2367-17-1

Usage

Uses

Used in Pharmaceutical Research:
6-Fluoro-2,3,4,9-tetrahydro-1H-carbazole is utilized as a pharmaceutical candidate for its potential anti-inflammatory, anti-cancer, and anti-microbial properties. The presence of the fluorine atom can enhance the compound's activity and selectivity, making it a valuable asset in the development of new drugs.
Used in Organic Synthesis:
In the field of organic synthesis, 6-fluoro-2,3,4,9-tetrahydro-1H-carbazole serves as a key intermediate or building block for the creation of more complex molecules. Its unique structural features allow for the synthesis of novel compounds with tailored properties for various applications.
Used in Drug Development:
6-Fluoro-2,3,4,9-tetrahydro-1H-carbazole is employed in drug development as a potential lead compound. The modification of the carbazole structure through fluorination can result in improved pharmacokinetic and pharmacodynamic profiles, which are crucial for the effectiveness and safety of new medications.
Used in Medicinal Chemistry:
In medicinal chemistry, 6-fluoro-2,3,4,9-tetrahydro-1H-carbazole is used as a template for the design of new therapeutic agents. Its structural properties can be further optimized through chemical modifications to enhance its interaction with biological targets, leading to more potent and selective drugs.
Used in Biochemical Research:
6-Fluoro-2,3,4,9-tetrahydro-1H-carbazole is applied in biochemical research to study the effects of fluorination on the binding affinity and selectivity of carbazole-based compounds towards various biological targets. This research can provide insights into the structure-activity relationships of these compounds and guide the design of more effective drugs.
Used in Chemical Biology:
In chemical biology, 6-fluoro-2,3,4,9-tetrahydro-1H-carbazole is used to probe the interactions between small molecules and biological systems. Its unique structural features can help elucidate the molecular mechanisms underlying various biological processes and diseases, contributing to a better understanding of the underlying chemistry in living organisms.

Upstream product

• 371-14-2 4-fluorophenylhydrazine 
• 108-94-1 cyclohexanone 
• 1202391-84-1 tert-butyl 2-(4-fluorophenyl)hydrazine-1-carboxylate 
• 286-20-4 cyclohexane-1,2-epoxide 
• 371-40-4 4-fluoroaniline 
• 823-85-8 4-fluorophenyhydrazine hydrochloride 
• 367-21-5 3-chloro-4-fluorophenylamine 
• 588-54-5 cyclohexanone-(4-fluoro-phenylhydrazone) 

Downstream Products

• 391-45-7 3-fluoro-9H-carbazole 

Relevant academic research and scientific papers

SBA-15-Pr-SO3H catalyzed one-pot synthesis of indole derivatives via Fischer indole pathway

In this work, an efficient, user-friendly, and simple procedure was reported for the preparation of indole derivatives catalyzed by the heterogeneous SBA-15-Pr-SO3H via Fischer indole pathway. The title compounds were synthesized from various arylhydrazines and ketones in the presence of 3 mol% of the catalyst in the refluxing ethanol.

5,6-Bis(9-(2-decyltetradecyl)-6-fluoro-9H-carbazol-3-yl)naphtho[2,1-b:3,4-b']dithiophene as a Promising Donor Structure for D–A Conjugated Copolymers with a Narrow Bandgap

A new carbazole-containing naphthodithiophene derivative—heteroaromatic compound 5,6- bis[9-(2-decyltetradecyl)-9H-carbazol-3-yl]naphtho[2,1-b:3,4-b']dithiophene (M1)—has been synthesized. The compound will be used by us as a weak donor structural block for fabricating narrow-bandgap D–A conjugated polymers. The composition and structure of M1 have been confirmed by elemental analysis data, IR spectroscopy, and 1H and 13C NMR. The synthesized compound has a low HOMO energy (–5.4 eV), which is favorable for a high open-circuit voltage. Monomer M1 can be used as a promising weak donor moiety in D–A conjugated polymers for solar photovoltaics.

Tetrahydrocarbazoles by mechanochemical Fischer indolisation

The Fischer indolisation (FI) typically proceeds in the presence of a Br?nsted or Lewis acid in an organic solvent at elevated temperatures. Herein, we report that tetrahydrocarbazoles (THCs) are accessible by mechanochemical FI at ambient temperature. Using phenylhydrazine hydrochlorides in the presence of silica is critical for this solid-state variant of the FI.

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.]

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.

Copper(II) catalyzed aromatization of tetrahydrocarbazole: An unprecedented protocol and its utility towards the synthesis of carbazole alkaloids

An efficient protocol for the aromatization of tetrahydrocarbazole is described by using catalytic copper(II) chloride dihydrate in DMSO. This newly established methodology has utilized towards the synthesis of naturally occurring carbazole alkaloids, namely 3-methylcarbazole, 3-formyl carbazole, glycozoline, glycozolicine and clauszoline-K. In addition, the protocol is generalized for the aromatization of N-substituted tetrahydrocarbazole, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and 1,2,3,4-tetrahydro β-carboline to give the corresponding heteroaromatic compounds from very good to excellent yield. Moreover, this method has been proven to be tolerant to a broad range of functional groups with excellent yields.

An Electrophilic Bromine Redox Catalysis for the Synthesis of Indole Alkaloid Building Blocks by Selective Aliphatic C?H Amination

A new homogeneous bromine(?I/I) redox catalysis is described, which is based on monomeric bromine(I) compounds containing transferable phthalimidato groups. These catalysts enable intermolecular C?H amination reactions at previously unaccessible aliphatic positions and thus enlarge the synthetic potential of direct C?N bond formation, including its application in the synthesis of alkaloid building blocks. This aspect is demonstrated by a new synthetic approach to aspidospermidine. In addition to the development of the catalyst system, the structures of the involved bromine(I) key catalysts were fully elucidated, including by X-ray analyses.

Design, synthesis and pharmacological evaluation of some novel tetrahydrocarbazoles as potential COX-2 inhibitors

Background: NSAIDs have been extensively used for the treatment of pain and inflammation. There are about 30 different NSAIDs available in market and about 80 percent of prescriptions throughout the world contains one or the other painkiller. Chronic use of these drugs has many side effects such as gastric ulceration and the COX-2 inhibitors suffer from major drawback of cardiac toxicity. The need for a potential and safe NSAIDs has always led to the development of newer, better and safer drug molecules. In this article design and development of tetrahydrocarbazole derivatives with very low ulcerative index is reported. Methods: Fifteen tetrahydrocarbazole derivatives were synthesized on the basis of structural homology to indomethacin. Compounds were synthesized and characterized on the basis of spectral data. These were studied for their analgesic, anti-inflammatory and ulcerogenic activities. These compounds were subjected to molecular docking studies for understanding the possible mechanism of action and target. Results: The designed compounds were synthesized successfully in good yield and purity without much efforts. All compounds were evaluated by in vitro and in vivo assay, molecular modelling studies and ulcerative index. One of the compound (3-Aminophenyl) (6-chloro-1,2,3,4-tetrahydro-9H-carbazol-9-yl) methanone 13 was found to be highly active in the in vitro and in vivo assessment also it was found to be highly safe on ulcerogenic index compared to the standard drugs. Conclusion: Tetrahydrocarbazoles were found to be promising scaffolds which can be developed into safe and potential non-steroidal anti-inflammatory agents.

N, N -Dimethylpyridin-4-amine (DMAP) based ionic liquids: Evaluation of physical properties via molecular dynamics simulations and application as a catalyst for Fisher indole and 1 H -tetrazole synthesis

The last few decades have seen a rapid increase in the use of ionic liquids (ILs) as a green alternative to traditional solvents in organic synthesis. The use of ILs as catalysts has also increased in recent years. Herein we the report synthesis of new N,N-dimethylpyridin-4-amine (DMAP) based ionic liquids (ILs) as new and efficient catalysts for the facile synthesis of indoles (via Fischer indole synthesis), and 1H-tetrazoles (via click chemistry). The method is environmentally friendly, requiring only minimum catalyst loading (0.2 equiv. for Fischer indole synthesis). In the case of 1H-tetrazole formation (via click chemistry), the reaction was carried out under a solvent free environment. Moreover, thermal studies (TGA, DTG and DSC) of DMAP-ILs (2, 3) have also been carried out to elicit their stability for temperature dependent reactions. Application of molecular dynamics simulations provided valuable insights into the structural and transport properties of these ionic liquids. An MP2 method was applied to evaluate the stability of the compound via binding energy calculations.

Microwave-Assisted Rapid One-Pot Synthesis of Fused and Non-Fused Indoles and 5-[18F]Fluoroindoles from Phenylazocarboxylates

Substituted indoles can be prepared from phenylazocarboxylates through a rapid one-pot sequence featuring a microwave-assisted Fischer indole synthesis as a key step. Considering that the phenylazocarboxylates may beforehand be modified by mild nucleophilic aromatic substitution, including the introduction of [18F]fluoride, the overall strategy offers an attractive new access to 5-[18F]fluoroindoles.