17403-09-7

Basic information

• Product Name: 3-Piperidin-4-yl-1H-indole
• Synonyms: 3-PIPERIDIN-4-YL-1H-INDOLE;3-(PIPERID-4-YL)INDOLE;4-(3-INDO)PIPERIDINE;3-(4-PIPERIDINO)INDOLE;3-(4'-PIPERIDINYL)-1H-INDOLE;3-(4-piperidyl)-1H-indole;3-(piperidinyl)Indole;3-(4'-Piperdinyl)-1H-Indole
• CAS NO: 17403-09-7
• Molecular Formula: C₁₃H₁₆N₂
• Molecular Weight: 200.28
• EINECS: 241-425-3
• Product Categories: pharmacetical
• Mol File: 17403-09-7.mol

Chemical Properties

• Melting Point: 222-224°C
• Boiling Point: 386.5 °C at 760 mmHg
• Flash Point: 187.5 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 3.03E-06mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 17.06±0.30(Predicted)
• CAS DataBase Reference: 3-Piperidin-4-yl-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Piperidin-4-yl-1H-indole(17403-09-7)
• EPA Substance Registry System: 3-Piperidin-4-yl-1H-indole(17403-09-7)

Safety Data

• Hazard Codes: Xi,C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: 3259
• Hazardous Substances Data: 17403-09-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Piperidin-4-yl-1H-indole is used as a potential therapeutic agent for the treatment of various neurological and psychiatric disorders, such as depression, anxiety, and schizophrenia. Its high affinity for the 5-HT1E receptor makes it a promising candidate for developing new treatments targeting this receptor.
Used in Research Applications:
3-Piperidin-4-yl-1H-indole is used as a pharmacological tool in research to better understand the role of the 5-HT1E receptor in the brain. It helps scientists explore the receptor's potential as a target for drug development and gain insights into the underlying mechanisms of mood and behavior regulation.

InChI:InChI=1/C13H16N2/c1-2-4-13-11(3-1)12(9-15-13)10-5-7-14-8-6-10/h1-4,9-10,14-15H,5-8H2/p+1

Upstream product

• 65347-55-9 3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole 
• 120-72-9 indole 
• 3612-20-2 1-phenylmethyl-4-piperidone 
• 179234-89-0 3-(1-benzylpiperidin-4-yl)-1H-indole 
• 41661-47-6 piperidin-4-one 
• 17403-05-3 3-[1,2,3,6-tetrahydro-1-(phenylmethyl)-4-pyridinyl]-1H-indole 
• 155302-28-6 tert.butyl 4-(1H-indol-3-yl)-piperidine-1-carboxylate 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 155302-27-5 3-[N-(t-butyloxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole 
• 41979-39-9 4-piperidone hydrochloride 

Downstream Products

• 57311-64-5 N-(2-(4-(1H-indol-3-yl)piperidin-1-yl)ethyl)phthalimide 

Relevant articles and documents

Synthesis of new bridged tetrahydro-β-carbolines and spiro-fused quinuclidines

Two series of chemically related, conformationally restricted ring systems were synthesized. Bridged tetrahydro-β-carbolines, designed as selective 5-HT receptor ligands, were formed via Pictet-Spengler condensation of cyclic tryptamine precursors. Oxidation of the indole 2-position of the precursors followed by condensation with aldehydes produced spiro-cyclic quinuclidines, containing important muscarine receptor pharmacophores.

Synthesis and biological evaluation of new multi-target 3-(1H-indol-3-yl)pyrrolidine-2,5-dione derivatives with potential antidepressant effect

A series of novel 3-(1H-indol-3-yl)pyrrolidine-2,5-dione derivatives were synthesised and evaluated for their 5-HT1A/D2/5-HT2A/5-HT6/5-HT7 receptor affinity and serotonin reuptake inhibition. Most of the evaluated compounds displayed high affinities for 5-HT1A receptors (e.g., 4c Ki = 2.3 nM, 4l Ki = 3.2 nM). The antidepressant activity of the selected compounds was screened in vivo using the forced swim test (FST). The results indicate that compound MW005 (agonist of the pre- and postsynaptic 5-HT1A receptor) exhibited promising affinities for the 5-HT1A/SERT/D2/5-HT6/5-HT7 receptors and showed an antidepressant-like activity in the FST model.

Substituted heterocyclic compounds and application of same to medicines

The invention relates to substituted heterocyclic compounds and application of the same to medicines and specifically provides the novel substituted heterocyclic compounds or stereoisomers, tautomers, nitrogen oxides, hydrates, solvates, metabolites, pharmaceutically acceptable salts or prodrugs thereof, and preparation methods thereof. The invention also relates to pharmaceutical compositions containing the compounds and application of the compounds or pharmaceutical compositions to treatment of diseases related to 5-HT6 receptors, especially Alzheimer's disease.

Substituted heterocyclic compounds and its application on the medicament (by machine translation)

The invention relates to substituted heterocyclic compounds and its application on the medicament, in particular to a novel class of substituted heterocyclic compounds or its isomer, tautomer, nitrogen oxide, hydrate, solvate, metabolite, pharmaceutically acceptable salt or prodrug, and their method of preparation. The invention also relates to the compounds of the invention pharmaceutical composition, and said compound or pharmaceutical compositions for the treatment5-HT6receptor-related diseases, in particular Alzheimer's disease in the use thereof. (by machine translation)

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.

Exploring the 3-piperidin-4-yl-1H-indole scaffold as a novel antimalarial chemotype

A series of 3-piperidin-4-yl-1H-indoles with building block diversity was synthesized based on a hit derived from an HTS whole-cell screen against Plasmodium falciparum. Thirty-eight compounds were obtained following a three-step synthetic approach and evaluated for anti-parasitic activity. The SAR shows that 3-piperidin-4-yl-1H-indole is intolerant to most N-piperidinyl modifications. Nevertheless, we were able to identify a new compound (10d) with lead-like properties (MW = 305; cLogP = 2.42), showing antimalarial activity against drug-resistant and sensitive strains (EC50 values ～ 3 μM), selectivity for malaria parasite and no cross-resistance with chloroquine, thus representing a potential new chemotype for further optimization towards novel and affordable antimalarial drugs.

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.

DIPHENYLBUTYPIPERIDINE AUTOPHAGY INDUCERS

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

Polystyrene sulfonyl chloride: A highly orthogonal linker resin for the synthesis of nitrogen-containing heterocycles

One linker, broad application: A simple sulfonamide linker for primary and secondary amines was used for the construction of small libraries of privileged indole and quinolone structures on a solid phase. After the synthesis, the products can be liberated ion a traceless manner under electron transfer conditions or according to a "safety catch" principle.

Novel 4-aryl-pyrido[1,2-c]pyrimidines with dual SSRI and 5-HT1A activity, Part 1

A series of new derivatives of 4-aryl-pyrido[1,2-c]pyrimidine containing the 3-(4-piperidyl)-1H-indole residue or its 5-methoxy derivative were synthesized. They were characterized (i) in vitro by binding to 5-HT1A receptors and 5-HT transporter proteins in rat brain cortex membranes and (ii) in vivo in the mouse by induced hypothermia and forced swimming models for antagonist/agonist activity against the 5-HT1A autoreceptors and postsynaptic 5-HT1A receptors, respectively. Structure activity relationship evaluation indicated that the presence of the 3-(4-piperidyl)-1H-indole residue and ortho- or para-substituents with -F or -CH3 groups in the aryl ring as well as an unsubstituted aryl in the 4-aryl-pyrido[1,2-c]pyrimidine moiety promoted low Ki values for both receptors. In contrast, the presence of a 5-methoxy-3-(4-piperidyl)-1H-indole residue as well as -Cl or -OCH3 substituents at the para position markedly reduced the receptor affinity.