594827-31-3

Basic information

• Product Name: 1H-Indole, 1-[1-(2-pyridinylmethyl)-4-piperidinyl]-
• Synonyms: 1-[1-(Pyridin-2-ylmethyl)piperidin-4-yl]-1H-indole; 1H-indole, 1-[1-(2-pyridinylmethyl)-4-piperidinyl]-
• CAS NO: 594827-31-3
• Molecular Formula: C₁₉H₂₁N₃
• Molecular Weight: 291.3901
• Mol File: 594827-31-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 454.4°C at 760 mmHg
• Flash Point: 228.6°C
• Appearance: /
• Density: 1.16g/cm³
• Vapor Pressure: 1.91E-08mmHg at 25°C
• Refractive Index: 1.645
• CAS DataBase Reference: 1H-Indole, 1-[1-(2-pyridinylmethyl)-4-piperidinyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 1-[1-(2-pyridinylmethyl)-4-piperidinyl]-(594827-31-3)
• EPA Substance Registry System: 1H-Indole, 1-[1-(2-pyridinylmethyl)-4-piperidinyl]-(594827-31-3)

Safety Data

• Hazardous Substances Data: 594827-31-3(Hazardous Substances Data)

Usage

Chemical Class

Indole derivatives

Biological Activity

Anxiolytic and analgesic effects

Target Receptor

α2-adrenergic receptor

Therapeutic Use

Potential treatment for central nervous system disorders (e.g. anxiety, depression, pain)

Chemical Structure

Contains a piperidine and a pyridine ring, as well as an indole core

Importance

Represents an interesting compound for further research and development in neuropharmacology.

InChI:InChI=1/C19H21N3/c1-2-7-19-16(5-1)8-14-22(19)18-9-12-21(13-10-18)15-17-6-3-4-11-20-17/h1-8,11,14,18H,9-10,12-13,15H2

Upstream product

• 6959-47-3 2-chloromethylpyridine hydrochloride 
• 118511-81-2 1-(4-piperidinyl)-1H-indole 
• 150760-45-5 2-(2,2-dimethoxyethyl)-benzeneamine 
• 41661-56-7 1-(2-pyridinylmethyl)-piperidin-4-one 
• 616898-68-1 1-(1-(pyridin-2-ylmethyl)piperidin-4-yl)indoline 
• 496-15-1 1-indoline 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 158867-78-8 N,N-bis(2-ethoxycarbonylethyl)-N-(2-pyridilmethyl)amine 
• 32989-69-8 trans-2-nitro-β-pyrrolidinostyrene 
• 170365-11-4 1-(1-Benzyl-piperidin-4-yl)-1H-indole 
• 170364-89-3 4-(indol-1-yl)piperidine-1-carboxylic acid tert-butyl ester 
• 400828-91-3 tert-butyl 4-(indolin-1-yl) piperidine-1-carboxylate 
• 3731-51-9 2-(Aminomethyl)pyridine 
• 79844-33-0 2-(2-nitrophenyl)acetaldehyde dimethyl acetal 

Downstream Products

• 170364-57-5 enzastaurin 
• 1293289-28-7 3-(1-(phenylsulfonyl)-1H-indol-3-yl)-4-(1-(1-(pyridin-2-ylmethyl)piperidin-4-yl)-1H-indol-3-yl)furan-2,5-dione 
• 616898-64-7 oxo-[1-(1-pyridin-2-ylmethyl-piperidin-4-yl)-1H-indol-3-yl]-oxo-acetic acid methyl ester 

Relevant articles and documents

Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine

The polystyrene-cross-linking bisphosphine ligand PS-DPPBz was effective for the Ir-catalyzed reversible acceptorless dehydrogenation/hydrogenation of N-heterocycles. Notably, this protocol is applicable to the dehydrogenation of N-substituted indoline derivatives with various N-substituents with different electronic and steric natures. A reaction pathway involving oxidative addition of an N-adjacent C(sp3)-H bond to a bisphosphine-coordinated Ir(I) center is proposed for the dehydrogenation of N-substituted substrates.

[11C]Enzastaurin, the first design and radiosynthesis of a new potential PET agent for imaging of protein kinase C

Enzastaurin (LY317615) is a potent and selective protein kinase C (PKC) inhibitor with an IC50 value of ～6 nM. [11C] Enzastaurin (3-(1-[11C]methyl-1H-indol-3-yl)-4-[1-[1-(2- pyridinylmethyl)-4-piperidinyl]-1H-indol-3-yl]-1H-pyrrole-2,5-dione), a new potential PET agent for imaging of PKC, was first designed and synthesized in 20-25% decay corrected radiochemical yield and 370-555 GBq/μmol specific activity at end of bombardment (EOB). The synthetic strategy was to prepare a carbon-11-labeled maleic anhydride intermediate followed by the conversion to maleimide.

Strategies for the synthesis of N-(azacycloalkyl)bisindolylmaleimides: Selective inhibitors of PKCβ

N-(Azacycloalkyl)bisindolylmaleimides 1 have been identified to be selective inhibitors of PKCβ. This manuscript will describe the synthetic approaches employed to prepare this class of compounds that resulted in development of efficient methods for prepa