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Usage

Uses

Used in Pharmaceutical Industry:
1-ethyl-1H-indole-5-carbaldehyde is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Fragrance and Flavor Industry:
1-ethyl-1H-indole-5-carbaldehyde is used as a component in the production of fragrances and flavors due to its sweet floral odor, enhancing the sensory qualities of various products.
Used in Agrochemical Development:
1-ethyl-1H-indole-5-carbaldehyde is utilized in the development of new agrochemicals, where its unique properties can contribute to the creation of effective and innovative products for agricultural applications.
Used in Organic Material Synthesis:
1-ethyl-1H-indole-5-carbaldehyde is used as a building block in the synthesis of organic materials, allowing for the creation of a wide range of compounds with different properties and uses.

InChI:InChI=1/C11H11NO/c1-2-12-6-5-10-7-9(8-13)3-4-11(10)12/h3-8H,2H2,1H3

Upstream product

• 1196-69-6 1H-indole-5-carboxaldehyde 
• 75-03-6 ethyl iodide 
• 74-96-4 ethyl bromide 

Downstream Products

• 1354970-03-8 1-ethyl-3,5-bis[(E)-2-phenylethenyl]-1H-indole 
• 1354970-05-0 1-ethyl-3,5-bis[(E)-2-(3-methoxyphenyl)ethenyl]-1H-indole 
• 1354970-06-1 1-ethyl-3,5-bis[(E)-2-(3-fluorophenyl)ethenyl]-1H-indole 
• 1620139-76-5 4β-(((1-ethylindol-5-yl)methyl)amino)-4-desoxypodophyllotoxin 
• 1620139-75-4 4β-(((1-ethylindol-5-yl)methyl)amino)-4'-demethyl-4-desoxypodophyllotoxin 

Relevant academic research and scientific papers

COMPOUNDS AND COMPOSITIONS FOR THE TREATMENT OF TUMORS

The present invention relates to compounds of Formula (Ia) or pharmaceutically acceptable salts, hydrates, solvates, clathrates, polymorphs, stereoisomers thereof. It further discloses a pharmaceutical composition comprising compounds of Formula (Ia) and the use of compounds of Formula (Ib), in particular for the use in the treatment of diseases or disorders wherein disrupting Rad51-BRCA2 interaction is beneficial.

Synthetic Lethality in Pancreatic Cancer: Discovery of a New RAD51-BRCA2 Small Molecule Disruptor That Inhibits Homologous Recombination and Synergizes with Olaparib

Synthetic lethality is an innovative framework for discovering novel anticancer drug candidates. One example is the use of PARP inhibitors (PARPi) in oncology patients with BRCA mutations. Here, we exploit a new paradigm based on the possibility of triggering synthetic lethality using only small organic molecules (dubbed "fully small-molecule-induced synthetic lethality"). We exploited this paradigm to target pancreatic cancer, one of the major unmet needs in oncology. We discovered a dihydroquinolone pyrazoline-based molecule (35d) that disrupts the RAD51-BRCA2 protein-protein interaction, thus mimicking the effect of BRCA2 mutation. 35d inhibits the homologous recombination in a human pancreatic adenocarcinoma cell line. In addition, it synergizes with olaparib (a PARPi) to trigger synthetic lethality. This strategy aims to widen the use of PARPi in BRCA-competent and olaparib-resistant cancers, making fully small-molecule-induced synthetic lethality an innovative approach toward unmet oncological needs.

Substitution at the indole 3 position yields highly potent indolecombretastatins against human tumor cells

Resistance to combretastatin A-4 is mediated by metabolic modification of the phenolic hydroxyl and ether groups of the 3-hydroxy-4-methoxyphenyl (B ring). Replacement of the B ring of combretastatin A-4 by a N-methyl-5-indolyl reduces tubulin polymerization inhibition (TPI) and cytotoxicity against human cancer cell lines but cyano, methoxycarbonyl, formyl, and hydroxyiminomethyl substitutions at the indole 3-position restores potent TPI and cytotoxicity against sensitive human cancer cell lines. These highly potent substituted derivatives displayed low nanomolar cytotoxicity against several human cancer cell lines due to tubulin inhibition, as shown by cell cycle analysis, confocal microscopy, and tubulin polymerization inhibitory activity studies, and promoted cell killing mediated by caspase-3 activation. Binding at the colchicine site was suggested by molecular modeling studies. Substituted combretastatins displayed higher potencies than the isomeric isocombretastatins and the highest potencies were achieved for the hydroxyiminomethyl (21) and cyano (23) groups, with TPI values in the submicromolar range and cytotoxicities in the nanomolar and subnanomolar range. Dose-response and time-course studies showed that drug concentrations as low as 1 nM (23) or 10 nM (21) led to a complete G2/M cell cycle arrest after 15 h treatment followed by a high apoptosis-like cell response after 48–72 h treatment. The P-glycoprotein antagonist verapamil increased 21 and 23 cytotoxicity to IC50 values of 10?10 M, and highly potentiated the cytotoxic activity in 100-fold of the CHO derivative (17), in A-549 human non-small cell lung cancer cells. The cyano substituted indolecombretastatin 23 is by itself highly potent against rather resistant HT-29 and A-549 cell lines. A 3,4,5-trimethoxyphenyl ring always afforded more potent derivatives than a 2,3,4-trimethoxyphenyl ring.

Synthesis of podophyllotoxin derivatives as potential antitumor agents

A series of novel podophyllotoxin derivatives was synthesized by coupling 4β-amino-4′-demethyl-4-desoxypodophyllotoxin (3a) or 4β-amino-4-desoxypodophyllotoxin (3b) with N-substituted 5-formylindole (2a-h). Their structures were identied by spectroscopic techniques. These novel derivatives were evaluated for cytotoxicity in vitro against HepG2 and HeLa cell lines. Compared with etoposide, most of the compounds showed more potent cytotoxicities against two tumor cell lines. Judging from the IC50 values, compound 5n is a promising agent, which is about 15 and 5 times more toxic than etoposide against HepG2 and HeLa cell lines, respectively.

Synthesis of 3,5-diaryl substituted indole derivatives and its selective iodide ion chemosensing

In this contribution, we have synthesized series of 1-ethyl-3,5-bis[2- (aryl)ethenyl]-1H-indole based derivatives with different functional groups using Wadsworth-Emmons coupling. The sensing ability of the receptors has been studied for halides like tetrabutylammonium fluoride, chloride, bromide, iodide and bisulphate by UV-vis spectroscopy methods. In THF solution, compound A-E exhibits excellent selectivity with iodide ions over the other ions like tetrabutylammonium bromide (TBABr), tetrabutylammonium chloride (TBACl), tetrabutylammonium fluoride (TBAF) and tetrabutylammonium bisulphate (TBAHSO4). The indole cores were observed effectively and selectively recognized biologically important iodide was reported. Significant absorption change was observed only for tetrabutylammonium iodide and no change with other anions. The absorption spectra indicated the formation of complex between host and guest is in 1:1 stoichiometric ratio. The association constants of A-E for iodide ions were found to be 3.2 × 104 M-1, 3.9 × 104 M-1, 4.2 × 103 M -1, 2.9 × 103 M-1 and 2.14 × 103 M-1, respectively.