98323-95-6

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

• 24078-21-5 methyl 3-methyl-4-nitrobenzoate 
• 108763-41-3 methyl (E)-3-(2-(dimethylamino)vinyl)-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

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

Relevant academic research and scientific papers

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.

Anti-Cytokine Heterocyclic Compounds

Heterocyclic compounds and analogues thereof and their use as inhibitors of Mitogen-Activated Protein Kinase-Activated Protein kinase-2 (MAPKAP-k2), and also to a method for preventing or treating a disease or disorder that can be treated or prevented by

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).