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
• Article Data: 4

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.

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.