1074-86-8

Usage

Uses

Indole-4-carboxaldehyde is used in multiple applications across different industries, primarily as a reactant in various chemical reactions and pharmaceutical synthesis.
Used in Pharmaceutical Synthesis:
Indole-4-carboxaldehyde is used as a synthetic intermediate for the preparation of antitumor agents, contributing to the development of cancer treatments.
Used in Biginelli Reaction:
In the field of organic chemistry, Indole-4-carboxaldehyde is used as a reactant in the Biginelli reaction, which is a multicomponent reaction for the synthesis of dihydropyrimidinones.
Used in the Synthesis of Aurora Kinase A Inhibitors:
Indole-4-carboxaldehyde is utilized in the synthesis of aurora kinase A inhibitors, which are important in the development of targeted cancer therapies.
Used in Intramolecular Friedel-Crafts Acylation:
The compound is also used in intramolecular Friedel-Crafts acylation, a chemical reaction that involves the formation of a cyclic compound through the acylation of an aromatic ring.
Used in the Preparation of Inhibitors of Cell Division in E. Coli:
Indole-4-carboxaldehyde is employed in the preparation of inhibitors that prevent cell division in E. coli, which can have implications in the study of bacterial growth and antibiotic development.
Used in the Synthesis of Hantzsch Pyridine-Containing Schiff Bases:
The compound is also used in the synthesis of Hantzsch pyridine-containing Schiff bases, which are important in the field of coordination chemistry and have potential applications in various areas, including catalysis and medicinal chemistry.

Synthesis Reference(s)

The Journal of Organic Chemistry, 46, p. 1752, 1981 DOI: 10.1021/jo00321a053Tetrahedron, 39, p. 3695, 1983 DOI: 10.1016/S0040-4020(01)88608-7

InChI:InChI=1/C9H7NO/c11-6-7-2-1-3-9-8(7)4-5-10-9/h1-6,10H

Upstream product

• 52488-36-5 4-bromo-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 16136-52-0 4-cyanoindole 
• 42792-95-0 2-methyl-5-nitroisoquinolin-2-ium iodide 
• 35577-89-0 1-[(4-methylbenzene)sulfonyl]-4,5,6,7-tetrahydro-1H-indol-4-one 
• 39830-66-5 methyl 1H-indole-4-carboxylate 
• 19384-71-5 5-amino-2-methylisoquinolinium iodide 
• 79681-04-2 1-[(4-methyl-phenyl)-sulfonyl]-1H-indol-4-carboxaldehyde 
• 127693-25-8 2-(2-methyl-3-nitrophenyl)-1,3-dioxolane 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 3468-22-2 (1H-indol-4-yl)-N-methylmethanamine 
• 88059-19-2 trans-6-cyano-β-dimethylamino-2-nitrostyrene 
• 76499-46-2 3-nitro-2-<2-(1-pyrrolidinyl)ethenyl>benzaldehyde dimethyl acetal 
• 112447-73-1 1-Triisopropylsilanyl-1H-indole-4-carbaldehyde 

Downstream Products

• 133994-99-7 1-methyl-1H-indol-4-carboxaldehyde 
• 894852-86-9 1-ethyl-1H-indole-4-carbaldehyde 
• 1232221-52-1 N-(1H-indol-4-yl-methylidene)-N'-(7-morpholin-4-yl-2-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)-hydrazine 
• 1403763-02-9 2-(1H-indol-4-yl)-2-((2-((4-methoxyphenethyl)amino)-2-oxoethyl)amino)-N-phenethylacetamide 

Relevant academic research and scientific papers

Synthesis of indole-4-carboxaldehydes and 4-Acetylindole from N-alkyl-5-aminoisoquinolinium salts

N-Alkyl-5-aminoisoquinolinium salts (8a-d) are converted into indole-4-carboxaldehydes (1a-c) on heating in a two phase alkyl acetate-water system containing an excess of a 2:1 sodium bisulfite-sodium sulfite mixture, 4-Acetylindole 1e is prepared in the same way from 1-methyl-2-cyanomethylisoquinolinium bromide 8f.

Palladium-catalyzed external-CO-free reductive carbonylation of aryl sulfonates

Pd-catalyzed reductive carbonylation of aryl sulfonates using N-formylsaccharin as a carbon monoxide (CO) surrogate was developed. This external-CO-free carbonylation provides a safe and practical access to aldehydes from phenol derivatives. The reaction has a broad substrate scope, rendering it an attractive method for synthesizing aldehydes.

Dopamine receptor ligands. Part 18: Modification of the structural skeleton of indolobenzazecine-type dopamine receptor antagonists

On the basis of the D1/5-selective dopamine antagonist LE 300 (1), an indolo[3,2-f]benzazecine derivative, we changed the annulation pattern of the heterocycles. The target compounds represent novel heterocyclic ring systems. The most constrained indolo[4,3a,3-ef]benzazecine 2 was inactive, but the indolo[4,3a,3-fg]benzazacycloundecene 3 showed antagonistic properties (functional Ca2+ assay) with nanomolar affinities (radioligand binding) for all dopamine receptor subtypes, whereas the indolo[2,3-f] benzazecine 4 displayed a selectivity profile similar to 3 but with decreased affinities.

THERAPEUTIC AGENTS, AND METHODS OF MAKING AND USING THE SAME

In part, the present invention is directed to antibacterial compounds

Novel 4-phenyl substituted tetrahydroisoquinolines and therapeutic use thereof

The present invention relates to a method of treating disorders including cognition impairment, generalized anxiety disorder, acute stress disorder, social phobia, simple phobias, pre-menstrual dysphoric disorder, social anxiety disorder, major depressive

Glucagon antagonists/inverse agonists

Non-peptide compounds comprising a central hydrazide motif and methods for the synthesis thereof are disclosed. The compounds act to antagonize the action of the glucagon peptide hormone.

Optimization of alkylidene hydrazide based human glucagon receptor antagonists. Discovery of the highly potent and orally available 3-cyano-4-hydroxybenzoic acid [1-(2,3,5,6-tetramethylbenzyl)-1h-indol-4ylmethylene]hydrazide

Highly potent human glucagon receptor (hGluR) antagonists have been prepared employing both medicinal chemistry and targeted libraries based on modification of the core (proximal) dimethoxyphenyl group, the benzyl ether linkage, as well as the (distal) benzylic aryl group of the lead 2, 3-cyano-4-hydroxybenzoic acid (3,5-dimethoxy-4-isopropylbenzyloxybenzylidene)hydrazide. Electron-rich proximal aryl moieties such as mono- and dimethoxy benzenes, naphthalenes, and indoles were found to be active. The SAR was found to be quite insensitive regarding the linkage to the distal aryl group, since long and short as well as polar and apolar linkers gave highly potent compounds. The presence of a distal aryl group was not crucial for obtaining high binding affinity to the hGluR. In many cases, however, the affinity could be further optimized with substituted distal aryl groups. Representative compounds have been tested for in vitro metabolism, and structure - metabolism relationships are described. These efforts lead to the discovery of 74, NNC 25-2504, 3-cyano-4-hydroxybenzoic acid [1-(2,3,5,6tetramethylbenzyl)-1H-indol-4-ylmethylene]hydrazide, with low in vitro metabolic turnover. 74 was a highly potent noncompetitive antagonist of the human glucagon receptor (IC50 = 2.3 nM, KB = 760 pM) and of the isolated rat receptor (IC50 = 430 pM, KB = 380 pM). Glucagonstimulated glucose production from isolated primary rat hepatocytes was inhibited competitively by 74 (Ki = 14 nM). This compound was orally available in dogs (Fpo = 15%) and was active in a glucagon-challenged rat model of hyperglucagonemia and hyperglycemia.

Novel 4-phenyl substituted tetrahydroiso quinolines therapeutic use thereof

Compounds are provided that, by way of their selective neurotransmitter binding useful for the treatment of various neurological and psychological disorders, e.g., ADHD. Such compounds are 4-phenyl substituted tetrahydroisoquinolines having the Formula IA, IB, IIA, IIB, IIIA or IIIC as set forth herein.

Thiazolidinedione derivatives, method for preparing the derivatives and pharmaceutical compositions containing same

A thiazolidinedione derivative represented by the following general formula (I): STR1 ?wherein the dotted line represents a single bond or a double bond, the thiazolidinedione ring residue is linked to either of 2-, 3-, 4-, 5- and 6-positions on the indole ring and R represents a group selected from the group consisting of hydrogen atom and alkyl, alkenyl, alkynyl, phenyl, aralkyl, heterocycloalkyl, arylsulfonyl and arylaminocarbonyl groups! or a pharmaceutically acceptable salt thereof exhibits excellent effects of reducing the blood sugar level and of reducing the lipid concentration in blood and is accordingly useful as a therapeutic agent for treating diabates mellitus. These derivatives and pharmaceutically acceptable salt thereof are almost free of any side effect.

Azepinoindole derivatives with high affinity for brain dopamine and serotonin receptors

We synthesized 20 and 21 as conformationally constrained analogues of the dopamine receptor antagonist SKF-83742, as well as analogues 6-9, 16, and 18-22. Although 20 and 21 were inactive, 7, 9, and 19 showed strong binding to D-1, D-2, S-2, and α-1 receptors, as well as antipsychotic activity in vivo.