59549-49-4

Usage

Uses

Used in Pharmaceutical Industry:
5,7-DIMETHYL-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER is used as a chemical intermediate for the synthesis of antiarrhythmic compounds. Its role in the development of these medications is crucial, as it contributes to the regulation of heart rhythm and the prevention of abnormal electrical activity in the heart.
Additionally, 5,7-DIMETHYL-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER is used as a reactant in the synthesis of anti-convulsants. These medications are essential for the treatment of epilepsy and other conditions characterized by recurrent seizures, as they help to control the electrical activity in the brain and prevent the onset of convulsions.

Upstream product

• 133131-70-1 2-(2,4-dimethyl-phenylhydrazono)-propionic acid ethyl ester 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 60480-83-3 (2,4-dimethylphenyl)hydrazine hydrochloride 
• 100876-06-0 2-mesitylhydrazono-propionic acid ethyl ester 
• 70335-45-4 2,4,6-trimethylphenyl diazonium chloride 
• 60481-36-9 (3,5-dimethylphenyl)hydrazine hydrochloride 

Downstream Products

• 221675-45-2 5,7-dimethyl-1H-indole-2-carboxylic acid 
• 883016-34-0 N-cyclohexyl-4,6-dimethyl-1H-indole-2-carboxamide 

Relevant academic research and scientific papers

Design, synthesis and evaluation of indole-2-carboxamides with pan anti-mycobacterial activity

Current treatment regimens for non-tuberculous mycobacteria (NTM) and tuberculosis (TB) generally require long duration of therapy with multiple drugs, some of which are broad spectrum antibiotics. Despite some advances in antimicrobial compounds, there remains a need in therapy for antibiotics with specific mycobacterial targets. It has been shown that MmpL3 is an essential transporter required for the translocation of mycolic acids to the mycobacterial cell envelope. Here, we synthesized a series of indole-2-carboxamides that inhibit MmpL3 and have potent pan-activity against mycobacterial species. The compounds were tested against several fast and slow-growing Mycobacterium species, including M. abscessus, M. massiliense, M. bolletii, M. chelonae, M. tuberculosis, M. avium, M. xenopi and M. smegmatis. The target of these indole-based compounds makes them selective for mycobacteria, while showing no clinically relevant bactericidal activity against S. aureus or P. aeruginosa. These compounds were tested against THP-1, a human-cell line, and showed minimal in vitro cytotoxicity and good selectivity indices. The data shown and discussed suggest that lead indole-2-carboxamides are strong contenders for further preclinical testing as NTM therapeutics.

Fischer indolisation of 2,6-dialkyl and 2,4,6-trialkylphenylhydrazones of diketones and ketoesters

Unlike the migration of a methyl group observed in the ZnCl2 or acetic acid-catalysed indolisation of phenylhydrazones, dry ethanolic HCl catalysed indolisation of 2,6-dimethyl- and 2,4,6-trimethylphenylhydrazones of various substituted butane-2,3-diones and ethyl pyruvates yields 7-methyl- and 5,7-dimethyl-3-substituted indoles indicating elimination of an ortho-methyl group during indolisation.

The first potent and selective non-imidazole human histamine H4 receptor antagonists

Following the discovery of the human histamine H4 receptor, a high throughput screen of our corporate compound collection identified compound 6 as a potential lead. Investigation of the SAR resulted in the discovery of novel compounds 10e and 10l, which are the first potent and selective histamine H4 receptor antagonists to be described.