14192-67-7

Usage

Uses

Used in Pharmaceutical Industry:
6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE is used as a building block for the synthesis of various pharmaceutical drugs and agrochemicals, contributing to the development of new therapeutic agents and agricultural products.
Used in Organic Electronic Materials:
In the field of organic electronic materials, 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE is utilized for its electronic and optical properties, which make it a valuable component in the creation of advanced electronic devices and systems.
Used in Antitumor Research:
6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOL-1-ONE is studied for its potential as an antitumor agent, given its ability to inhibit the growth of cancer cells, offering a promising avenue for cancer treatment and therapeutic development.

InChI:InChI=1/C12H10ClNO/c13-7-4-5-10-9(6-7)8-2-1-3-11(15)12(8)14-10/h4-6,14H,1-3H2

Upstream product

• 78153-20-5 6-chloro-3,4-dihydro-1(2H)-oxo-carbazole-9-carboxaldehyde 
• 14192-45-1 cyclohexane-1,2-dione (4-chlorophenyl)hydrazone 
• 106-47-8 4-chloro-aniline 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 4545-18-0 N'-cyclohexylidene-4-methylbenzene-1-sulfonohydrazide 
• 141091-37-4 2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 89490-05-1 cyclohex-1-enylboronic acid 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 765-87-7 cyclohexane-1,2-dione 
• 108-94-1 cyclohexanone 
• 823-45-0 2-(hydroxymethylene)cyclohexanone 
• 53475-33-5 2-((4-chlorophenyl)amino)cyclohex-2-en-1-one 
• 23740-64-9 2-morpholinocyclohex-2-enone 
• 2028-74-2 p-chlorobenzenediazonium chloride 

Downstream Products

• 121594-05-6 Benzyl-[6-chloro-2,3,4,9-tetrahydro-carbazol-(1E)-ylidene]-amine 
• 121594-06-7 [6-Chloro-2,3,4,9-tetrahydro-carbazol-(1E)-ylidene]-(2-phenoxy-ethyl)-amine 
• 156424-67-8 6-chloro-1-hydroxyimino-1,2,3,4-tetrahydrocarbazole 
• 352553-60-7 6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine 
• 1612188-88-1 2-amino-8-chloro-4-phenyl-5,6-dihydro-11H-benzo[a]carbazole-1,3-dicarbonitrile 
• 1612188-89-2 2-amino-8-chloro-4-(4'-bromo-phenyl)-5,6-dihydro-11H-benzo[a]carbazole-1,3-dicarbonitrile 
• 1612188-90-5 2-amino-8-chloro-4-(4'-dimethylamino-phenyl)-5,6-dihydro-11H-benzo[a]carbazole-1,3-dicarbonitrile 

Relevant academic research and scientific papers

Reactions of methyl 2-(1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl) oxoacetates. Synthesis of methyl isoxazolo[5,4-a]carbazole-3-carboxylates

The reaction of methyl 2-(1-oxo-2,3,4,9-tetrahydro-1H-carbazol-2-yl) oxoacetates (1a-e) with hydroxylamine hydrochloride in alcoholic KOH afforded 1-hydroxyimino-2,3,4,9-tetrahydro-1H-carbazoles (2a-e), and in acetic acid methyl isoxazolo[5,4-a]carbazole-3-carboxylates (3a-e). Ketoesters 1a-e with urea and thiourea under acidic conditions yielded a mixture of the respective 1-hydroxycarbazoles (6a-e) and 2,3,4,9-tetrahydro-1H-carbazol-1-ones (7a-e), but under basic conditions the respective 1-carbimido-and 1-thiocarbimido-2,3,4,9- tetrahydro-1H-carbazoles (8a-e and 9a-e) were formed. Plausible mechanisms are proposed.

An efficient and general synthesis of indolo[2,3-a]carbazoles using the Fischer indole synthesis

Synthetically important indolo[2,3-a]carbazoles were obtained in a one-pot reaction via Fischer indole synthesis starting from 2-amino-cyclohexanone hydrochloride and substituted arylhydrazines hydrochloride in the presence of acidic media.

Synthesis of tricyclic units of indole alkaloids: Application of Fischer indolization and olefin metathesis

Simple synthetic approaches to pyridocarbazole and azepinocarbazole derivatives have been reported via Fischer indolization, Grignard reaction and olefin metathesis as key steps. In addition, a combination Sonogashira coupling and Pauson-Khand reaction has been used to assemble extended pyridocarbazole derivative.

Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles

We describe a cascade strategy for tri- or tetrafunctionalization of alkenylboronic acids to prepare diverse tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles in good yields withN-hydroxybenzotriazin-4-one (HOOBT) and arylhydrazines as oxygen and nitrogen sources, respectively. Mechanistic studies reveal that the domino reaction undergoes the copper-catalyzed Chan-Lam reaction, [2,3]-rearrangement, nucleophilic substitution, oxidation and sequential [3,3]-rearrangement over five steps in a one-pot reaction. The reaction shows a broad substrate scope and tolerates a wide range of functional groups. More importantly, the reaction is easily performed at gram scales and the product is purified by simple extraction, washing, and recrystallization without flash column chromatography. The present protocol features easily available starting materials, high site-marked functionalization, five-step cascade in one pot, multiple C-C/C-O/C-N bond formation, and diversity of indole motifs.

1,3,4,9-TETRAHYDRO-2H-PYRIDO[3,4-B]INDOLE DERIVATIVE COMPOUNDS AND USES THEREOF

The present invention relates to 1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole derivative compounds and uses thereof. In particular, compounds of the invention have antibacterial activity and/or are capable of re-sensitizing methicillin-resistant Staphylococcus aureus to a P-lactam antibiotic or a combination of a P-lactam antibiotic and a P-lactamase inhibitor. The present invention also relates to a method for producing and using said compounds.

Design, synthesis and evaluation of hybrid of tetrahydrocarbazole with 2,4-diaminopyrimidine scaffold as antibacterial agents

Several 6-substituted tetrahydrocarbazole derivatives were designed, synthesized and evaluated for the antibacterial activities against Staphylococcus aureus Newman strain. Subsequently, 2,4-diaminopyrimidine scaffold was merged with the tetrahydrocarbazole unit to generate a series of novel hybrid derivatives and the antibacterial activities were also investigated. Among these novel hybrids, compound 12c showed the most potent activity with a MIC of 0.39–0.78 μg/mL against S. aureus Newman and Escherichia coli AB1157 strain. In addition, compound 12c exhibited low MIC values against a panel of multidrug-resistant strains of S. aureus.

First-generation structure-activity relationship studies of 2,3,4,9-tetrahydro-1H-carbazol-1-amines as CpxA phosphatase inhibitors

Genetic activation of the bacterial two-component signal transduction system, CpxRA, abolishes the virulence of a number of pathogens in human and murine infection models. Recently, 2,3,4,9-tetrahydro-1H-carbazol-1-amines were shown to activate the CpxRA

THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION

Disclosed herein are compounds of formula I: or a salt thereof and compositions comprising a compound of formula I or a pharmaceutically acceptable salt thereof. Also disclosed herein are methods for treating or preventing a bacterial infection in an anim

USE OF A DHODH INHIBITOR IN COMBINATION WITH AN INHIBITOR OF PYRIMIDINE SALVAGE

Compounds and methods are provided for the treatment of pathogenic virus infections or cancer. The formulations combine an inhibitor of de novo pyrimidine synthesis, and an inhibitor of a pyrimidine salvage pathway enzyme.

A diversity-oriented approach to indolocarbazoles: Via Fischer indolization and olefin metathesis: Total synthesis of tjipanazole D and i

New synthetic strategies to indolocarbazoles have been reported via two-fold Fischer indolization under green conditions using l-(+)-tartaric acid and N,N-dimethyl urea. Starting with cyclohexanone, a bench-top starting material, this methodology has been extended to the total synthesis of natural products such as tjipanazoles D and I as well as the core structure of asteropusazole and racemosin B. Here, atom economical reactions like ring-closing metathesis, enyne-metathesis, and the Diels-Alder reaction have been used as key steps. Diverse strategies demonstrated here are useful in medicinal chemistry and materials science to design a library of decorated indoles.