172595-68-5

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 5-methoxy-1H-indole-3-carboxylate is used as a reactant for the synthesis of tetrahydropyridoindoles, which are important compounds in the development of novel pharmaceuticals. The synthesis is facilitated through a ruthenium-catalyzed decarboxylative C-H alkenylation process, which allows for the formation of complex molecular structures with potential therapeutic applications.
Used in Chemical Industry:
In the chemical industry, Methyl 5-methoxy-1H-indole-3-carboxylate is utilized as a building block for the creation of various indole-based compounds. These compounds can be further modified and functionalized to serve as intermediates in the synthesis of a wide range of products, including dyes, pigments, and other specialty chemicals. The versatility of Methyl 5-methoxy-1H-indole-3-carboxylate makes it a valuable asset in the development of new materials and applications.

InChI:InChI=1/C11H11NO3/c1-14-7-3-4-10-8(5-7)9(6-12-10)11(13)15-2/h3-6,12H,1-2H3

Upstream product

• 7424-91-1 methyl 3,3-dimethoxypropionate 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 67-56-1 methanol 
• 1006-94-6 5-methoxylindole 
• 76-02-8 trifluoroacetyl chloride 
• 391277-53-5 methyl 2-(5-methoxy-2-nitrophenyl)acrylate 
• 10242-01-0 5-Methoxyindole-3-carboxylic acid 
• 30030-92-3 2,2,2-trichloro-1-(5-methoxy-1H-indol-3-yl)ethan-1-one 
• 100-17-4 para-methoxynitrobenzene 
• 4546-20-7 p-methoxyphenylhydroxylamine 
• 922-67-8 propynoic acid methyl ester 

Downstream Products

• 1215118-62-9 2-(2-(3,5-bis-(trifluoromethyl)benzyloxy)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetic acid 
• 10242-01-0 5-Methoxyindole-3-carboxylic acid 

Relevant academic research and scientific papers

Formation and trapping of azafulvene intermediates derived from manganese-mediated oxidative malonate coupling

The one-pot, three-component, coupling reaction of indoles/pyrroles, dimethyl malonate, and acetic acid was performed using Mn(III) acetate as an oxidant. In the presence of Mn(OAc)3, indole-2, and indole-3-carbonyl compounds were alkylated at the 3- and 2- positions, respectively, with subsequent oxidation and nucleophilic capture occurring at the newly formed benzylic carbon. In contrast, oxidation of 2- and 3-indole carboxylic acids afforded the corresponding 2-oxindol-3-ylidenes and 3-oxindol-2-ylidenes. The reaction conditions, scope, and mechanism are discussed herein.

Development and Profiling of Inverse Agonist Tools for the Neuroprotective Transcription Factor Nurr1

The ligand-sensing transcription factor nuclear receptor related 1 (Nurr1) evolves as an appealing target to treat neurodegenerative diseases. Despite its therapeutic potential observed in various rodent models, potent modulators for Nurr1 are lacking as pharmacological tools. Here, we report the structure-activity relationship and systematic optimization of indole-based inverse Nurr1 agonists. Optimized analogues decreased the receptor's intrinsic transcriptional activity by up to more than 90% and revealed preference for inhibiting Nurr1 monomer activity. In orthogonal cell-free settings, we detected displacement of NCoRs and disruption of the Nurr1 homodimer as molecular modes of action. The inverse Nurr1 agonists reduced the expression of Nurr1-regulated genes in T98G cells, and treatment with an inverse Nurr1 agonist mimicked the effect of Nurr1 silencing on interleukin-6 release from LPS-stimulated human astrocytes. The indole-based inverse Nurr1 agonists valuably extend the toolbox of Nurr1 modulators to further probe the role of Nurr1 in neuroinflammation, cancer, and beyond.

A general and scalable synthesis of polysubstituted indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

Amination/Cyclization Cascade by Acid-Catalyzed Activation of Indolenine for the One-Pot Synthesis of Phaitanthrin E

We have developed a concise one-pot synthesis of phaitanthrin E derivatives, where simple starting materials undergo an acid-catalyzed intermolecular amination/intramolecular cyclization cascade.

Ionic diamine rhodium complex catalyzed reductive N-heterocyclization of 2-nitrovinylarenes

Ionic diamine rhodium complex (1) catalyzes the reductive N-cyclization of 2-vinylnitroarenes using carbon monoxide as a reducing agent to afford functionalized indoles. The catalytic system allows direct access to indoles with ester and ketone groups at the 2- or 3-position, in good yields.

Catalytic enantioselective Meerwein-Eschenmoser Claisen rearrangement: Asymmetric synthesis of allyl oxindoles

The first catalytic, enantioselective Meerwein-Eschenmoser Claisen rearrangement has been achieved. Palladium(II) BINAP or phosphinooxazoline catalysts were employed to generate oxindole products with 100% conversion and up to 92% ee. Copyright

COMPOUND INHIBITING DIPEPTIDYL PEPTIDASE IV

The invention aims to provide a dipeptidyl peptidase IV inhibitor which is satisfactory in respect of activity, stability and safety and has an excellent action as a pharmaceutical agent. The invention is directed to a compound represented by the following general formula or a pharmaceutically acceptable salt thereof: wherein R1 and R2 each represents hydrogen, an optionally substituted C1-6 alkyl group, or -COOR5 whereupon R5 represents hydrogen or an optionally substituted C1-6 alkyl group, or R1 and R2, together with a carbon atom to which they are bound, represent a 3- to 6-membered cycloalkyl group, R3 represents hydrogen or an optionally substituted C6-10 aryl group, R4 represents a hydrogen or a cyano group, D represents -CONR6-, -CO- or -NR6CO-, R6 represents hydrogen or an optionally substituted C1-6 alkyl group, E represents -(CH2)m- whereupon m is an integer of 1 to 3, -CH2OCH2-, or -SCH2-, n is an integer of 0 to 3, and A represents an optionally substituted bicyclic heterocyclic group or bicyclic hydrocarbon group.