepared compounds were confirmed by 1H NMR, 13C NMR and ESI-HRMS spectra data. All tested compounds proved to be potent 5-HT1A receptor and serotonin transporter protein (SERT) ligands. Among them, compounds 15, 18, 19 and 30 showed significant affinity for 5-HT1A and SERT. Computer docking simulations carried out for compounds 15, 31 and 32 to models of 5-HT1A receptor and SERT confirm the results of biological tests. Due to high affinity for the 5-HT1A receptor and moderate affinity for SERT, compounds 31, 32, 35, and 37 were evaluated for their affinity for D2L, 5-HT6, 5-HT 7 and 5-HT2A receptors. In vivo tests, in turn, resulted in determining the functional activity of compounds 15, 18, 19 and 30 to the 5-HT1A receptor. The results of these tests indicate that all of the ligands possess properties characteristic of 5-HT1A receptor agonists.

Synthesis and SAR study of 4-arylpiperidines and 4-aryl-1,2,3,6- tetrahydropyridines as 5-HT2C agonists

A series of substituted 4-arylpiperidines and a smaller family of 4-aryl-1,2,3,6-tetrahydropyridines were synthesized and their biological activity at the 5-HT2C receptor studied to determine whether either series showed noteworthy agonist activity. Structure-activity relationships were developed from the performed receptor binding assays and functional studies, and the results of the analysis are presented herein.

DIPHENYLBUTYPIPERIDINE AUTOPHAGY INDUCERS

Autophagy inducing compounds, methods of their preparation and use, and kits containg said compounds are disclosed herein.

Tetrahydropyridin-4-yl indoles with a combination of affinity for dopamine-D2 receptors and serotonin reuptake sites

The present invention relates to a group of novel tetrahydropyridin-4-yl indoles with a dual mode of action: serotonin reuptake inhibition and affinity for dopamine-D2 receptors, to methods for the preparation of these compounds and to novel intermediates useful for the synthesis of said tetrahydropyridin-4-yl indoles. The invention also relates to the use of a compound disclosed herein for the manufacture of a medicament giving a beneficial effect. The invention relates to novel tetrahydropyridin-4-yl indoles of the formula. and tautomers, stereoisomers, prodrugs, N-oxides, pharmacologically acceptable salts, hydrates and solvates thereof, wherein: R1 is hydrogen, halogen, alkyl(C1-3) or alkoxy(C1-3), CN or CF3, R2 is hydrogen or alkyl(C1-3), R3 is hydrogen or alkyl(C1-3), Z is hydrogen or alkyl(C1-3), alkoxy(C1-3) or alkylthio(C1-3), A is hydrogen or alkyl(C1-3), or A and Z together form a saturated or (partly) unsaturated 5- or 6-membered ring which may be substituted with halogen, alkyl (C1-3) or phenyl, in which ring Z represents carbon, sulfur of nitrogen.

4-SUBSTITUTED 1-AMINOCYCLOHEXANE DERIVATIVES FOR UTILIZATION AS ORL1-RECEPTOR AND MU-OPIATE RECEPTOR LIGANDS

The invention relates to 4-substituted 1-aminocyclohexane derivatives of general formula (I), to a method for the production thereof, to medicaments containing said compounds and to the utilization of 4-substituted 1-aminocyclohexane derivatives for the production of medicaments.

Synthesis and structure-activity relationships of novel histamine H 1 antagonists: Indolylpiperidinyl benzoic acid derivatives

A series of indolylpiperidinyl derivatives were prepared and evaluated for their activity as histamine H1 antagonists. Structure-activity relationship studies were directed toward improving in vivo activity and pharmacokinetic profile of our first lead (1). Substitution of fluorine in position 6 on the indolyl ring led to higher in vivo activity in the inhibition of histamine-induced cutaneous vascular permeability assay but lower selectivity toward 5HT2 receptor. Extensive optimization was carried out within this series and a number of histamine H1 antagonists showing potency and long duration of action in vivo and low brain penetration or cardiotoxic potential were identified. Within this novel series, indolylpiperidines 15, 20, 48, 51 and 52 exhibited a long half-life in rat and have been selected for further preclinical evaluation.

INDOLYLPIPERIDINE DERIVATIVES AS ANTIHISTAMINIC AND ANTIALLERGIC AGENTS

The invention relates to indolyl piperidinyl derivatives of formula (I) wherein: A1 represents an alkylene, alkyleneoxy, alkylenethio, alkanoylene or hydroxyalkylene group; A2 represents an alkylene, alkyleneoxy, alkylenethio, alkanoylene or an alkyleneoxyalkylene group; W1 represents a phenylene, furanylene or pyridinylene group which is unsubstituted or substituted by one or more halogen atoms, alkoxy groups and/or alkyl groups; W2 represents a 3-10 membered monocyclic or bicyclic group containing from 1 to 3 heteroatoms said group being unsubstituted or substituted by one or more halogen atoms, alkyl groups, alkoxy groups and/or oxo groups; R1 represents a hydrogen or halogen atom or an alkyl, alkoxy or methylamino group; and R2 represents a carboxyl group; and pharmaceutically acceptable salts thereof; to processes for their preparation; to pharmaceutical compositions containing them; and to their medical use as antihistaminic and antiallergic agents.

NEW INDOLYLPIPERIDINE DERIVATIVES AS POTENT ANTIHISTAMINIC AND ANTIALLERGIC AGENTS

This invention is directed to new potent and selective antagonists of H1 histamine receptors having the general formula (I) to processes for their preparation; to pharmaceutical compositions comprising them; and to their use in therapy as antiallergic agents.