50656-47-8

Upstream product

• 3189-22-8 7-methoxy-1H-indole 
• 79-37-8 oxalyl dichloride 
• 53055-05-3 3-methoxy 2-nitrobenzaldehyde 
• 16990-40-2 1-(2-nitro-3-methoxyphenyl)-2-nitroethene 
• 350821-42-0 1-(3-methoxy-2-nitrophenyl)-2-nitroethanol 

Downstream Products

• 313334-83-7 C₂₂H₂₁N₃O₄ 
• 2436-04-6 2-(7-methoxy-indol-3-yl)-ethylamine 
• 1347685-44-2 1-(4-benzylpiperidin-1-yl)-2-(7-hydroxy-1H-indol-3-yl)ethane-1,2-dione 
• 1347685-29-3 1-(4-benzylpiperidin-1-yl)-2-(7-methoxy-1H-indol-3-yl)ethane-1,2-dione 
• 906065-88-1 3-(2-benzyl-8-methoxy-2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)-propionic acid 2,2,2-trifluoro-ethyl ester 
• 906065-89-2 3-benzyl-8-methoxy-1,2,3,3a,4,5-hexahydro-indolo[3,2,1-de][1,5]naphthyridin-6-one 
• 906065-87-0 7-methoxy-N_b-benzyltryptamine 
• 850008-37-6 7-methoxyindoleacetic acid 
• 1067137-41-0 C₂₄H₂₈O₄N₂ 
• 906065-86-9 7-methoxy-N_b-benzyl-3-indoleglyoxylamide 

Relevant academic research and scientific papers

Alpha-ethyltryptamines as dual dopamine-serotonin releasers

The dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporter releasing activity and serotonin-2A (5-HT2A) receptor agonist activity of a series of substituted tryptamines are reported. Three compounds, 7b, (+)-7d and 7f, were found to be potent dual DA/5-HT releasers and were >10-fold less potent as NE releasers. Additionally, these compounds had different activity profiles at the 5-HT2Areceptor. The unique combination of dual DA/5-HT releasing activity and 5-HT2Areceptor activity suggests that these compounds could represent a new class of neurotransmitter releasers with therapeutic potential.

Synthesis and biological characterization of 3-substituted-1h-indoles as ligands of GluN2B-containing N-methyl-D-aspartate receptors

As an extension of our studies, novel indole derivatives were rationally designed and synthesized as ligands targeted to GluN2B/NMDA receptors. The 2-(4-benzylpiperidin-1-yl)-1-(6-hydroxy-1H-indol-3-yl)ethanone (4i) and 1-(4-benzylpiperidin-1-yl)-2-(6-hydroxy-1H-indol-3-yl)ethane-1,2-dione (6i) showed high binding affinity in [3H]ifenprodil displacement assay. By computational studies, we suggested the hypothetical interactions playing a significant role during the binding process. However, in functional and in vivo studies the most potent compound 4i did not show any activity whereas it displayed relevant affinity toward the σ2 receptor.

Inhibitors of HIV-1 attachment. Part 2: An initial survey of indole substitution patterns

The effects of introducing simple halogen, alkyl, and alkoxy substituents to the 4, 5, 6 and 7 positions of 1-(4-benzoylpiperazin-1-yl)-2-(1H-indol-3-yl)ethane-1,2-dione, an inhibitor of the interaction between HIV gp120 and host cell CD4 receptors, on activity in an HIV entry assay was examined. Small substituents at C-4 generally resulted in increased potency whilst substitution at C-7 was readily tolerated and uniformly produced more potent HIV entry inhibitors. Substituents deployed at C-6 and, particularly, C-5 generally produced a modest to marked weakening of potency compared to the prototype. Small alkyl substituents at N-1 exerted minimal effect on activity whilst increasing the size of the alkyl moiety led to progressively reduced inhibitory properties. These studies establish a basic understanding of the indole element of the HIV attachment inhibitor pharmacophore.

Three oxidative metabolites of indole-3-acetic acid from Arabidopsis thaliana

Three metabolites of indole-3-acetic acid (IAA), N-(6-hydroxyindol-3-ylacetyl)-phenylalanine (6-OH-IAA-Phe), N-(6-hydroxyindol-3-ylacetyl)-valine (6-OH-IAA-Val), and 1-O-(2-oxoindol-3-ylacetyl)-β-d-glucopyranose (OxIAA-Glc), were found by a liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS)-based search for oxidative IAA metabolites during the vegetative growth of Arabidopsis. Their structures were confirmed by making a comparison of chromatographic characteristics and mass spectra between naturally occurring compounds and synthetic standards. An incorporation study using deuterium-labeled compounds showed that 6-OH-IAA-Phe and 6-OH-IAA-Val were biosynthesized from IAA-Phe and IAA-Val, respectively, which strongly suggested the formation of these amino acid conjugates of IAA in plants. Both 6-OH-IAA-Phe and 6-OH-IAA-Val were inactive as auxins, as indicated by no significant root growth inhibition in Arabidopsis. Quantitative analysis demonstrated that OxIAA-Glc was present in the largest amount among the metabolites of IAA in Arabidopsis, suggesting that the conversion into OxIAA-Glc represents the main metabolic process regarding IAA in Arabidopsis.

Studies of new indole alkaloid coupling methods for the synthesis of haplophytine

The two novel bisindole alkaloid structures shown can be synthesized in a few steps from the canthiphytine derivative 9.

Novel, potent and selective cyclin D1/CDK4 inhibitors: Indolo[6,7-a]pyrrolo[3,4-c]carbazoles

The synthesis and CDK inhibitory properties of a series of indolo[6,7-a]pyrrolo[3,4-c]carbazoles is reported. In addition to their potent CDK activity, the compounds display antiproliferative activity against two human cancer cell lines. These inhibitors also effect strong G1 arrest in these cell lines and inhibit Rb phosphorylation at Ser780 consistent with inhibition of cyclin D1/CDK4.

N-(indol-3-ylglyoxylyl)piperidines: High affinity agonists of human GABA-A receptors containing the α1 subunit

A new class of N-(indol-3-ylglyoxylyl)piperidines are high affinity agonists at the benzodiazepine binding site of human GABA-A receptor ion-channels, with modest selectivity for receptors containing the α1 subunit over α2 and α3. All three receptor subtypes discriminate substantially between the two enantiomers of the chiral ligand 10. (C) 2000 Elsevier Science Ltd. All rights reserved.