4942-85-2

Usage

Hexahydroindoloquinolizinone core

The compound has a complex molecular structure featuring a six-membered ring fused to a five-membered ring with a nitrogen atom.

Derivative of ergoline

It is a derivative of the naturally occurring alkaloid, ergoline.

Preccursor to psychoactive substances

It has been identified as a precursor to various psychoactive substances.

Serotonin receptor agonism

It exhibits potential biological activities, including serotonin receptor agonism.

Antipsychotic properties

It also has antipsychotic properties.

Interest in medicinal chemistry and drug discovery

Due to its unique structure and functional properties, it is of interest in the fields of medicinal chemistry and drug discovery.

Ongoing research

Further research into its pharmacological effects and potential therapeutic applications is ongoing.

Upstream product

• 201230-82-2 carbon monoxide 
• 1115302-72-1 N-[2-(1H-indol-3-yl)ethyl]but-3-enamide 
• 388091-45-0 2,5-dioxopyrrolidin-1-yl but-3-enoate 
• 61-54-1 tryptamine 
• 56186-16-4 1-(2-(1H-indol-3-yl)ethyl)-5,6-dihydropyridin-2(1H)-one 
• 76280-18-7 (12bS)-Ethyl 4-oxo-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-3-carboxylate 
• 76280-20-1 4-oxo-1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-3-carboxylic acid 
• 108-55-4 glutaric anhydride, 
• 4787-24-0 methyl 4-(4,9-dihydro-3H-pyrido[3,4-b]indol-1-yl)butanoate 
• 340181-98-8 methyl 5-{[2-(1H-indol-3-yl)ethyl]amino}-5-oxopentanoate 
• 91751-36-9 2,6,7,12-tetrahydroindolo[2,3-a]quinolizin-4(3H)-one 

Relevant academic research and scientific papers

Bioinspired direct access to benzofuroindolines by oxidative [3 + 2] annulation of phenols and indoles

The straightforward entry to benzofuroindoline containing natural product-like scaffolds has been achieved by a challenging [3 + 2] oxidative coupling between phenols and indoles. The reaction proceeds by NIS-oxidation of the indole followed by the trapping of the resulting electrophilic intermediate by phenol.

Palladium-Catalyzed α-Amino C–H Functionalization via Isomerization of α,β-Unsaturated Carbonyls

Palladium-catalyzed regioselective α-amino C–H functionalization via the isomerization of α,β-unsaturated carbonyls including esters, ketones, and amides has been established, providing an easy access to a wide array of tricyclic 1,2,3,4-tetrahydro-b-carb

Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation**

A complementary dual carbonyl activation strategy for the synthesis of polycyclic alkaloids has been developed. Successful applications include the synthesis of tetracyclic alkaloids harmalanine and harmalacinine, pentacyclic indoloquinolizidine alkaloid nortetoyobyrine, and octacyclic β-carboline alkaloid peganumine A. The latter synthesis features a protecting-group-free assembly and an asymmetric disulfonimide-catalyzed cyclization. Furthermore, formal syntheses of hirsutine, deplancheine, 10-desbromoarborescidine A, and oxindole alkaloids rhynchophylline and isorhynchophylline have been achieved. Finally, a concise synthesis of berberine alkaloid ilicifoline B was completed.

Marbostat-100 Defines a New Class of Potent and Selective Antiinflammatory and Antirheumatic Histone Deacetylase 6 Inhibitors

Epigenetic modifiers of the histone deacetylase (HDAC) family contribute to autoimmunity, cancer, HIV infection, inflammation, and neurodegeneration. Hence, histone deacetylase inhibitors (HDACi), which alter protein acetylation, gene expression patterns, and cell fate decisions, represent promising new drugs for the therapy of these diseases. Whereas pan-HDACi inhibit all 11 Zn2+-dependent histone deacetylases (HDACs) and cause a broad spectrum of side effects, specific inhibitors of histone deacetylase 6 (HDAC6i) are supposed to have less side effects. We present the synthesis and biological evaluation of Marbostats, novel HDAC6i that contain the hydroxamic acid moiety linked to tetrahydro-β-carboline derivatives. Our lead compound Marbostat-100 is a more potent and more selective HDAC6i than previously established well-characterized compounds in vitro as well as in cells. Moreover, Marbostat-100 is well tolerated by mice and effective against collagen type II induced arthritis. Thus, Marbostat-100 represents a most selective known HDAC6i and the possibility for clinical evaluation of a HDAC isoform-specific drug.

NOVEL HDAC6 INHIBITORS AND THEIR USES

The present invention relates to small molecule compounds and their use as HDAC inhibitors and in the treatment of various diseases, such as cancer. The present invention further relates to methods of synthesizing the compounds and methods of treatment. H ? L(HA), H is a head group selected from (head group 1), (head group 2), (head group 3), (head group 4), (head group 5) and (head group 6).

Four-component reactions toward fused heterocyclic rings

A multicomponent reaction between H2, CO, an unsaturated carboxylic acid derivative, and binucleophiles has been discovered. This process represents a combination of diversity-oriented synthesis and multicomponent reactions including amidation and hydroformylation, followed by nucleophilic addition to an N-acyliminium ion allowing the generation of six new bonds. Using π-nucleophiles, the sequence turns into a multicomponent Pictet-Spengler reaction.

A general approach to aza-heterocycles by means of domino sequences driven by hydroformylation

The development of hydroformylative domino reactions of easily accessible vinyl acetamides is described. Extremely regioselective hydroformylation of terminal double bounds provides a transient N-acyliminium that can be trapped by various nucleophiles to give several aza-heterocylic scaffolds in a diastereoselective manner.

Regioselective reduction of N-alkyl-3-sulfonylglutarimide. Formal synthesis of 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine and homobaclofen

Reduction of N-alkyl-3-sulfonylglutarimides with (1) sodium hydride and then with lithium aluminum hydride, or (2) sodium borohydride yielded two different types of regioselectively reduced hydroxypiperidinones which were further dehydrated to two pyridin-2-ones in the presence of boron trifluoride etherate. Cycloaddition and regioselective reduction were combined to synthesize 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine and homobaclofen.