6208-43-1

Basic information

• Product Name: 2-Benzyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
• Synonyms: 2-Benzyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole;2-benzyl-1H,2H,3H,4H,5H-pyrido[4,3-b]indole
• CAS NO: 6208-43-1
• Molecular Formula: C₁₈H₁₈N₂
• Molecular Weight: 262.36
• Mol File: 6208-43-1.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 425°Cat760mmHg
• Flash Point: 210.8°C
• Appearance: /
• Density: 1.203g/cm³
• Vapor Pressure: 1.98E-07mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: 2-Benzyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Benzyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole(6208-43-1)
• EPA Substance Registry System: 2-Benzyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole(6208-43-1)

Safety Data

• Hazardous Substances Data: 6208-43-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H18N2/c1-2-6-14(7-3-1)12-20-11-10-18-16(13-20)15-8-4-5-9-17(15)19-18/h1-9,19H,10-13H2

Upstream product

• 3612-20-2 1-phenylmethyl-4-piperidone 
• 100-63-0 phenylhydrazine 
• 120656-71-5 N-(1-benzylpiperidin-4-ylidene)-N-(2-fluorophenyl)amine 
• 244-69-9 γ-carboline 
• 129303-82-8 1-phenyl-1H-[1,2,3]triazolo[4,5-c]pyridine 
• 59-88-1 phenylhydrazine hydrochloride 
• 1346446-51-2 (1-benzylpiperidin-4-ylidene)-(3-chlorophenyl)amine 
• 108-42-9 3-chloro-aniline 
• 1227476-15-4 Azobenzene 
• 100-39-0 benzyl bromide 

Downstream Products

• 81375-33-9 C₃₉H₄₂N₆ 
• 75487-78-4 2-Benzyl-5-(-3-dimethylaminopropyl)-1,2,3,4-tetrahydropyrido<4,3-b>indol 
• 69069-67-6 2-Benzyl-9b-chloro-2,3,4,9b-tetrahydro-1H-pyrido[4,3-b]indole 
• 95122-27-3 2-Benzyl-5-chloro-1,2,3,4-tetrahydro-pyrimido[1,6-a]indole 
• 1236142-54-3 5-benzoyl-2-benzyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride 
• 1332301-81-1 2-benzyl-5-ethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 
• 618910-03-5 5-ethyl-1H,2H,3H,4H,5H-pyrido[4,3-b]indole 
• 64996-21-0 1-benzyl-3-(2-oxo-2-phenyl-ethyl)-piperidin-4-one 
• 64996-24-3 5-benzyl-2-phenyl-4,5,6,7-tetrahydro-furo[3,2-c]pyridine 
• 64996-25-4 2-phenyl-4,5,6,7-tetrahydro-furo[3,2-c]pyridine 
• 1354547-56-0 methyl 4-((2-benzyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)benzoate 
• 933978-56-4 C₁₄H₁₈N₂ 

Relevant articles and documents

Evaluation of γ-carboline-phenothiazine conjugates as simultaneous NMDA receptor blockers and cholinesterase inhibitors

Alzheimer's disease (AD) is the most common form of dementia. It is associated with the impairment of memory and other cognitive functions that are mainly caused by progressive defects in cholinergic and glutamatergic signaling in the central nervous system. Inhibitors of acetylcholinesterase (AChE) and ionotropic glutamate receptors of the N-methyl-D-aspartate (NMDA) receptor family are currently approved as AD therapeutics. We previously showed using a cell-based assay of NMDA receptor-mediated glutamate-induced excitotoxicity that bis-γ-carbolinium conjugates are useful NMDA receptor blockers. However, these compounds also act as subnanomolar AChE inhibitors, which may cause serious anticholinergic side effects when applied in vivo. Here, we evaluated new structures containing γ-carbolines linked to phenothiazine via a propionyl spacer. These compounds were superior to the previously characterized bis-γ-carbolinium conjugates because they blocked NMDA receptors without requiring a quaternary pyridine N-atom and inhibited AChE with moderate IC50 values of 0.54–5.3 μM. In addition, these new compounds displayed considerable selectivity for the inhibition of butyrylcholinesterase (BChE; IC50 = 0.008–0.041 μM), which may be favorable for AD treatment. Inhibitory activities towards the NMDA receptors and AChE were in the same micromolar range, which may be beneficial for equal dosing against multiple targets in AD patients.

Double "open and Shut" Transformation of γ-Carbolines Triggered by Ammonium Salts: One-Pot Synthesis of Multiheterocyclic Compounds

A novel cascade reaction of indole-2,3-epoxide equivalents with γ-carbolines by utilizing a double "open and shut" transformation to access multiheterocyclic compounds containing both isotryptamines and pyrimido[1,6-a]indoles has been developed. This strategy utilizes the in situ formation of a bulky quaternary ammonium salt via ammonium exchange, which undergoes Hofmann elimination/vinylogous Mannich/retro-Mannich/cyclization cascade sequences.

Second-generation histone deacetylase 6 inhibitors enhance the immunosuppressive effects of Foxp3+ T-regulatory cells

Second-generation Tubastatin A analogues were synthesized and evaluated for their ability to inhibit selectively histone deacetylase 6 (HDAC6). Substitutions to the carboline cap group were well-tolerated with substitution at the 2-position of both β- and γ-carbolines being optimal for HDAC6 activity and selectivity. Some compounds in this series were determined to have subnanomolar activity at HDAC6 with more than 7000 fold selectivity for HDAC6 versus HDAC1. Selected compounds were then evaluated for their ability to augment the immunosuppressive effect of Foxp3+ regulatory T cells. All compounds tested were found to enhance the ability of regulatory T cells to inhibit the mitotic division of effector T cells both in vitro and in vivo, suggesting that further investigation into the use of these compounds for the treatment of autoimmune disorders is warranted.