1H-indole-3-carboxamide

Base Information

• Chemical Name: 1H-indole-3-carboxamide
• CAS No.: 1670-85-5
• Molecular Formula: C9H8 N2 O
• Molecular Weight: 160.175
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID90366920
• Nikkaji Number: J466.165F
• Wikidata: Q82152400
• Metabolomics Workbench ID: 71727
• ChEMBL ID: CHEMBL379099
• Mol file: 1670-85-5.mol

Synonyms:1H-indole-3-carboxamide;1H-Indole-3-carboxylic acid amide;1670-85-5;indole-3-carboxamide;1H-Indole-3-carboxamide(9CI);1-H-Indole-3-carboxamide;Cambridge id 5106715;MLS001048867;SCHEMBL117198;CHEMBL379099;BDBM93016;DTXSID90366920;LSGKMZLPZFPAIN-UHFFFAOYSA-N;HMS2268H20;MFCD00460642;STL561454;AKOS008997077;SDCCGMLS-0064613.P001;SMR000387070;CS-0063210;FT-0657418;EN300-49971;5P-052;C73221;I-2250;A810818;J-504702;Z87615024

Chemical Property of 1H-indole-3-carboxamide

Chemical Property:

• Melting Point: 201 °C
• Boiling Point: 457.6±18.0 °C(Predicted)
• PKA: 15.80±0.30(Predicted)
• PSA: 59.87000
• Density: 1.328±0.06 g/cm3(Predicted)
• LogP: 2.15100
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 160.063662883
• Heavy Atom Count: 12
• Complexity: 193

Purity/Quality:

97% ^*data from raw suppliers

1H-Indole-3-carboxylicAcidAmide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)C(=O)N
• General Description: 1H-Indole-3-carboxamide (9CI) is a structural derivative of indole featuring a carboxamide group at the 3-position, explored as a cannabinoid receptor agonist scaffold. In this study, modifications such as the introduction of a biphenyl moiety and replacement of the 3-carbonyl tether with a carboxamide linker were employed to optimize physicochemical properties, including lipophilicity and solubility, while targeting CB1 and CB2 receptors. These design strategies aimed to develop dual cannabinoid ligands with enhanced binding affinity and therapeutic potential for conditions like osteoporosis, neurodegeneration, and cancer. The carboxamide variant of indole, along with its azaindole bioisosteres, demonstrated promise in balancing receptor affinity and drug-like properties.

Technology Process of 1H-indole-3-carboxamide

There total 15 articles about 1H-indole-3-carboxamide 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: 98.0%

3-cyano-1H-indole (5457-28-3) → 1H-indole-3-carboxamide (1670-85-5)

Guidance literature:

With polystyrene-triethylenetetramine anchored ruthenium(II) complex; air; In water; at 90 ℃; for 7h; Green chemistry;

DOI:10.1002/aoc.3233

Reference yield: 92.0%

1H-indole-3-carboxylic acid (771-50-6) → 1H-indole-3-carboxamide (1670-85-5)

Guidance literature:

With ammonia; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; 1.) r.t., 0.5 h; 2.) 2 h;

DOI:10.1002/hlca.19940770719

Reference yield: 90.0%

Indole-3-carbonyl chloride (59496-25-2) → 1H-indole-3-carboxamide (1670-85-5)

Guidance literature:

With ammonia; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/S0031-9422(99)00479-3

upstream raw materials:

3-cyano-1H-indole

Indole-3-carbonyl chloride

2,2-dichloro-1-(1H-indol-3-yl)ethan-1-one

methyl imino ester hydrochloride of 3-indolecarboxylic acid

Downstream raw materials:

1H-indole-3-carboxylic acid

1H-indole-3-carbothioamide

1-p-toluenesulfonyl-1H-indole-3-carboxamide

3-aminomethylindole

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.