36729-27-8

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4,9-Tetrahydro-1H-carbazole-6-carboxylic Acid is used as a therapeutic agent for targeting the main protease of SARS-CoV-2. This application is significant in the development of treatments and potential inhibitors against the virus responsible for COVID-19, showcasing its importance in the ongoing fight against the pandemic.
As a chemical compound with unique properties, 2,3,4,9-Tetrahydro-1H-carbazole-6-carboxylic Acid may also have potential applications in other industries, such as materials science or chemical research. However, based on the provided materials, the primary use highlighted is its role in the pharmaceutical industry for combating SARS-CoV-2.

InChI:InChI=1/C13H13NO2/c15-13(16)8-5-6-12-10(7-8)9-3-1-2-4-11(9)14-12/h5-7,14H,1-4H2,(H,15,16)/p-1

Upstream product

• 302557-44-4 methyl 2,3,4,9-tetrahydro-1H-carbazole-6-carboxylate 
• 385406-36-0 4-cyclohexylidenehydrazino-benzoic acid 
• 108-94-1 cyclohexanone 
• 619-67-0 4-Hydrazinobenzoic acid 
• 24589-77-3 4-hydrazinobenzoic acid hydrochloride 
• 822-87-7 2-Chlorocyclohexanone 
• 619-45-4 4-methoxycarbonyl aniline 

Downstream Products

• 302557-44-4 methyl 2,3,4,9-tetrahydro-1H-carbazole-6-carboxylate 
• 102237-62-7 9-benzyl-5,6,7,8-tetrahydro-carbazole-3-carboxylic acid 
• 51035-17-7 9H-carbazole-3-carboxylic acid 
• 1392116-44-7 C₂₄H₂₂F₃N₃O₂ 
• 1392116-43-6 C₂₄H₂₃F₂N₃O₃ 
• 1181975-42-7 methyl 9-(3-(((3,5-difluorophenyl)sulfonyl)amino)propyl)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxylate 
• 1007568-25-3 9-(3-benzenesulfonyl-propyl)-5,6,7,8-tetrahydro-9H-carbazole-3-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Discovery of carbazole carboxamides as novel RORγt inverse agonists

A novel series of carbazole carboxamides was discovered as potent RORγt inverse agonists using a scaffold hybridization strategy. Structure-activity relationship exploration on the amide linker, carbazole ring and arylsulfone moiety of the hybrid amide 3a led to identification of potent RORγt inverse agonists. Compound 6c was found to have a good RORγt activity with an IC50 of 58.5 nM in FRET assay, and reasonable inhibitory activity in mouse Th17 cell differentiation assay (58.8% inhibition at 0.3 μM). The binding mode of carbazole carboxamides in RORγt ligand binding domain was discussed.

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.

FUNCTIONALISED AND SUBSTITUTED CARBAZOLES AS ANTI-CANCER AGENTS

The present invention relates to anti-tropomyosin compounds, processes for their preparation, and methods for treating or preventing a disease or disorder, such as a proliferative disease (preferably cancer), using compounds of the invention.

Iodine-catalyzed aromatization of tetrahydrocarbazoles and its utility in the synthesis of glycozoline and murrayafoline A: A combined experimental and computational investigation

A new protocol for the aromatization of tetrahydrocarbazoles has been achieved using a catalytic amount of iodine, giving high yields. The role of iodine in the aromatization has been explained by DFT, and its wide scope is extended to the total synthesis of glycozoline and murrayafoline A. This method has proven to be tolerant of a broad range of functional groups. This journal is the Partner Organisations 2014.

Discovery of ITX 4520: A highly potent orally bioavailable hepatitis C virus entry inhibitor

The manuscript reports an identification of a highly potent, orally bioavailable hepatitis C virus entry inhibitor through optimization of a previously reported class of molecules (1) that were not stable in the rat plasma. Compound 39 (ITX 4520) exhibited an excellent PK profile in both rats and dogs with good oral exposure, half-life and oral bioavailability. The compound is also well-tolerated in the preliminary in vivo toxicity studies and has been selected as a pre-clinical candidate for our HCV clinical pipeline.

Discovery of highly potent small molecule Hepatitis C Virus entry inhibitors

Novel, highly potent small molecule HCV entry inhibitors are reported. The SAR exploration of a hit molecule identified from screening of a compound library led to the identification of highly potent compounds with IC 50 values of 5 nM in the tissue culture HCV infectious assay.

N-Benzyl-indolo carboxylic acids: Design and synthesis of potent and selective adipocyte fatty-acid binding protein (A-FABP) inhibitors

Small molecule inhibitors of adipocyte fatty-acid binding protein (A-FABP) have gained renewed interest following the recent publication of pharmacologically beneficial effects of such inhibitors. Despite the potential utility of selective A-FABP inhibito

DERIVATIVES OF SUBSTITUTED FUSED RING CYCLOINDOLES AND METHODS OF THEIR USE

Disclosed herein are derivatives of substituted fused ring cycloindole useful, inter alia, in combating Hepatitis C infection and entry into cells.

HEPATITIS C VIRUS ENTRY INHIBITORS

The present invention relates to the use of tricyclic diphenylamine derivative compounds for prevention and/or treatment of Hepatitis C virus (HCV) infection by inhibiting HCV entry into permissive cells.

TRICYCLIC CYTOPROTECTIVE COMPOUNDS

Compounds of formula (I): in which: X is a group of formula >CR1R2 or >SO2; Y is a group of formula >NH or >CR1R2; Z is a group of formula >C=O or >CH2 or a direct bond; R1 hydrogen and R2 is hydrogen, carboxy or hydroxy; or R1 and R2 together represent an oxo group, a methylenedioxy group or a hydroxyimino group; R3 is hydrogen or lower alkyl; R4 represents two hydrogen atoms, or an oxo or hydroxyimino group; R5 is hydrogen, lower alkyl or halogen; R6 is hydrogen, lower alkoxy or carboxy; R7 and R8 are each hydrogen, lower alkyl or halogen; and pharmaceutically acceptable salts and esters thereof can be used for the treatment or prophylaxis of acute or chronic neurodegenerative diseases or conditions such as Alzheimer’s Disease, Parkinson’s Disease, Huntington’s Chorea, Multiple Sclerosis or the sequelae to acute ischaemic events such as heart attack, stroke or head injury and for protection against ischaemic damage to tissues of peripheral organs.