51079-10-8

Usage

Uses

Used in Plant Growth Regulation:
(1H-INDOL-3-YL)-OXO-ACETIC ACID ETHYL ESTER is used as a growth regulator in the agricultural industry for its ability to stimulate root formation in plant clippings. This application is particularly beneficial for promoting the growth and development of plants, leading to healthier and more robust crops.
Used in Plant Cell Culture Testing:
In the field of plant cell culture, (1H-INDOL-3-YL)-OXO-ACETIC ACID ETHYL ESTER is utilized as a testing agent to evaluate its effectiveness in promoting root formation and overall plant growth. This allows researchers and scientists to study its potential applications and optimize its use in various plant growth scenarios.

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

• 22980-09-2 indolyl-3-glyoxylyl chloride 
• 64-17-5 ethanol 
• 4755-77-5 Ethyl oxalyl chloride 
• 95-92-1 oxalic acid diethyl ester 
• 18443-04-4 3-indolylacetic acid ethyl imido ester hydrochloride 
• 771-51-7 indole-3-acetonitrile 
• 120-72-9 indole 
• 527-31-1 hexaketocyclohexane 
• 79-37-8 oxalyl dichloride 
• 2216-92-4 N-phenylglycine ethyl ester 
• 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 
• 863223-52-3 3-(1H-indol-3-yl)-4-(3,4,5-trimethoxyphenyl)-1H-pyrrole-2,5-dione 
• 950822-49-8 C₁₇H₁₃N₃O₂ 
• 73790-03-1 ethyl 1-(4-chlorobenzoyl)-α,α-difluoro-3-indoleacetate 
• 1415412-32-6 C₂₄H₂₇NO₆ 
• 1415412-42-8 C₂₄H₂₇NO₅ 
• 1415412-43-9 C₂₃H₂₅NO₅ 
• 1415412-44-0 C₂₃H₂₄ClNO₅ 
• 1415412-45-1 C₂₃H₂₄FNO₅ 
• 1415412-46-2 C₂₄H₂₇NO₅ 
• 1415412-47-3 C₂₄H₂₇NO₆ 
• 1415412-48-4 C₂₃H₂₄ClNO₅ 
• 1415412-49-5 C₂₃H₂₄FNO₅ 

Relevant academic research and scientific papers

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.

THERMOLYTIC REMOVAL OF t-BUTYLOXYCARBONYL (BOC) PROTECTING GROUP ON INDOLES AND PYRROLES

The t-Butyloxycarbonyl (BOC) group on indoles and pyrroles can be removed cleanly and in high yield by simple thermolysis: no acid, no base, no solvent is required.

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.

Exploring of indole derivatives for ESIPT emission: A new ESIPT-based fluorescence skeleton and TD-DFT calculations

Appropriate synthesis methods gave six different indole derivatives substituted at the C-2 or C-3 position. ESIPT emission capacities of these derivatives were investigated. It was concluded that the indole derivative containing the 1,2-dicarbonyl group at the C-2 position has ESIPT emission. Although adding water to the DMSO solution of the ESIPT-based molecule (9:1) resulted in ESIPT quenching, steady-state measurements in MeOH did not occur ESIPT quenching. TD-DFT calculation for uncovering the ESIPT mechanism emerged that the ESIPT mechanism occurred as a barrierless process. The X-ray analysis and DFT conformational analysis revealed that NH and CO groups involving proton transfer mechanisms are in the cis position. A mono-exponential decay was observed in DMSO and MeOH solutions, in which lifetimes were measured as 6.1 and 5.5 ns, respectively. pH studies revealed that acidic and basic solutions of molecule 7 did not influence ESIPT emission.

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.

Synthesis of 3-acylated indoles through iron-catalyzed oxidative coupling of indoles with α-amino carbonyl compounds

A novel iron-catalyzed oxidative coupling of indoles with α-amino carbonyl compounds has been developed. The transformation provides an attractive approach to the synthesis of 3-acylindoles, with the advantages of easily available starting materials and high functional group tolerance. Furthermore, control experiments imply that a radical process maybe involved in this reaction.

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.

Enantioselective Model Synthesis and Progress toward the Putative Structure of Yuremamine

An enantioselective model synthesis of the 2,3-dihydro-1H-pyrrolo[1,2-a]indole core of the putative structure of yuremamine is reported in 39% overall yield and 96% ee over five steps. The model synthesis leverages enantioselective, rhodium-catalyzed hydroacylation of an N-vinylindole-2-carboxaldehyde as the key step in the installation of the stereochemical triad. An enantioselective synthesis of a densely functionalized dihydropyrroloindolone that maps onto the putative structure of yuremamine is demonstrated in 26% yield and 97% ee over eight steps.

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.

Determinants of activity at human toll-like receptors 7 and 8: Quantitative Structure-Activity Relationship (QSAR) of diverse heterocyclic scaffolds

Toll-like receptor (TLR) 7 and 8 agonists are potential vaccine adjuvants, since they directly activate APCs and enhance Th1-driven immune responses. Previous SAR investigations in several scaffolds of small molecule TLR7/8 activators pointed to the strict dependence of the selectivity for TLR7 vis-à-vis TLR8 on the electronic configurations of the heterocyclic systems, which we sought to examine quantitatively with the goal of developing heuristics to define structural requisites governing activity at TLR7 and/or TLR8. We undertook a scaffold-hopping approach, entailing the syntheses and biological evaluations of 13 different chemotypes. Crystal structures of TLR8 in complex with the two most active compounds confirmed important binding interactions playing a key role in ligand occupancy and biological activity. Density functional theory based quantum chemical calculations on these compounds followed by linear discriminant analyses permitted the classification of inactive, TLR8-active, and TLR7/8 dual-active compounds, confirming the critical role of partial charges in determining biological activity.