1H-Indole-2-carboxamide

Base Information

• Chemical Name: 1H-Indole-2-carboxamide
• CAS No.: 1670-84-4
• Molecular Formula: C9H8N2O
• Molecular Weight: 160.175
• Hs Code.: 2933990090
• European Community (EC) Number: 605-465-9
• DSSTox Substance ID: DTXSID50344168
• Nikkaji Number: J1.605.355D
• Wikidata: Q82115846
• Mol file: 1670-84-4.mol

Synonyms:1H-Indole-2-carboxamide;1670-84-4;Indole-2-carboxamide;1H-Indole-2-carboxylic acid amide;MFCD00231036;Indole, 2-carboxamide-;3H-Indole-2-carboxamide;Indole amide;indoleimidocarboxylic;2-indole carboxamide;1H-2-indolecarboxamide;1H-Indole-2-carboxamide #;SCHEMBL118686;indole-2-carboxylic acid amide;BDBM93014;DTXSID50344168;BAA67084;STK504767;AKOS000430477;SY225211;CS-0149972;FT-0679355;4P-033;F53644;A850056;W-205961;Z101185700;N-(N-TRIFLUOROACETYL-L-CYSTEINYL)-GLYCINEMETHYLESTER

Chemical Property of 1H-Indole-2-carboxamide

Chemical Property:

• Vapor Pressure: 1.47E-08mmHg at 25°C
• Melting Point: 234.5-235.5 °C
• Refractive Index: 1.716
• Boiling Point: 457.6 °C at 760 mmHg
• PKA: 15.39±0.30(Predicted)
• Flash Point: 230.6 °C
• PSA: 58.88000
• Density: 1.328 g/cm³
• LogP: 1.96710
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• 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-2-carboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(N2)C(=O)N
• General Description: Indole-2-carboxamide derivatives, such as N-cyclooctyl-6-trifluoromethylindol-2ylmethylamine, demonstrate potent mycobactericidal activity against *Mycobacterium tuberculosis* by targeting the mycolate transporter MmpL3, while structural modifications like amide-amine replacement significantly improve water solubility without reducing efficacy.

Technology Process of 1H-Indole-2-carboxamide

There total 24 articles about 1H-Indole-2-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: 97.0%

3-(2-nitrophenyl)pyruvic acid amide → 1H-indole-2-carboxamide (1670-84-4)

Guidance literature:

With sodium dithionite; In 1,4-dioxane; water; for 3h; Reflux;

DOI:10.1016/j.tetlet.2018.09.039

Reference yield: 90.0%

Indole-2-carboxylic acid (1477-50-5,1228050-17-6) → 1H-indole-2-carboxamide (1670-84-4)

Guidance literature:

Indole-2-carboxylic acid; With thionyl chloride; N,N-dimethyl-formamide; In chloroform; for 2h; Heating / reflux;

With ammonia; In chloroform; water; at 20 ℃; for 2h;

Reference yield: 89.0%

(Z)-3-(2-aminophenyl)-2-bromoacrylamide (1586740-74-0) → 1H-indole-2-carboxamide (1670-84-4)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide; potassium carbonate; In 1,4-dioxane; for 2h; Schlenk technique; Inert atmosphere; Reflux;

DOI:10.1016/j.tetlet.2013.10.048

upstream raw materials:

Indole-2-carbonyl chloride

indole-2-carboxylic acid methyl ester

2-((E)-phenylhydrazono)-propionic acid amide

2-carbethoxyindole

Downstream raw materials:

1-(1H-indol-2-yl)methanamine

2-(4-methylbenzoylaminomethyl)indole

2-(2-fluorobenzoylaminomethyl)indole

2-(thiobenzoylaminomethyl)indole

Refernces

Amide-Amine Replacement in Indole-2-carboxamides Yields Potent Mycobactericidal Agents with Improved Water Solubility

10.1021/acsmedchemlett.0c00588

The study explores modifications to the indole-2-carboxamide scaffold to improve the solubility and potency of mycobactericidal agents against Mycobacterium tuberculosis (M. tb). The researchers found that replacing the carboxamide linker with a protonatable aminomethyl side chain, and substituting the indole ring with benzothiophene or benzoselenophene, led to significant improvements in solubility (10-20-fold) without compromising potency. The indolylmethylamine compound 33 (N-cyclooctyl-6-trifluoromethylindol-2ylmethylamine) emerged as a promising candidate with a MIC90 of 0.13 μM against M. tb and MBC99.9 of 0.63 μM, showing comparable activity to its carboxamide equivalent. This compound also inhibited the mycolate transporter MmpL3, a key target for several indolecarboxamides. The study highlights the potential of these structural modifications to enhance the therapeutic potential of indole-based mycobactericidal agents.