2436-04-6

Usage

Synthesis Reference(s)

Synthetic Communications, 23, p. 1689, 1993 DOI: 10.1080/00397919308011267

InChI:InChI=1/C11H14N2O.ClH/c1-14-10-4-2-3-9-8(5-6-12)7-13-11(9)10;/h2-4,7,13H,5-6,12H2,1H3;1H

Upstream product

• 3189-22-8 7-methoxy-1H-indole 
• 109021-64-9 8-methoxy-1-oxo-1,2,3,4-tetrahydro-β-carboline 
• 109021-59-2 7-methoxy-1H-indole-3-carbaldehyde 
• 32464-55-4 2-(4,4-diethoxybutyl)isoindoline-1,3-dione 
• 16990-42-4 3-(2-nitrovinyl)-7-methoxy-1H-indole 
• 148336-59-8 7-methoxyindole-3-glyoxylamide 
• 50656-47-8 7-methoxyindole-3-glyoxyl chloride 
• 96096-68-3 β-pyrrolidino-2-nitro-3-methoxystyrene 
• 96096-62-7 3-(2-nitroethyl)-7-methoxyindole 
• 16990-42-4 7-methoxy-3-[(E)-2-nitrovinyl]-1H-indole 
• 18312-46-4 (2-methoxyphenyl)hydrazine 

Downstream Products

• 125160-74-9 N-tosyl-7-methoxy-tryptamine 
• 1631136-30-5 C₂₉H₃₂N₂O₂ 
• 1132682-75-7 C₁₈H₁₈FN₃O₄ 
• 96096-67-2 N-(benzyloxycarbonyl)-7-methoxytryptamine 

Relevant academic research and scientific papers

Preparation of 7-methoxytryptamine

7-Methoxytryptamine (6a) was prepared from cheap and easily available starting materials by using the Abramovitch-Shapiro method

INDOLE AHR INHIBITORS AND USES THEREOF

The present invention provides compounds useful as inhibitors of AHR, compositions thereof, and methods of using the same.

Chiral anion phase transfer of aryldiazonium cations: An enantioselective synthesis of C3-diazenated pyrroloindolines

Herein is reported the first asymmetric utilization of aryldiazonium cations as a source of electrophilic nitrogen. This is achieved through a chiral anion phase-transfer pyrroloindolinization reaction that forms C3-diazenated pyrroloindolines from simple tryptamines and aryldiazonium tetrafluoroborates. The title compounds are obtained in up to 99% yield and 96% ee. The air- and water-tolerant reaction allows electronic and steric diversity of the aryldiazonium electrophile and the tryptamine core. Live and let diazene: Chiral anion phase transfer of aryldiazonium cations has been utilized to prepare C3-diazenated pyrroloindolines. The air- and water-tolerant reaction allows electronic and steric diversity in the aryldiazonium electrophile and the tryptamine core, with the products being obtained in up to 99% yield and 96% ee (MTBE=methyl tert-butyl ether).

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.

Structure-activity relationship study of beta-carboline derivatives as haspin kinase inhibitors

Haspin is a serine/threonine kinase that phosphorylates Thr-3 of histone H3 in mitosis that has emerged as a possible cancer therapeutic target. High throughput screening of approximately 140,000 compounds identified the beta-carbolines harmine and harmol as moderately potent haspin kinase inhibitors. Based on information obtained from a structure-activity relationship study previously conducted for an acridine series of haspin inhibitors in conjunction with in silico docking using a recently disclosed crystal structure of the kinase, harmine analogs were designed that resulted in significantly increased haspin kinase inhibitory potency. The harmine derivatives also demonstrated less activity towards DYRK2 compared to the acridine series. In vitro mouse liver microsome stability and kinase profiling of a representative member of the harmine series (42, LDN-211898) are also presented.

Novel tetrahydro-β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)

A structure-activity relationship study was conducted on a series of tetrahydro-β-carboline-1-carboxylic acid analogs in order to identify the key functionality responsible for activity against the mitogen-activated protein kinase-activated protein kinase 2 enzyme (MK-2). The compounds were further evaluated for their ability to inhibit TNFα production in U937 cells and in vivo. These compounds represent a novel structural class of compounds capable of inhibiting MK-2 with remarkable selectivity.

8-SUBSTITUTED TETRAHYDRO-BETA-CARBOLINES

The present invention provides novel tetrahydro-beta-carboline compounds and intermediates having useful central nervous system activity. The invention provides formulations and methods for using the tetrahydro-beta-carboline and related intermediate compounds. Finally, the invention provides an article of manufacture.

INTERMEDIATES TO TETRAHYDRO-BETA-CARBOLINES

3-Ethanamine and 3-ethanamine related compounds are provided that are useful intermediates and have beneficial central nervous system activity.

METHOD FOR TREATING 5HT2B RECEPTOR RELATED CONDITIONS

The present invention provides methods for binding a 5-HT 2B receptor in mammals using a both known and novel compounds. Further, the invention provides a method for treating or preventing 5-HT 2B related conditions. Finally, the invention provides an article of manufacture.

Tetrahydro-β-carbolines

The present invention provides tetrahydro-betacarboline compounds having useful central nervous system activity.