18372-22-0

Usage

Uses

1. Used in Pharmaceutical Industry:
Methyl indolyl-3-glyoxylate is used as a reactant for the preparation of sotrastaurin analogs, which are protein kinase inhibitors. These inhibitors play a crucial role in regulating cellular processes and have potential applications in the treatment of various diseases, including cancer.
2. Used in Organic Synthesis:
Methyl indolyl-3-glyoxylate is used as a reactant for the synthesis of GSK-3 inhibitors. These inhibitors are essential in studying the role of glycogen synthase kinase-3 (GSK-3) in various cellular processes and may have therapeutic implications in treating conditions like Alzheimer's disease and type 2 diabetes.
3. Used in Chemical Research:
Methyl indolyl-3-glyoxylate is used as a reactant for Diels-Alder cycloaddition, a fundamental reaction in organic chemistry. This reaction is widely employed for the synthesis of complex organic molecules and has significant applications in the development of pharmaceuticals, agrochemicals, and materials.
4. Used in Medicinal Chemistry:
Methyl indolyl-3-glyoxylate is used as a reactant for the preparation of a Janus kinase 3 (JAK3) inhibitor. JAK3 inhibitors are being investigated for their potential in treating autoimmune diseases, inflammatory disorders, and certain types of cancer.
5. Used in Alkaloid Synthesis:
Methyl indolyl-3-glyoxylate is used as a reactant for the synthesis of cephalandole alkaloids, a class of natural products with diverse biological activities. These alkaloids have potential applications in the development of new drugs for the treatment of various diseases.
6. Used in Anticancer Research:
Methyl indolyl-3-glyoxylate is used as a reactant for the stereoselective preparation of COX-2 inhibitors, which are being studied for their potential as anticancer agents. COX-2 inhibitors may help in the treatment of cancer by reducing inflammation and inhibiting the growth of tumor cells.
7. Used in Organic Chemistry:
Methyl indolyl-3-glyoxylate is used as a reactant for the synthesis of cycloalkene indole carbazole alkaloids via ring-closing metathesis. This reaction is an essential tool in the construction of complex molecular structures and has applications in the development of novel pharmaceuticals and bioactive compounds.

InChI:InChI=1/C11H9NO3/c1-15-11(14)10(13)8-6-12-9-5-3-2-4-7(8)9/h2-6,12H,1H3

Upstream product

• 67-56-1 methanol 
• 22980-09-2 indolyl-3-glyoxylyl chloride 
• 5781-53-3 monomethyl oxalyl chloride 
• 120-72-9 indole 
• 1477-49-2 3-indolylglyoxylic acid 
• 124-41-4 sodium methylate 
• 79-37-8 oxalyl dichloride 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 527-31-1 hexaketocyclohexane 

Downstream Products

• 151490-40-3 methyl 2-(1-methyl-1H-indol-3-yl)-2-oxoacetate 
• 5548-10-7 indole-3-glyoxylamide 
• 110317-55-0 (E)-2-(3-Indolyl)-2-(hydroxyimino)essigsaeure-methylester 
• 110317-47-0 (Z)-2-(3-Indolyl)-2-(hydroxyimino)essigsaeure-methylester 
• 119139-23-0 3,4-bis(3-indolyl)-1H-pyrrole-2,5-dione 
• 133052-90-1 bisindolylmaleimide I 
• 203719-61-3 3-[1-(3-O'-triphenylmethylpropyl)-3-indolyl]-4-(3-indolyl)-1H-pyrrole-2,5-dione 
• 125313-57-7 3-(3-indolyl)-4-phenyl-1H-pyrrole-2,5-dione 
• 221377-35-1 3-(1H-indol-3-yl)-4-<7-chloro-1-<4-O-methyl-3,6-bis-O-(phenymethyl)-β-D-glucopyranosyl>-1H-indol-3-yl>-1H-pyrrole-2,5-dione 
• 220407-35-2 3-(1H-indol-3-yl)-4-(1-trityl-1H-imidazol-4-yl)-pyrrole-2,5-dione 
• 29095-44-1 2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide 
• 244086-64-4 isodidemnimide A 
• 113975-75-0 methyl indol-3-ylglyoxylate oxime 
• 203719-73-7 4-[1-(2-{3-hydroxy-1-[(triphenylmethoxy)methyl]propoxy}ethyl)indol-3-yl]-3-(indol-3-yl)-3-pyrroline-2,5-dione 

Relevant academic research and scientific papers

Design, synthesis and evaluation of novel (S)-tryptamine derivatives containing an allyl group and an aryl sulfonamide unit as anticancer agents

A series of (S)-tryptamine derivatives containing an allyl group and an aryl sulfonamide unit were designed, synthesized and evaluated for their potential application as anticancer agents. The structures of the synthesized compounds were characterized by 1H NMR, 13C NMR and ESI-MS spectral analyses. The target compounds were evaluated for their in vitro cytotoxicity against HepG2, HeLa, CNE1 and A549 human cancer cell lines. Some of the synthesized compounds showed moderate to good anticancer activities against four selected cancer cell lines, among of which 6ag was found to be the most active analogue possessing IC50 values 16.5–18.7 μM. Further mechanism studies revealed that compound 6ag could significantly induce HepG2 cell cycle arrest at G1 phase, promote cell apoptosis, and inhibit the colony formation as well.

Copper-catalyzed carbonylative transformations of indoles with hexaketocyclohexane

With hexaketocyclohexane octahydrate as the carbon monoxide source, a novel procedure for copper-catalyzed direct double carbonylation of indoles has been established. Using alcohols as reaction partners, moderate to good yields of the desired double carbonylation products have been obtained. Wide functional group tolerance and substrate scope can be observed.

Concise synthesis of the (±)-Nb-desmethyl-meso- chimonanthine

The first total synthesis of the bis-pyrroloindoline alkaloid (±)-Nb-desmethyl-meso-chimonanthine, having a pseudo C 2-symmetry, was realised in a seven-step convergent sequence without the use of protecting groups. The Royal Society of Chemistry 2006.

S -indole benzamide derivative as well as preparation method and application thereof

S - Indole benzamide derivatives as well as a preparation method and application thereof relate to the technical field of pharmacy. The derivative has a structural formula. The specific preparation method comprises the following steps: taking indole as a starting raw material and performing acylation reaction. Reaction, oxidation reaction, (R)- (+) -tert-butylsulfenamide asymmetric synthesis reaction, hydrolysis reaction and acylation reaction to give the target product. By means of the method, a novel antiviral drug with a development prospect can be obtained, and the yield is high.

3-(7-Azaindolyl)-4-indolylmaleimides as a novel class of mutant isocitrate dehydrogenase-1 inhibitors: Design, synthesis, and biological evaluation

A series of 3-(7-azainodyl)-4-indolylmaleimides was designed, synthesized, and evaluated for their isocitrate dehydrogenase 1 (IDH1)/R132H inhibitory activities. Many compounds such as 11a, 11c, 11e, 11g, and 11s exhibited favorable inhibitory effects on IDH1/R132H and were highly selective against the wild-type IDH1. Evaluation of the biological activities at the cellular level showed that compounds 11a, 11c, 11e, 11g, and 11s could effectively suppress the production of 2-hydroxyglutaric acid in U87MG cells expressing IDH1/R132H. Preliminary structure–activity relationship (SAR) and molecular modeling studies were discussed based on the experimental data obtained. These findings may provide new insights into the development of novel IDH1/R132H inhibitors.

A convenient synthesis of indole and 1,4-dihydropyridine hybrid macromolecules by dimerization of [2-(1h-indol-3-yl)ethyl]pyridinium salts

The design and synthesis of a novel type of macrocyclic compounds containing indole and 1,4-dihydropyridine heterocyclic subunits is presented. The key reaction involved in the synthesis was a base-mediated dimerization of [2-(1H-indol-3-yl)ethyl]pyridinium salts. The structure of the macrocycles was unambiguously confirmed by NMR and HRMS spectroscopic and X-ray single crystal diffraction.

Synthesis and properties of novel heat-resistant fluorescent conjugated polymers with bisindolylmaleimide

Conjugated polymers with bisindolylmaleimide (BIM) backbone are obtained by the condensation polymerization of methyl and octanyl N-substituted BIMs with 4,4'-difluoro-diphenylsulfone and 4,4'-difluoro-diphenylketone. The structures of polymers are confirmed by FTIR and NMR spectroscopy. The polymers exhibit both high glass transition temperatures (Tg > 175 °C) and high decomposition temperatures (T5 > 395 °C). Meanwhile, The UV–vis absorption and fluorescence spectra of the polymers are similar to the corresponding substituted BIMs. The quantum chemistry calculations indicate that the first excited states of polymers are mostly contributed by BIM structures.

An indole-based conjugated microporous polymer: A new and stable lithium storage anode with high capacity and long life induced by cation-π interactions and a N-rich aromatic structure

An indole-based conjugated microporous polymer, poly(bisindolylmaleimide) (PBIM), with superior electrochemical performance as an anode material for LIBs has been obtained by FeCl3-promoted oxidative coupling polymerization. Benefiting from reversible cation-π interactions and a unique aromatic structure containing N heteroatoms, the prepared PBIM anode shows high capacity (1172 mA h g-1, 50 mA g-1), outstanding cycle life (1000 cycles), and remarkable rate performance (214 mA h g-1, 2.5C).

[18F]MALEIMIDE-BASED GLYCOGEN SYNTHASE KINASE-3BETA LIGANDS FOR POSITRON EMISSION TOMOGRAPHY IMAGING AND RADIOSYNTHESIS METHOD

The present invention provides a compound having the structure: (Formula I), and a method of inhibiting Glycogen synthase kinase-3 β (GSK-3β) in a subject comprising administering to the subject said compound, so as to thereby inhibit the GSK-3β in the subject.

Design and synthesis of (aza)indolyl maleimide-based covalent inhibitors of glycogen synthase kinase 3β

As an important kinase in multiple signal transduction pathways, GSK-3β has been an attractive target for chemical probe discovery and drug development. Compared to numerous reversible inhibitors that have been developed, covalent inhibitors of GSK-3β are