1H-pyrrolo[3,2-b]pyridine

Base Information

• Chemical Name: 1H-pyrrolo[3,2-b]pyridine
• CAS No.: 272-49-1
• Molecular Formula: C7H6N2
• Molecular Weight: 118.138
• Hs Code.: 29339980
• European Community (EC) Number: 674-574-1
• DSSTox Substance ID: DTXSID00181666
• Nikkaji Number: J2.252.650B,J72.955H
• Wikidata: Q27454752
• Mol file: 272-49-1.mol

Synonyms:4-azaindole

Chemical Property of 1H-pyrrolo[3,2-b]pyridine

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 0.009mmHg at 25°C
• Melting Point: 126-127 °C
• Refractive Index: 1.697
• Boiling Point: 273.782 °C at 760 mmHg
• PKA: 14.66±0.30(Predicted)
• Flash Point: 124.839 °C
• PSA: 28.68000
• Density: 1.242 g/cm³
• LogP: 1.56290
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility.: Soluble in methanol and chloroform. Slightly soluble in water.
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 118.053098200
• Heavy Atom Count: 9
• Complexity: 103

Purity/Quality:

99% ^*data from raw suppliers

4-Azaindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CN2)N=C1
• General Description: 4-Azaindole (1H-pyrrolo[3,2-b]pyridine) is a bioisostere of indole, featuring a nitrogen atom at the 4-position of the indole scaffold. It has been explored in medicinal chemistry as a structural modification to enhance lipophilicity and aqueous solubility in the design of cannabinoid receptor agonists. Its incorporation into ligands targeting CB1 and CB2 receptors aims to improve physicochemical properties while maintaining or enhancing receptor binding affinity, making it a valuable scaffold for developing therapeutic agents in conditions such as pain, inflammation, and neurodegenerative diseases.

Technology Process of 1H-pyrrolo[3,2-b]pyridine

There total 29 articles about 1H-pyrrolo[3,2-b]pyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-(1H-pyrrolo[3,2-b]pyridin-1-yl)ethanone (24509-73-7) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Guidance literature:

With potassium carbonate; In methanol;

DOI:10.1021/ol900150u

Reference yield: 97.0%

2-((trimethylsilyl)ethynyl)pyridin-3-amine (947330-64-5) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; acetonitrile; at 20 ℃; for 2h;

Reference yield: 95.0%

2-(3-nitro-2-pyridinyl)-N,N-dimethyletheneamine (65156-92-5,343569-94-8) → 1H-pyrrolo[3,2-b]pyridine (272-49-1)

Guidance literature:

With hydrogen; palladium on activated charcoal;

upstream raw materials:

N-(2-methyl-[3]pyridyl)-formamide

potassium ethoxide

2-chloro-3-aminopyridine

acetaldehyde

Downstream raw materials:

3-bromo-1H-pyrrolo[3,2-b]pyridine

tert-butyl 3-bromo-1H-pyrrolo[3,2-b]pyridine-1-carboxylate

1H-pyrrolo[3,2-b]pyridine-3-carbaldehyde

1H-pyrrolo[3,2-b]pyridine-1-carboxylic acid 1,1-dimethylethyl ester

Refernces

Novel indole and azaindole (pyrrolopyridine) cannabinoid (CB) receptor agonists: Design, synthesis, structure-activity relationships, physicochemical properties and biological activity

10.1016/j.ejmech.2011.08.021

The study presents the design, synthesis, and evaluation of a novel series of indole and azaindole (pyrrolopyridine) cannabinoid (CB) receptor agonists. These compounds were developed to target cannabinoid 1 (CB1) and cannabinoid 2 (CB2) receptors, which are G protein-coupled receptors involved in various physiological processes and have therapeutic potential in conditions such as osteoporosis, multiple sclerosis, Alzheimer's disease, and cancer, among others. The researchers introduced a biphenyl moiety as a novel lipophilic indole 3-acyl substituent and replaced the 3-carbonyl tether with a carboxamide linker to improve physicochemical properties. They also designed azaindole (pyrrolopyridine) nuclei as indole bioisosteres to enhance lipophilicity and aqueous solubility. The purpose of these chemical modifications was to identify high-affinity CB1/CB2 dual cannabinoid receptor ligands with improved physicochemical properties, which could lead to more effective therapeutic agents. The study involved the synthesis and testing of various compounds, including indole-3-carboxamide derivatives and azaindoles, to evaluate their binding affinity, functional activity, and selectivity for CB1 and CB2 receptors.

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