52816-02-1

Basic information

• Product Name: 3-(1H-INDOL-3-YL)-3-OXO-PROPIONIC ACID ETHYL ESTER
• Synonyms: CHEMBRDG-BB 5107272;ETHYL 3-(1H-INDOL-3-YL)-3-OXO-PROPIONATE;3-(1H-INDOL-3-YL)-3-OXO-PROPIONIC ACID ETHYL ESTER;ethyl 3-(1H-indol-3-yl)-3-oxopropanoate(SALTDATA: FREE);b-Oxo-1H-indole-3-propanoic acid ethyl ester;ethyl-3-indoloyl-acetate;1H-Indole-3-propanoic acid, beta-oxo-, ethyl ester;ethyl 3-(1H-indol-3-yl)-3-oxopropanoate
• CAS NO: 52816-02-1
• Molecular Formula: C₁₃H₁₃NO₃
• Molecular Weight: 231.25
• Mol File: 52816-02-1.mol

Chemical Properties

• Boiling Point: 391.5°Cat760mmHg
• Flash Point: 190.6°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 2.46E-06mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: 3-(1H-INDOL-3-YL)-3-OXO-PROPIONIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1H-INDOL-3-YL)-3-OXO-PROPIONIC ACID ETHYL ESTER(52816-02-1)
• EPA Substance Registry System: 3-(1H-INDOL-3-YL)-3-OXO-PROPIONIC ACID ETHYL ESTER(52816-02-1)

Safety Data

• Hazardous Substances Data: 52816-02-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
3-(1H-INDOL-3-YL)-3-OXO-PROPIONIC ACID ETHYL ESTER is utilized as a lead compound in pharmaceutical research for its potential to be developed into new drugs. Its unique molecular structure and the presence of an ethyl ester group make it a candidate for the synthesis of medications that could target various biological pathways.
Used in Chemical Reactions:
In the chemical industry, 3-(1H-INDOL-3-YL)-3-OXO-PROPIONIC ACID ETHYL ESTER is used as a reactant in various chemical processes due to its solubility in organic solvents and its reactivity, which allows for the creation of new compounds with potential applications in different fields.
Used in Biological Activity Studies:
3-(1H-INDOL-3-YL)-3-OXO-PROPIONIC ACID ETHYL ESTER is employed in biological research to investigate its potential biological activity. The studies aim to understand how 3-(1H-INDOL-3-YL)-3-OXO-PROPIONIC ACID ETHYL ESTER interacts with biological systems, which could lead to the discovery of its therapeutic uses or mechanisms of action.

InChI:InChI=1/C13H13NO3/c1-2-17-13(16)7-12(15)10-8-14-11-6-4-3-5-9(10)11/h3-6,8,14H,2,7H2,1H3

Upstream product

• 120-72-9 indole 
• 36239-09-5 ethyl chlorocarbonylacetate 
• 18224-54-9 ethyl 3,3-bis(ethylsulfanyl)acrylate 
• 1071-46-1 hydrogen ethyl malonate 
• 76656-82-1 Ethyl α-hydroxyimino-β-keto-β-(3-indolyl)propionate 

Downstream Products

• 1018831-23-6 10H-2-benzyloxymethyl-4-ethoxycarbonyl-5-hydroxy-1,3-dihydropyrrolo[3,4-a]carbazole-1,3-dione 
• 703-80-0 3-acetylindole 

Relevant articles and documents

Visible light-photocatalysed carbazole synthesis: Via a formal (4+2) cycloaddition of indole-derived bromides and alkynes

We successfully developed an unprecedented route to carbazole synthesis through a visible light-photocatalysed formal (4+2) cycloaddition of indole-derived bromides and alkynes. This novel protocol features extremely mild conditions, a broad substrate scope and high reaction efficiency.

Synthesis, in vitro antiproliferative activities, and Chk1 inhibitory properties of indolylpyrazolones and indolylpyridazinedione

The synthesis of 5-indolylpyrazol-3-one, 4-indolylpyrazol-3-one and 4-indolyl-pyridazin-3,6-dione is reported. Their Chk1 inhibitory properties have been evaluated and their in vitro antiproliferative activities toward three tumor cell lines: murine leukemia L1210, human colon carcinoma HT29 and HCT116 have been determined. 4-Indolyl-pyridazin-3,6-dione is inactive against Chk1 and exhibits weak cytotoxicities toward the tumor cell lines tested. The IC50 values toward Chk1 of the two indolylpyrazolones are identical and are in the micromolar range, but the cytotoxicities of 4-indolylpyrazol-3-one are significantly stronger than those of 5-indolylpyrazol-3-one. Since 4-indolylpyrazol-3-one and 5-indolylpyrazol-3-one can present several conformers and tautomeric forms, molecular modelling in the ATP binding site of Chk1 has been carried out to investigate which form could induce the best stabilization in the active site of the enzyme. To get an insight into the kinase selectivity of these compounds, their inhibitory activities toward Src kinase were evaluated.

Structure-Activity Relationship Refinement and Further Assessment of Indole-3-glyoxylamides as a Lead Series against Prion Disease

Structure-activity relationships within the indole-3-glyoxylamide series of antiprion agents have been explored further, resulting in discovery of several new compounds demonstrating excellent activity in a cell line model of prion disease (EC50 10 nM). After examining a range of substituents at the para-position of the N-phenylglyoxylamide moiety, five-membered heterocycles containing at least two heteroatoms were found to be optimal for the antiprion effect. A number of modifications were made to probe the importance of the glyoxylamide substructure, although none were well tolerated. The most potent compounds did, however, prove largely stable towards microsomal metabolism, and the most active library member cured scrapie-infected cells indefinitely on administration of a single treatment. The present results thereby confirm the indole-3-glyoxylamides as a promising lead series for continuing in vitro and in vivo evaluation against prion disease.Making mad cows a myth! The indole-3-glyoxylamide series of antiprion agents has been further optimised, and characteristics contributing to their activity have been identified by computational studies. Varying the glyoxylamide motif or introducing substitution at N-1 gave analogues with lower efficacy.

Heterocyclic substituted pyrazolones

The present invention is directed to novel heterocyclic substituted pyrazolones, including pharmaceutical compositions, diagnostic kits, assay standards or reagents containing the same, and methods of using the same as therapeutics. The invention is also directed to intermediates and processes for making these novel compounds.

ELECTROCHEMICAL SYNTHESIS OF β-KETOTRYPTOPHAN

The reduction of ethyl α-hydroxyimino-β-keto-β-(3-indolyl)propionate was investigated. β-Ketotryptophan and its ethyl ester were obtained.