25055-54-3

Basic information

• Product Name: ethyl 2-(1-methylindol-3-yl)-2-oxo-acetate
• Synonyms: ethyl 2-(1-methylindol-3-yl)-2-oxo-acetate
• CAS NO: 25055-54-3
• Molecular Formula: C₁₃H₁₃NO₃
• Molecular Weight: 231.25
• Mol File: 25055-54-3.mol

Chemical Properties

• Boiling Point: 381.2°Cat760mmHg
• Flash Point: 184.3°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 5.18E-06mmHg at 25°C
• Refractive Index: 1.57
• CAS DataBase Reference: ethyl 2-(1-methylindol-3-yl)-2-oxo-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-(1-methylindol-3-yl)-2-oxo-acetate(25055-54-3)
• EPA Substance Registry System: ethyl 2-(1-methylindol-3-yl)-2-oxo-acetate(25055-54-3)

Safety Data

• Hazardous Substances Data: 25055-54-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H13NO3/c1-3-17-13(16)12(15)10-8-14(2)11-7-5-4-6-9(10)11/h4-8H,3H2,1-2H3

Upstream product

• 120-72-9 indole 
• 1415810-65-9 ethyl 2-(1-methyl-1H-indol-3-yl)-2-(p-tolylamino)acetate 
• 51584-17-9 1-methyl-1H-indole-3-acetonitrile 
• 603-76-9 1-methylindole 
• 4755-77-5 Ethyl oxalyl chloride 

Downstream Products

• 125313-97-5 3-(1-methyl-3-indolyl)-4-phenyl-1H-pyrrole-2,5-dione 
• 125313-98-6 3-(4-methoxyphenyl)-4-(1-methyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione 

Relevant articles and documents

Electrochemically Enabled C3-Formylation and -Acylation of Indoles with Aldehydes

Reported herein is an effective strategy for oxidative cross-coupling of indoles with various aldehydes. The strategy is based on a two-step transformation via a well-known Mannich-type reaction and a C-N bond cleavage for carbonyl introduction. The key step - the C-N bond cleavage of the Mannich product - was enabled by electrochemistry. This strategy (with over 40 examples) ensures excellent functional-group tolerance as well as late-stage functionalization of pharmaceutical molecules.

Copper(II)-Catalyzed Benzylic C(sp3)-H Aerobic Oxidation of (Hetero)Aryl Acetimidates: Synthesis of Aryl-α-ketoesters

A straightforward method is developed in this paper for the synthesis of α-ketoesters through copper-catalyzed aerobic oxidation of (hetero)aryl acetimidates using molecular oxygen as a sustainable oxidant. The reaction represents the first example of the direct synthesis of aryl-α-ketoesters from arylacetimidates through the aerobic oxidation of a benzylic C(sp3)-H (CO) bond in moderate to good yield. This transformation occurs under mild reaction conditions with a wide range of substrates and utilizes a readily available oxidant and catalyst. The synthetic utility of this transformation is demonstrated through scaled-up synthesis. A plausible reaction mechanism is also proposed.

From a natural product lead to the identification of potent and selective benzofuran-3-yl-(indol-3-yl)maleimides as glycogen synthase kinase 3βinhibitors that suppress proliferation and survival of pancreatic cancer cells

Recent studies have demonstrated that glycogen synthase kinase 3β (GSK-3β) is overexpressed in human colon and pancreatic carcinomas, contributing to cancer cell proliferation and survival. Here, we report the design, synthesis, and biological evaluation of benzofuran-3-yl-(indol-3-yl) maleimides, potent GSK-3β inhibitors. Some of these compounds show picomolar inhibitory activity toward GSK-3β and an enhanced selectivity against cyclin-dependent kinase 2 (CDK-2). Selected GSK-3β inhibitors were tested in the pancreatic cancer cell lines MiaPaCa-2, BXPC-3, and HupT3. We determined that some of these compounds, namely compounds 5, 6, 11, 20, and 26, demonstrate antiproliferative activity against some or all of the pancreatic cancer cells at low micromolar to nanomolar concentrations. We found that the treatment of pancreatic cancer cells with GSK-3β inhibitors 5 and 26 resulted in suppression of GSK-3β activity and a distinct decrease of the X-linked inhibitor of apoptosis (XIAP) expression, leading to significant apoptosis. The present data suggest a possible role for GSK-3β inhibitors in cancer therapy, in addition to their more prominent applications in CNS disorders.

Structure-based design leads to the identification of lithium mimetics that block mania-like effects in rodents. Possible new GSK-3β therapies for bipolar disorders

More than two million American adults, or approximately one percent of the population 18 years or older, suffer from bipolar disorder. Current treatments include the so-called "mood stabilizers," lithium and valproic acid. Both are relatively dated drugs that are only partially effective and produce various undesirable side effects including weight gain. Based upon continued efforts to understand the molecular target for lithium, it now appears that specific inhibitors of the enzyme glycogen synthase kinase-3β (GSK-3β) may mimic the therapeutic action of mood stabilizers and might therefore allow for the design of improved drugs for treating patients with bipolar disorder as well as certain neurodegenerative disorders. Furthermore, the pro-apoptotic properties of the GSK-3 enzyme suggest the possible use of such inhibitors as neuroprotective agents. In fact, neuroprotection may contribute to the treatment of mood disorders. The present chemistry, modeling, and biology efforts have identified 3-benzofuranyl-4-indolylmaleimides as potent and relatively selective GSK-3β inhibitors. The best ligand in this series (having a Ki value of 4.6 nM against GSK-3β) was studied in a novel mouse model of mania that has recently been validated with several clinically effective mood stabilizers. This study presents the first demonstration of the efficacy of a GSK-3β inhibitor in this mouse model of mania. Selective brain penetrable GSK-3 ligands like those described herein become valuable research tools in better defining the role of this multifaceted kinase in both physiological and pathophysiological events.