151490-40-3

Basic information

• Product Name: 2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER
• Synonyms: METHYL 2-(1-METHYL-1H-INDOLE-3-YL)-2-OXOACETATE;METHYL (1-METHYLINDOLYL)-3-GLYOXYLATE;2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER;METHYL (1-METHYLINDOLYL-3)-GLYOXYLATE, 9;Methyl (1-methylindolyl)-3-glyoxylate 97%;methyl 2-(1-methyl-1H-indol-3-yl)-2-oxoacetate
• CAS NO: 151490-40-3
• Molecular Formula: C₁₂H₁₁NO₃
• Molecular Weight: 217.22
• Product Categories: Aromatic Esters;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 151490-40-3.mol

Chemical Properties

• Melting Point: 96-100 °C(lit.)
• Boiling Point: 369.9°C at 760 mmHg
• Flash Point: 177.5°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 1.15E-05mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: 2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER(151490-40-3)
• EPA Substance Registry System: 2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER(151490-40-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 151490-40-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER is used as a reactant for the synthesis of sotrastaurin analogs for its role in the development of novel protein kinase C (PKC) inhibitors. These inhibitors are crucial in the treatment of various diseases, including cancer and autoimmune disorders, due to their ability to modulate cellular signaling pathways.
Used in Chemical Synthesis:
In the chemical synthesis industry, 2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER serves as a reactant for the preparation of indolyl diols. These compounds have potential applications in the development of new drugs and materials, thanks to their unique chemical properties and reactivity.
Overall, 2-(1-METHYL-1H-INDOL-3-YL)-2-OXOACETIC ACID METHYL ESTER is a valuable compound in both the pharmaceutical and chemical synthesis industries, owing to its diverse applications and the potential for further research and development in these fields.

InChI:InChI=1/C12H11NO3/c1-13-7-9(11(14)12(15)16-2)8-5-3-4-6-10(8)13/h3-7H,1-2H3

Upstream product

• 18372-22-0 2-(3-indolyl)oxoacetic acid methyl ester 
• 74-88-4 methyl iodide 
• 603-76-9 1-methylindole 
• 79-37-8 oxalyl dichloride 
• 124-41-4 sodium methylate 
• 22980-09-2 indolyl-3-glyoxylyl chloride 
• 120-72-9 indole 
• 16382-38-0 1-methylindole-3-glyoxylyl chloride 
• 41600-21-9 methyl 2-oxo-2-(pyrrolidin-1-yl)acetate 

Downstream Products

• 170364-57-5 enzastaurin 
• 125314-02-5 3-(4-aminophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione 
• 125314-13-8 3-(3-aminophenyl)-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione 
• 125313-99-7 3-(4-chlorophenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione 
• 1262304-44-8 4-(4-(4-(4-(3-(4-(1-methyl-1H-indol-3-yl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-indol-1-yl)-butyl)-(1,2,3)triazol-1-yl)-phenyl)-butyric acid 

Relevant articles and documents

Synthesis and Evaluation of 3-(furo[2,3-b]pyridin-3-yl)-4-(1H-indol-3-yl)-maleimides as Novel GSK-3β Inhibitors and Anti-Ischemic Agents

A series of novel 3-(furo[2,3-b]pyridin-3-yl)-4-(1H-indol-3-yl)-maleimides were designed, synthesized, and biologically evaluated for their GSK-3β inhibitory activities. Most compounds showed favorable inhibitory activities against GSK-3β protein. Among them, compounds 5n, 5o, and 5p significantly reduced GSK-3β substrate tau phosphorylation at Ser396 in primary neurons, indicating inhibition of cellular GSK-3β activity. In the in vitro neuronal injury models, compounds 5n, 5o, and 5p prevented neuronal death against glutamate, oxygen-glucose deprivation, and nutrient serum deprivation which are closely associated with cerebral ischemic stroke. In the in vivo cerebral ischemia animal model, compound 5o reduced infarct size by 10% and improved the neurological deficit. The results may provide new insights into the development of novel GSK-3β inhibitors with potential neuroprotective activity against brain ischemic stroke.

Design, synthesis, and evaluation of 3-aryl-4-pyrrolyl-maleimides as glycogen synthase kinase-3β inhibitors

A series of 3-aryl-4-pyrrolyl-maleimides were designed, synthesized, and evaluated for their glycogen synthase kinase-3β (GSK-3β) inhibitory activity. Most compounds exhibited potent activity against GSK-3β. Among them, compounds 11a, 11c, 11h, 11i, and 11j significantly reduced Aβ-induced Tau hyperphosphorylation, showing the inhibition of GSK-3β at the cellular level. Structure-activity relationships were discussed based on the experimental data obtained. Most compounds in a new series of 3-aryl-4-pyrrolyl-maleimides exhibited potent glycogen synthase kinase-3β (GSK-3β) inhibitory activity. Compounds 11a, 11c, 11h, 11i, and 11j reduced Aβ-induced Tau hyperphosphorylation, showing inhibition of GSK-3β at the cellular level. Copyright

Discovery of an Orally Available Janus Kinase 3 Selective Covalent Inhibitor

JAK family kinases are important mediators of immune cell signaling and Janus Kinase 3 (JAK3) has long been indicated as a potential target for autoimmune disorders. Intensive efforts to develop highly selective JAK3 inhibitors have been underway for many years. However, because of JAK3's strong binding preference to adenosine 5′-triphosphate (ATP), a number of inhibitors exhibit large gaps between enzymatic and cellular potency, which hampers efforts to dissect the roles of JAK3 in cellular settings. Using a targeted covalent inhibitor approach, we discovered compound 32, which overcame ATP competition (1 mM) in the enzymatic assay, and demonstrated significantly improved inhibitory activity for JAK3-dependent signaling in mouse CTLL-2 and human peripheral blood mononuclear cells. Compound 32 also exhibited high selectivity within the JAK family and good pharmacokinetic properties. Thus, it may serve as a highly valuable tool molecule to study the overlapping roles of JAK family kinases in complex biological settings. Our study also suggested that for covalent kinase inhibitors, especially those targeting kinases with low Km ATP values, the reversible interactions between molecules and proteins should be carefully optimized to improve the overall potency.

Method for continuously preparing 3,4-(1-methyl-indol-3-yl)-1H-pyrrole-2,5-one compound by microchannel reactor

The invention discloses a method for continuously preparing a 3,4-(1-methyl-indol-3-yl)-1H-pyrrole-2,5-one compound by a microchannel reactor. The method comprises the following steps: dissolving 1-methyl-3-indole acetamide and 1-methyl indolo ketonic acid methyl ester into anhydrous dimethylformamide (DMF) to form a mixed solution which is a solution A; dissolving potassium tert-butoxide in anhydrous DMF, and uniformly carrying out mixing to obtain a solution B; and feeding the prepared solution A and the prepared solution B into the microchannel reactor for a reaction, enabling a reacted material liquid to flow out from an outlet of the microchannel reactor after the reaction process is finished, and carrying out post-treatment on the reacted material liquid to obtain the 3,4-(1-methyl-indol-3-yl)-1H-pyrrole-2,5-one compound. According to the method disclosed by the invention, the 3,4-(1-methyl-indol-3-yl)-1H-pyrrole-2,5-one is continuously prepared through the microchannel reactor,and the method has the advantages of mild conditions, high reaction speed, high yield, suitability for industrial production, and the like.

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

[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.

TARGETED PEPTIDE CONJUGATES

The present invention relates to the preparation and use of therapeutic compounds for the treatment of diseases at specific subcellular target areas such as specific cellular organelles. In particular, the therapeutic compounds of the invention are specific for modifying enzyme activity within targeted organelles or structures of cells and tissues. Subcellular organelles and structures that may be specifically targeted by compounds of the present invention include lysosomes, autophagasomes, the endoplasmic reticulum, the Golgi complex, peroxisomes, the nucleus, membranes and the mitochondria.

Development of [18F]Maleimide-Based Glycogen Synthase Kinase-3β Ligands for Positron Emission Tomography Imaging

Dysregulation of glycogen synthase kinase-3β (GSK-3β) is implicated in the pathogenesis of neurodegenerative and psychiatric disorders. Thus, development of GSK-3β radiotracers for positron emission tomography (PET) imaging is of paramount importance, because such a noninvasive imaging technique would allow better understanding of the link between the activity of GSK-3β and central nervous system disorders in living organisms, and it would enable early detection of the enzyme’s aberrant activity. Herein, we report the synthesis and biological evaluation of a series of fluorine-substituted maleimide derivatives that are high-affinity GSK-3β inhibitors. Radiosynthesis of a potential GSK-3β tracer [18F]10a is achieved. Preliminary in vivo PET imaging studies in rodents show moderate brain uptake, although no saturable binding was observed in the brain. Further refinement of the lead scaffold to develop potent [18F]-labeled GSK-3 radiotracers for PET imaging of the central nervous system is warranted.

3 - (1, 2, 4 - triazole [4, 3 - a] pyridine - 3 - yl) - 4 - (1H - Indol - 3 - yl) maleimide derivatives and its preparation method and application

The invention provides a 3-(1,2,4-triazolo(4,3-a)pyridine-3-yl)-4-(1H-indole-3-yl)maleimide derivative with a novel structure and a preparation method and application of the derivative. The compound can be used for treating ischemic cerebral apoplexy. The general structural formula of the compound is shown in the specification.

Synthesis and biological evaluation of 3-benzisoxazolyl-4-indolylmaleimides as potent, selective inhibitors of glycogen synthase kinase-3β

A series of novel 3-benzisoxazolyl-4-indolyl-maleimides were synthesized and evaluated for their GSK-3β inhibitory activity. Most compounds exhibited high inhibitory potency towards GSK-3β. Among them, compound 7j with an IC50 value of 0.73 nM was the most promising GSK-3β inhibitor. Preliminary structure-activity relationships were examined and showed that different substituents on the indole ring and N1-position of the indole ring had varying degrees of influence on the GSK-3β inhibitory potency. Compounds 7c, 7f, 7j-l and 7o-q could obviously reduce Aβ-induced Tau hyperphosphorylation by inhibiting GSK-3β in a cell-based functional assay.