92855-65-7

Usage

Uses

Used in Organic Synthesis:
7-Benzyloxyindole-3-carbaldehyde is used as a key intermediate in organic synthesis for the production of various chemical compounds. Its unique structure and benzyl group attachment make it a versatile building block for creating a wide range of derivatives.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 7-Benzyloxyindole-3-carbaldehyde is utilized as a starting material or intermediate in the synthesis of various pharmaceuticals. Its potential to form different derivatives allows for the development of new drugs with specific therapeutic properties.
Used in Dye Synthesis:
7-Benzyloxyindole-3-carbaldehyde is also employed as a precursor in the synthesis of dyes, taking advantage of its aromatic and heterocyclic nature to create a variety of colored compounds for different applications.
While the specific applications and biological activities of 7-Benzyloxyindole-3-carbaldehyde may not be widely documented, its role in organic synthesis, pharmaceutical development, and dye production highlights its importance in various chemical industries.

InChI:InChI=1/C16H13NO2/c18-10-13-9-17-16-14(13)7-4-8-15(16)19-11-12-5-2-1-3-6-12/h1-10,17H,11H2

Upstream product

• 20289-27-4 7-benzyloxyindole 
• 68-12-2 N,N-dimethyl-formamide 
• 100-61-8 N-methylaniline 

Downstream Products

• 141834-91-5 N-methyl-N-phenethyl-2-[(7-benzyloxy-3-formyl)indol-1-yl]acetamide 
• 1196967-49-3 (E)-7-(benzyloxy)-3-(2-nitrovinyl)-1H-indole 
• 1346151-20-9 tert-butyl (Z)-4-[(2-{[7-(benzyloxy)-1H-indol-3-yl]methylene}-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate 
• 914348-99-5 tert-butyl 7-(benzyloxy)-3-formyl-1H-indole-1-carboxylate 
• 1415333-55-9 (E)-methyl 3-(7-(benzyloxy)-1H-indole-3-yl)acrylate 
• 141835-01-0 (E)-3-{7-Benzyloxy-1-[(methyl-phenethyl-carbamoyl)-methyl]-1H-indol-3-yl}-acrylic acid ethyl ester 
• 244081-35-4 (R)-3-(2-aminopropyl)-7-benzyloxyindole 
• 307307-35-3 7-benzyloxy-3-(2-nitropropyl)indole 
• 566200-65-5 [2-(3-chloro-phenyl)-2-hydroxy-ethyl]-[2-(7-hydroxy-1H-indol-3-yl)-1-methyl-ethyl]-carbamic acid tert-butyl ester 
• 566200-66-6 3-[(2R)-(7-benzyloxy-1H-indol-3-yl)propyl]-(5R)-(3-chlorophenyl)-1,3-oxazolidin-2-one 

Relevant academic research and scientific papers

N-skatyltryptamines-dual 5-ht6r/d2r ligands with antipsychotic and procognitive potential

A series of N-skatyltryptamines was synthesized and their affinities for serotonin and dopamine receptors were determined. Compounds exhibited activity toward 5-HT1A, 5-HT2A, 5-HT6, and D2 receptors. Substitution patterns resulting in affinity/activity switches were identified and studied using homology modeling. Chosen hits were screened to determine their metabolism, permeability, hepatotoxicity, and CYP inhibition. Several D2 receptor antagonists with additional 5-HT6R antagonist and agonist properties were identified. The former combination resembled known antipsychotic agents, while the latter was particularly interesting due to the fact that it has not been studied before. Selective 5-HT6R antagonists have been shown previously to produce procognitive and promnesic effects in several rodent models. Administration of 5-HT6R agonists was more ambiguous-in naive animals, it did not alter memory or produce slight amnesic effects, while in rodent models of memory impairment, they ameliorated the condition just like antagonists. Using the identified hit compounds 15 and 18, we tried to sort out the difference between ligands exhibiting the D2R antagonist function combined with 5-HT6R agonism, and mixed D2/5-HT6R antagonists in murine models of psychosis.

Synthesis of indolyl-3-acetonitrile derivatives and their inhibitory effects on nitric oxide and PGE2 productions in LPS-induced RAW 264.7 cells

Arvelexin is one of major constituents of Brassica rapa that exerts anti-inflammatory activities. Several indolyl-3-acetonitrile derivatives were synthesized as arvelexin analogs and evaluated for their abilities to inhibit NO and PGE2 productions in LPS-induced RAW 264.7 cells. Of the indolyl-3-acetonitriles synthesized, compound 2k, which possesses a hydroxyl group at C-7 position of the indole ring and an N-methyl substituent, more potently inhibited NO and PGE2 productions and was less cytotoxic than arvelexin on macrophage cells.

INDOLE, INDOLINE DERIVATIVES, COMPOSITIONS COMPRISING THEM AND USES THEREOF

The invention provides indole and indoline derivatives and slats thereof, compositions comprising them and uses thereof for the treatment of diseases and disorders.

NBu4NI-catalyzed C3-formylation of indoles with N-methylaniline

nBu4NI-catalyzed C3-selective formylation of N-H and N-substituted indoles by using N-methylaniline as a formylating reagent was first successfully demonstrated.

Carbamate derivatives of indolines as cholinesterase inhibitors and antioxidants for the treatment of Alzheimer's disease

The cascade of events that occurs in Alzheimer's disease involving oxidative stress and the reduction in cholinergic transmission can be better addressed by multifunctional drugs than cholinesterase inhibitors alone. For this purpose, we prepared a large number of derivatives of indoline-3-propionic acids and esters. They showed scavenging activity against different radicals in solution and significant protection against cytotoxicity in cardiomyocytes and primary cultures of neuronal cells exposed to H2O2 species and serum deprivation at concentrations ranging from 1 nM to 10 μM depending on the compound. For most of the indoline-3-propionic acid derivatives, introduction of N-methyl-N-ethyl or N-methyl-N-(4-methoxyphenyl) carbamate moieties at positions 4, 6, or 7 conferred both acetyl (AChE) and butyryl (BuChE) cholinesterase inhibitory activities at similar concentrations to those that showed antioxidant activity. The most potent AChE inhibitors were 120 (3-(2-aminoethyl) indolin-4-yl ethyl(methyl)carbamate dihydrochloride) and 94 (3-(3-methoxy-3-oxopropyl)-4-(((4-methoxyphenyl)(methyl) carbamoyl)oxy)indolin- 1-ium hydrochloride) with IC50s of 0.4 and 1.2 μM, respectively.

Discovery of a novel and potent human and rat β3-adrenergic receptor agonist, [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl] -1H-indol-7-yloxy]acetic acid

In search for potent and selective β3-adrenergic receptor (β3-AR) agonists as potential drugs for the treatment of type II diabetes and obesity, a novel series of 1-(3-chlorophenyl)-2-aminoethanol derivatives were prepared and evaluated for their biological activity at human β1-, β2-, and β3-ARs and rat β3-AR expressed in Chinese hamster ovary (CHO) cells. Replacement of the right-hand side (RHS, benzene ring) in the 'first generation' β3-AR agonists BRL 37344 and CL 316243 with a 1H-indole ring gave compound 31 with unique pharmacological properties among β3-AR agonists. Initial in vitro assays showed that 31 possesses modest rat and human β3-ARs agonistic activity. Introduction of various substituent into the indole nucleus of 31 afforded a number of compounds with good β3-ARs agonistic activity. In particular, 90 having a carboxylic acid functionality at the 7-position of the indole nucleus showed the most potent human β3-AR agonistic activity. Finally, optical resolution of 90 led to the identification of the most promising compound, [3-[(2R)-[[(2R)-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1H- indol-7-yloxy]acetic acid (96, AJ-9677). This compound exhibited potent human β3-AR agonistic activity (EC50 = 0.062 nM, IA = 116%) with 210- and 103-fold selectivity over human β2-AR and β1-AR, respectively. Compound 96 also exhibited potent rat β3-AR agonistic activity (EC50 = 0.016 nM, IA = 110%). Moreover, repeated oral administration of 96 inhibited body weight gain and significantly decreased glucose, insulin, free fatty acid, and triglyceride concentrations in plasma in KK-Ay/Ta mice. On the basis of this pharmacological profile, 96 entered clinical development as a drug for the treatment of type II diabetes and obesity.

Structure-activity relationship study of novel necroptosis inhibitors

Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-α. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration.

Novel and potent human and rat β3-adrenergic receptor agonists containing substituted 3-indolylalkylamines

A novel series of 2-(3-indolyl)alkylamino-1-(3-chlorophenyl)ethanols was prepared and evaluated for in vitro ability to stimulate cAMP production in Chinese hamster ovary cells expressing cloned human β3-AR. The optically active 30a was found to be the most potent and selective human β3-AR agonist in this series with an EC50 value of 0.062 nM. In addition, 30a selectivity for human β3-AR was 210-fold and 103-fold that for human β2-AR and β1-AR, respectively. Furthermore, 30a showed potent agonistic activity at rat β3-AR.

A scalable synthesis of (R)-3-(2-aminopropyl)-7-benzyloxyindole via resolution

(±)-3-(2-Aminopropyl)-7-benzyloxyindole 1, assembled from 7-benzyloxyindole 3 in 59% overall yield, is resolved with O,O′-di-p-toluoyl L-(2R,3R)-tartaric acid 7 into (R)-1, a key intermediate of AJ-9677 2 (selective adrenaline β3-agonist) in 99