98323-95-6

Basic information

• Product Name: 1H-Indole-5-carboxylic acid, 3-[(dimethylamino)methyl]-, methyl ester
• CAS NO: 98323-95-6
• Molecular Formula: C13H16N2O2
• Molecular Weight: 232.282
• Mol File: 98323-95-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1H-Indole-5-carboxylic acid, 3-[(dimethylamino)methyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-5-carboxylic acid, 3-[(dimethylamino)methyl]-, methyl ester(98323-95-6)
• EPA Substance Registry System: 1H-Indole-5-carboxylic acid, 3-[(dimethylamino)methyl]-, methyl ester(98323-95-6)

Safety Data

• Hazardous Substances Data: 98323-95-6(Hazardous Substances Data)

Usage

Molecular class

Indole carboxylic acid derivative

Structure

Methyl ester of 1H-indole-5-carboxylic acid with a dimethylamino functional group

Potential applications

Pharmaceutical and agrochemical industries

Biological activities

Anti-inflammatory, antibacterial, and anticancer properties

Usage

Building block in the synthesis of diverse organic molecules and pharmaceutical compounds

Importance

Unique chemical structure and biological activities make it a valuable compound for further research and development in medicine and agriculture.

Upstream product

• 108763-41-3 methyl (E)-3-(2-(dimethylamino)vinyl)-4-nitrobenzoate 
• 24078-21-5 methyl 3-methyl-4-nitrobenzoate 
• 3113-71-1 3-methyl-4-nitrobenzoic acid 
• 50-00-0 formaldehyd 
• 1011-65-0 5-methoxycarbonylindole 
• 124-40-3 dimethyl amine 

Downstream Products

• 916520-95-1 N-phenyl 4,4-spirocyclobutyl-1-oxo-2,3,4,9-tetrahydro-1H-1-carboline-6-carboxamide 
• 113438-59-8 3-cyanomethyl-1H-indole-5-carboxylic acid methyl ester 
• 1026364-20-4 1-[3-(4-Benzhydryl-piperazin-1-yl)-propyl]-3-imidazol-1-ylmethyl-1H-indole-5-carboxylic acid methyl ester 

Relevant articles and documents

Catalyst-Controlled Regiodivergence in Rearrangements of Indole-Based Onium Ylides

We have developed catalyst-controlled regiodivergent rearrangements of onium-ylides derived from indole substrates. Oxonium ylides formed in situ from substituted indoles selectively undergo [2,3]- and [1,2]-rearrangements in the presence of a rhodium and a copper catalyst, respectively. The combined experimental and density functional theory (DFT) computational studies indicate divergent mechanistic pathways involving a metal-free ylide in the rhodium catalyzed reaction favoring [2,3]-rearrangement, and a metal-coordinated ion-pair in the copper catalyzed [1,2]-rearrangement that recombines in the solvent-cage. The application of our methodology was demonstrated in the first total synthesis of the indole alkaloid (±)-sorazolon B, which enabled the stereochemical reassignment of the natural product. Further functional group transformations of the rearrangement products to generate valuable synthetic intermediates were also demonstrated.

Thromboxane A2 synthetase inhibitors with histamine H1-blocking activity: Synthesis and evaluation of a new series of indole derivatives

A novel series of N-substituted 3-(1H-imidazol-1-ylmethyl)indole carboxylic acid derivatives were prepared and evaluated for thromboxane A2 (TXA2) synthetase-inhibitory and histaminergic H1-blocking activity. Among the compounds synthesized, indole-6-carboxylic acid derivatives showed higher activities than the other positional isomers of carboxylic acid. 1-[3-(4- Benzhydryl-1-piperazinyl)propyl]-3-(1H-imidazol-1-ylmethyl)-1H-indole-6- carboxylic acid (12) had the strongest thromboxane synthetase inhibitory activity (IC50 = 5 x 10-8 M) and H1-blocking activity (IC50 = 8 x 10- 9 M).