944893-74-7

Basic information

• Product Name: 1-ethyl-1H-indole-5-carbaldehyde
• Synonyms: 1-ethyl-1H-indole-5-carbaldehyde;Albb-004946;1-ethyl-1H-indole-5-carbaldehyde(SALTDATA: FREE)
• CAS NO: 944893-74-7
• Molecular Formula: C₁₁H₁₁NO
• Molecular Weight: 173.22
• Mol File: 944893-74-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 327.7°C at 760 mmHg
• Flash Point: 152°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 0.000199mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 1-ethyl-1H-indole-5-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ethyl-1H-indole-5-carbaldehyde(944893-74-7)
• EPA Substance Registry System: 1-ethyl-1H-indole-5-carbaldehyde(944893-74-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 944893-74-7(Hazardous Substances Data)

Usage

General Description

1-ethyl-1H-indole-5-carbaldehyde is an organic compound with the chemical formula C11H11NO. It belongs to the family of indole compounds and is commonly used as an intermediate in the synthesis of various pharmaceuticals and organic materials. 1-ethyl-1H-indole-5-carbaldehyde has a pale yellow color and a sweet floral odor. It is a versatile compound that is utilized in the production of fragrances and flavors, as well as in the development of new drugs and agrochemicals. Its unique chemical structure and properties make it an important building block for the creation of a wide range of compounds with diverse applications.

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 
• 1620139-75-4 4β-(((1-ethylindol-5-yl)methyl)amino)-4'-demethyl-4-desoxypodophyllotoxin 
• 1620139-76-5 4β-(((1-ethylindol-5-yl)methyl)amino)-4-desoxypodophyllotoxin 

Relevant articles and documents

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.

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 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.