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
• Article Data: 18

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

General Description

3-Piperidin-4-yl-1H-indole, also known as PD168077, is a chemical compound that belongs to the indole class of organic compounds. It is a potent and selective agonist for the serotonin receptor 5-HT1E, with a Ki value of 1.6 nM. This receptor is known to be involved in the regulation of neurotransmitter release and may play a role in modulating mood and behavior. Due to its high affinity for the 5-HT1E receptor, PD168077 has been studied as a potential therapeutic agent for the treatment of various neurological and psychiatric disorders, such as depression, anxiety, and schizophrenia. Additionally, it has been used as a pharmacological tool in research to better understand the role of the 5-HT1E receptor in the brain and its potential as a target for drug development.

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 
• 41979-39-9 4-piperidone hydrochloride 
• 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 

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.

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.

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.