65796-52-3

Basic information

• Product Name: 2,3,4,9-tetrahydro-1H-carbazol-6-amine
• Synonyms: 2,3,4,9-tetrahydro-1H-carbazol-6-amine;6,7,8,9-tetrahydro-5H-carbazol-3-amine
• CAS NO: 65796-52-3
• Molecular Formula: C₁₂H₁₄N₂
• Molecular Weight: 186.25296
• Mol File: 65796-52-3.mol

Chemical Properties

• Melting Point: 151-152 °C(Solv: ligroine (8032-32-4))
• Boiling Point: 403.7°C at 760 mmHg
• Flash Point: 226.9°C
• Appearance: /
• Density: 1.233g/cm³
• Vapor Pressure: 9.96E-07mmHg at 25°C
• Refractive Index: 1.718
• PKA: 18.24±0.20(Predicted)
• CAS DataBase Reference: 2,3,4,9-tetrahydro-1H-carbazol-6-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,9-tetrahydro-1H-carbazol-6-amine(65796-52-3)
• EPA Substance Registry System: 2,3,4,9-tetrahydro-1H-carbazol-6-amine(65796-52-3)

Safety Data

• Hazardous Substances Data: 65796-52-3(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry and Drug Discovery:
2,3,4,9-tetrahydro-1H-carbazol-6-amine is used as a compound with potential biological and pharmacological activities for the development of new drugs and therapeutic agents. Its unique structure and properties make it a promising candidate for further research and exploration in this field.
Used in Organic Synthesis:
2,3,4,9-tetrahydro-1H-carbazol-6-amine is used as a building block for the synthesis of other compounds in organic synthesis. Its unique structure and reactivity make it a valuable component in the creation of new chemical entities and materials.
Further research and exploration of 2,3,4,9-tetrahydro-1H-carbazol-6-amine's properties and potential applications are warranted to fully understand and harness its capabilities in various industries.

InChI:InChI=1/C12H14N2/c13-8-5-6-12-10(7-8)9-3-1-2-4-11(9)14-12/h5-7,14H,1-4,13H2

Upstream product

• 100-63-0 phenylhydrazine 
• 636-99-7 4-nitrophenylhydrazine hydrochloride 
• 100-16-3 4-nitrophenylhydrazone 
• 108-94-1 cyclohexanone 
• 109690-31-5 N-(5,6,7,8-tetrahydro-carbazol-3-yl)-acetamide 
• 50823-86-4 6-nitro-2,3,4,9-tetrahydro-1H-carbazole 
• 3077-85-8 3-Nitro-carbazol 
• 942-01-8 1,2,3,4-tetrahydrocarbazole 

Downstream Products

• 6377-12-4 3-amino-9H-carbazole 
• 1240-34-2 4-methyl-N-(2,3,4,9-tetrahydro-1H-carbazol-6-yl)benzenesulfonamide 
• 110146-03-7 N-(2,3,4,9-tetrahydro-1H-carbazol-6-yl)benzamide 

Relevant articles and documents

Synthesis and evaluation of 2,3,4,9-tetrahydro-1H-carbazole derivatives as selective acetylcholinesterase inhibitors: Potential anti-Alzheimer's agents

Alzheimer's disease is an irreversible, progressive brain disorder that slowly destroys memory and cognition skills. Dysfunction of acetylcholine containing neurons in the brain contributes substantially to the cognitive decline observed in Alzheimer's disease. Hence, our focus is to synthesize cholinesterase inhibitors. A series (22 compounds) of 6- and 9-substituted derivatives of 2,3,4,9-tetrahydro-1H-carbazole have been prepared and in vitro evaluated for acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition by Ellman's method. By comparing selectivity with standard drug donepezil, amino derivative 3, methylamino derivative 4 and butyl nitro derivative 17 have been found to be selective AChE inhibitors. Borsche-Drechsel cyclization reaction has been carried out to synthesize 2,3,4,9-tetrahydrocarbazole ring followed by nitration, reduction and derivative synthesis.

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.

Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases

The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

COMPOSITIONS FOR TREATMENT OF CYSTIC FIBROSIS AND OTHER CHRONIC DISEASES

The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

Modulators of ATP-binding cassette transporters

Compounds of the present invention and pharmaceutically acceptable compositions thereof, are useful as modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator (“CFTR”). The present invention also relates to methods of treating ABC transporter mediated diseases using compounds of the present invention.

2,4-Dimethyl-6H-pyrido[3,2-b]carbazole, an isomer of the antitumor alkaloid ellipticine via the Combes-Beyer reaction

The synthesis of 2,4-dimethyl-6H-pyrido[3,2-b]carbazole (2a) and of its 9-methoxy (2b) and 9-hydroxy (2c) derivatives via the Combes-Beyer reaction is described. Pyridocarbazole 2a has been obtained by two different routes. In the course of the synthesis of 2b either a partial or a total demethoxylation has been observed depending on the route employed.

7-(Substituted)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamines

Pyrrolo[3,2-f]quinazoline-1,3-diamine and the 7-(substituted) and 7,8-disubstituted derivatives thereof, possess anti-bacterial activity in vitro. The invention also provides compounds having other biological effects, such as synergism in vivo with sulfa drugs against bacterial infections, activity in vivo against malarial infections, and anti-cancer activity in vivo. In addition, the compounds show anti-folic acid activity in in vitro tests.