51079-10-8

Basic information

• Product Name: (1H-INDOL-3-YL)-OXO-ACETIC ACID ETHYL ESTER
• Synonyms: (1H-INDOL-3-YL)-OXO-ACETIC ACID ETHYL ESTER;ETHYL 3-INDOLEGLYOXYLATE;ethyl indol-3-ylglyoxylate;ETHYL 2-(INDOL-3-YL)-2-OXOACETATE ;α-Oxo-1H-indole-3-acetic acid ethyl ester;ethyl 2-(1H-indol-3-yl)-2-oxoacetate;ETHYL 3-INDOLYLGLYOXYLATE
• CAS NO: 51079-10-8
• Molecular Formula: C₁₂H₁₁NO₃
• Molecular Weight: 217.22
• EINECS: 256-954-5
• Mol File: 51079-10-8.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 391.7 °C at 760 mmHg
• Flash Point: 190.7 °C
• Appearance: /
• Density: 1.278 g/cm³
• Vapor Pressure: 2.41E-06mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (1H-INDOL-3-YL)-OXO-ACETIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (1H-INDOL-3-YL)-OXO-ACETIC ACID ETHYL ESTER(51079-10-8)
• EPA Substance Registry System: (1H-INDOL-3-YL)-OXO-ACETIC ACID ETHYL ESTER(51079-10-8)

Safety Data

• Hazardous Substances Data: 51079-10-8(Hazardous Substances Data)

Usage

Uses

(1H-Indol-3-yl)-oxo-acetic Acid Ethyl Ester is a starting material in synthesizing Indole-3-butyric Acid-d4 (I577802). A labelled Indolebutyric Acid. Used to stimulate root formation of plant clippings. Suitable for plant cell culture tested.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 6141, 1985 DOI: 10.1016/S0040-4039(00)95036-6

InChI:InChI=1/C12H11NO3/c1-2-16-12(15)11(14)9-7-13-10-6-4-3-5-8(9)10/h3-7,13H,2H2,1H3

Upstream product

• 120-72-9 indole 
• 95-92-1 oxalic acid diethyl ester 
• 4755-77-5 Ethyl oxalyl chloride 
• 79-37-8 oxalyl dichloride 
• 64-17-5 ethanol 
• 527-31-1 hexaketocyclohexane 
• 771-51-7 indole-3-acetonitrile 
• 18443-04-4 3-indolylacetic acid ethyl imido ester hydrochloride 
• 2216-92-4 N-phenylglycine ethyl ester 
• 22980-09-2 indolyl-3-glyoxylyl chloride 
• 141-52-6 sodium ethanolate 
• 105632-53-9 tert-butyl 3-(2-ethoxy-2-oxoacetyl)-1H-indole-1-carboxylate 

Downstream Products

• 1477-49-2 3-indolylglyoxylic acid 
• 5055-37-8 2-(1H-indol-3-yl)-2-oxoacetohydrazide 
• 204511-53-5 2-(4-methoxyphenyl)pyrazolo[3,4-c]quinolin-4(5H)-one 
• 109740-09-2 2-phenylpyrazolo[3,4-c]quinolin-4(5H)-one 
• 204511-49-9 2-(3-Fluoro-phenyl)-2,5-dihydro-pyrazolo[3,4-c]quinolin-4-one 
• 204511-59-1 [(2-Fluoro-phenyl)-hydrazono]-(1H-indol-3-yl)-acetic acid ethyl ester 
• 863223-52-3 3-(1H-indol-3-yl)-4-(3,4,5-trimethoxyphenyl)-1H-pyrrole-2,5-dione 
• 125313-57-7 3-(3-indolyl)-4-phenyl-1H-pyrrole-2,5-dione 
• 1415412-32-6 C₂₄H₂₇NO₆ 
• 1415412-42-8 C₂₄H₂₇NO₅ 
• 1415412-43-9 C₂₃H₂₅NO₅ 
• 1415412-44-0 C₂₃H₂₄ClNO₅ 
• 1415412-45-1 C₂₃H₂₄FNO₅ 
• 1415412-46-2 C₂₄H₂₇NO₅ 

Relevant articles and documents

Photoactivatable caged prodrugs of VEGFR-2 kinase inhibitors

In this study, we report on the design, synthesis, photokinetic properties and in vitro evaluation of photoactivatable caged prodrugs for the receptor tyrosine kinase VEGFR-2. Highly potent VEGFR-2 inhibitors 1 and 3 were caged by introduction of a photoremovable protecting group (PPG) to yield the caged prodrugs 4 and 5. As expected, enzymatic and cellular proliferation assays showed dramatically diminished efficacy of caged prodrugs in vitro. Upon ultraviolet (UV) irradiation of the prodrugs original inhibitory activity was completely restored and even distinctly reinforced, as was the case for the prodrug 4. The presented results are a further evidence for caging technique being an interesting approach in the protein kinase field. It could enable spatial and temporal control for the inhibition of VEGFR-2. The described photoactivatable prodrugs might be highly useful as biological probes for studying the VEGFR-2 signal transduction.

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Synthesis and anti-tumor activity of marine alkaloids

Marine alkaloids were divided into five categories from the perspective of anti-tumor activity. The optimization process, chemical synthesis, anti-tumor activity evaluation and structure–activity relationship of various compounds were discussed.

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.

Discovery of Topsentin Alkaloids and Their Derivatives as Novel Antiviral and Anti-phytopathogenic Fungus Agents

Topsentin alkaloids and their derivatives were designed, synthesized, and characterized on the basis of NMR and mass spectroscopy. The antiviral activities against tobacco mosaic virus (TMV) and anti-phytopathogenic fungus activities of these alkaloids were evaluated for the first time. Alkaloids 1c, 1e, 2b, and 2d displayed significantly higher antiviral activities against TMV than Ribavirin, emerging as new lead compounds for anti-TMV research. Further fungicidal activity tests against 14 kinds of phytopathogenic fungi revealed that these alkaloids displayed broad-spectrum fungicidal activities. Topsentin derivative 2d with 4-5 mg/kg EC50 values against Sclerotinia sclerotiorum (Lib.), Rhizoctonia solani (Kuhn), and Botrytis cinerea (Pers.) emerged as a new lead compound for fungicidal research. Current studies provide support for the application of topsentin alkaloids as novel agrochemicals.