183581-91-1

Usage

Molecular structure

Methyl ester derivative of 1H-Indole-3-carboxylic acid
The compound is derived from 1H-Indole-3-carboxylic acid by replacing the hydrogen atom of the carboxylic acid group with a methyl ester group.

Indole ring

Presence of an indole ring in the structure
The compound contains an indole ring, which is a bicyclic aromatic structure consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Iodine atom

Contains an iodine atom in the 2-position
The compound has an iodine atom attached to the indole ring at the second position, which can influence its chemical reactivity and properties.

Phenylsulfonyl group

Presence of a phenylsulfonyl group in the structure
The compound contains a phenylsulfonyl group (a phenyl ring attached to a sulfonyl group) connected to the indole ring, which can contribute to its biological activity and synthetic utility.

Potential applications

Pharmaceutical research and organic synthesis
The compound has potential applications in the development of new drugs and biologically active molecules, as well as in the synthesis of various complex organic compounds.

Medicinal chemistry

Value as a building block and potential biological activities
Due to its structural characteristics, the compound is a valuable building block for the synthesis of other complex organic compounds and may exhibit biological activities that could be of interest for further investigation in the field of medicinal chemistry.

Upstream product

• 116325-17-8 N-benzenesulfonyl-1H-indole-3-carboxylic acid methyl ester 

Downstream Products

• 568571-30-2 methyl 2-iodo-1-(5-phenylpent-4-ynyl)-1H-indole-3-carboxylate 
• 482370-97-8 2-iodo-1-methoxymethyl-1H-indole-3-carboxylic acid allyl-phenyl-amide 

Relevant academic research and scientific papers

Identification of azepinone fused tetracyclic heterocycles as new chemotypes with protein kinase inhibitory activities

The design and synthesis of small tetracyclic heterocycles which bear two new regioisomeric 2-carboxyethyl-1H-pyrrole-annulated indoloazepinone scaffolds is described. An azepinone motif, which is inherent in the structures of many well studied protein kinase inhibitors, serves as prominent structural feature of the new compounds. Concise access to the new regioisomeric tetracyclic derivatives was accomplished through amide coupling of appropriate pyrrole and indole precursors followed by an intramolecular Heck coupling reaction of the intermediate amide conjugates. Preliminary evaluation of newly synthesized tetracyclic molecules against a panel of protein kinases indicated their inhibitory activities and revealed promising selectivity profiles. The new compounds displayed no significant antiproliferative activity against MCF-7 cancer cells. Interestingly, derivative 19a exhibited selective TAK1 kinase inhibitory activity and figures as a promising chemotype for the discovery of new TAK1 inhibitors.

Synthesis of annulated γ-carbolines and heteropolycycles by the palladium-catalyzed intramolecular annulation of alkynes

A variety of N-substituted 2-bromo-1H-indole-3-carboxaldehydes incorporating an alkyne-containing tether on the indole nitrogen have been converted to the corresponding tert-butylimines, which have been subjected to palladium-catalyzed intramolecular imin

Intramolecular Heck reaction of 2- and 3-iodoindole derivatives for the synthesis of β- and γ-carbolinones

A new synthesis of β- and γ-carbolinone derivatives was achieved by an intramolecular Heck cyclisation from the corresponding 3-iodo-1H-indole-2-carboxylic acid allyl-amides 8 and 2-iodo-1H-indole-3-carboxylic acid allyl-amides 9.

Magnesiation of indoles with magnesium amide bases

1-Substituted indole derivatives are deprotonated with Hauser bases (R2NMgBr) or magnesium diamide [(R2N)2-Mg] to give magnesioindoles which are then reacted with electrophiles.