13070-45-6

Usage

Uses

Used in Pharmaceutical Industry:
6-Methoxy-1,2,3,4-tetrahydrocarbazole is utilized as a pharmaceutical compound for its potential antioxidant properties, which can help in combating oxidative stress-related conditions. Its anti-inflammatory capabilities make it a candidate for treating inflammation-based disorders.
Used in Neurological Disorder Treatment:
In the field of neurology, 6-Methoxy-1,2,3,4-tetrahydrocarbazole is being explored as a potential treatment for neurological disorders due to its possible neuroprotective effects.
Used in Organic Synthesis:
6-Methoxy-1,2,3,4-tetrahydrocarbazole is used as a building block in organic synthesis for the preparation of other functionalized tetrahydrocarbazole derivatives, which can have various applications in different chemical and pharmaceutical domains.

Upstream product

• 3449-49-8 6-methoxy-2,3,4,9-tetrahydro-1H-carbazol-1-one 
• 108-94-1 cyclohexanone 
• 3471-32-7 4-Methoxyphenylhydrazine 
• 931-17-9 1,2-Cyclohexanediol 
• 104-94-9 4-methoxy-aniline 
• 1056477-06-5 2-bromocyclohexanone 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 1122-60-7 1-nitrocyclohexane 
• 5345-54-0 3-chloro-4-methoxyaniline 
• 83696-90-6 4-(5-methoxy-1H-indol-3-yl)butyric acid 
• 108-85-0 1-bromocyclohexane 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 1279722-91-6 C₁₃H₁₇NO 
• 935-50-2 4,4-dimethoxycyclohexa-2,5-dienone 

Downstream Products

• 18992-85-3 3-methoxycarbazole 
• 75457-24-8 (+/-)-6-methoxy-(4ar,9ac)-1,2,3,4,4a,9a-hexahydro-carbazole 
• 1313809-56-1 1,6-dimethoxy-9-(4-methoxybenzyl)-1,2,3,4-tetrahydro-9H-carbazole 
• 1313809-69-6 6-methoxy-9-(4-methoxybenzyl)-1,2,3,4-tetrahydro-9H-carbazole 
• 7384-07-8 3-Hydroxycarbazol 

Relevant academic research and scientific papers

Antimony (III) sulfate catalyzed one-pot synthesis of 2,3- disubstitutedindoles

A novel one-pot Fischer indole synthesis approach has been developed by using antimony (III) sulfate as the catalyst. Good yields were obtained after reacting phenylhydrazines hydrochlorides and ketones in refluxing methanol. The exclusive formation of 2,3- disubstituted indoles was observed in the reaction of ethyl methyl ketone with phenylhydrazines. One-pot synthesis of indole-3-propanol using dihydropyran has also been described. The use of reusable antimony (III) sulfate as a catalyst makes this method both economically and environmentally friendly.

Novel benzopsoralen analogues: Synthesis, biological activity and molecular docking studies

New benzopsoralen analogues were synthesized and their inhibitory effect on the growth of tumourtumour cell lines (MDA MB231 and TCC-SUP) was evaluated. The in vitro antitumour activity of the new benzopsoralen analogues was discussed in terms of structure-activity relationship. Molecular docking studies with human-CYP2A6 enzymes were also carried out with the synthesized compounds to evaluate the potential of these molecules to interact with the haem group of the enzymes. The results demonstrated that the compounds that are able to interact with the iron ion of the haem cofactor and at the same time with active site Asn297 are those that have better anti-proliferative activity.

Novel and Efficient Heterogeneous 4-Methylbenzenesulfonic Acid-Based Ionic Liquid Supported on Silica Gel for Greener Fischer Indole Synthesis

In this work, a functionalizing active species 4-methylbenzenesulfonic acid-based IL on silica gel (IL-SO3H-SiO2) has been prepared, and characterized by FT-IR, XRD, TGA, SEM and EDX spectra. Then, IL-SO3H-SiO2 was utilized as an efficient and heterogeneous catalyst for the synthesis of indoles via the one-pot Fischer reaction of phenyl hydrazines with ketones or aldehydes at room temperature. The heterogeneous catalyst could be recovered easily by filtration and reused many times without significant loss of its catalytic activity.

Microwave-assisted one-pot synthesis of 1,2,3,4-tetrahydrocarbazoles

A series of 1,2,3,4-tetrahydrocarbazoles 3a-m were synthesized by the reaction of substituted 2-bromocyclohexanones 2a-c with appropriate anilines 1a-i under microwave irradiation without any other catalysts. Copyright Taylor & Francis Group, LLC.

Design, synthesis, in vivo and in vitro studies of 1,2,3,4-tetrahydro-9H-carbazole derivatives, highly selective and potent butyrylcholinesterase inhibitors

Abstract: Inhibition of butyrylcholinesterase (BChE) might be a useful therapeutic target for Alzheimer’s disease (AD). A new series of 1,2,3,4-tetrahydro-9H-carbazole derivatives were designed synthesized and evaluated as BChE inhibitors. While all of the derivatives have shown for AChE IC50 values below the detectable limit (> 100?μM), they were selective potent BChE inhibitors. 1-(2-(6-fluoro-1,2,3,4-tetrahydro-9H-carbazole-9-yl)ethyl)piperidin-1-ium chloride (15?g) had the most potent anti-BChE activity (IC50 value = 0.11?μM), the highest BChE selectivity and mixed-type inhibition. Pharmacokinetic properties were accordant to Lipinski rule and compound 15g demonstrated neuroprotective and inhibition of β-secretase (BACE1) activities. Furthermore, in vivo study of compound 15g in Morris water maze task has confirmed memory improvement in scopolamine-induced impairment. All results suggest that new sets of potent selective inhibitors of BChE have a therapeutic potential for the treatment of AD. Graphical abstract: A new series of 1,2,3,4-tetrahydro-9H-carbazole derivatives were designed synthesized and evaluated as BChE inhibitors. While all of the derivatives have shown for AChE IC50 values below the detectable limit, they were selective potent BChE inhibitors. Compound 15g had the most potent anti-BChE activity. All results suggest that new sets of potent selective inhibitors of BChE have a therapeutic potential for the treatment of AD.[Figure not available: see fulltext.]

Efficient and straightforward synthesis of tetrahydrocarbazoles and 2,3-dimethyl indoles catalyzed by CAN

A simple protocol was established to synthesize 2,3-dialkyl indoles and various tetrahydrocarbazoles via Fischer indole synthesis. This method uses ceric ammonium nitrate as a catalyst for the Fischer indole synthesis with substituted phenyl hydrazine hydrochlorides and 2-butanone, phenyl propanal, and cyclohexanone. This process is a practical synthetic method for the preparation of various 2,3-disubstituted alkyl indoles and tetrahydrocarbazoles. Copyright Taylor & Francis Group, LLC.

Bismuth nitrate promoted fischer indole synthesis: A simple and convenient approach for the synthesis of alkyl indoles

A novel one-pot fisher indole synthesis approach has been developed by using bismuth nitrate as a catalyst. Yields around 90-95% were obtained after reaction in methanol at reflux temperature in 20-40 min. Apart from the mild reaction conditions of the process and its excellent results, the simplicity of product isolation and the possibility to recycle the bismuth nitrate offers a significant advantage.

Acceptorless dehydrogenative condensation: synthesis of indoles and quinolines from diols and anilines

The use of diols and anilines as reagents for the preparation of indoles represents a challenge in organic synthesis. By means of acceptorless dehydrogenative condensation, heterocycles, such as indoles, can be obtained. Herein we present an experimental and theoretical study for this purpose employing heterogeneous catalysts Pt/Al2O3and ZnO in combination with an acid catalyst (p-TSA) and NMP as solvent. Under our optimized conditions, the diol excess has been reduced down to 2 equivalents. This represents a major advance, and allows the use of other diols. 2,3-Butanediol or 1,2-cyclohexanediol has been employed affording 2,3-dimethyl indoles and tetrahydrocarbazoles. In addition, 1,3-propanediol has been employed to prepare quinolines or natural and synthetic julolidines.

Direct Synthesis of Indoles from Azoarenes and Ketones with Bis(neopentylglycolato)diboron Using 4,4′-Bipyridyl as an Organocatalyst

Multifunctionalized indole derivatives were prepared by reducing azoarenes in the presence of ketones and bis(neopentylglycolato)diboron (B2nep2) with a catalytic amount of 4,4′-bipyridyl under neutral reaction conditions, where 4,4′-bipyridyl acted as an organocatalyst to activate the B-B bond of B2nep2 and form N,N′-diboryl-1,2-diarylhydrazines as key intermediates. Further reaction of N,N′-diboryl-1,2-diarylhydrazines with ketones afforded N-vinyl-1,2-diarylhydrazines, which rearranged to the corresponding indoles via the Fischer indole mechanism. This organocatalytic system was applied to diverse alkyl cyclic ketones, dialkyl, and alkyl/aryl ketones, including heteroatoms. Methyl alkyl ketones gave the corresponding 2-methyl-3-substituted indoles in a regioselective manner. This protocol allowed us to expand the preparation of indoles having high compatibility with not only electron-donating and electron-withdrawing groups but also N- and O-protecting functional groups.

PYRIDINE BASED IONIC FLUORIDE FOR CATALYZING INDOLE AND TETRAZOLE FORMATION

A pyridine based ionic liquid with a fluoride counter anion which catalyzes Fischer indole reaction and click chemistry. Methods of preparing the ionic liquid, and methods of utilizing the ionic liquid as a catalyst to synthesize indoles/indolenines and tetrazoles are also provided.