64605-23-8

Usage

Uses

Used in Pharmaceutical Industry:
Ethanone, 1-(2-aminophenyl)-2-chloro(9CI) is used as an intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the formation of complex organic molecules that possess therapeutic properties.
Used in Dye Industry:
Ethanone, 1-(2-aminophenyl)-2-chloro(9CI) is utilized as a key component in the production of dyes, where its chemical structure allows for the creation of a wide range of colors and hues.
Used in Organic Synthesis:
Ethanone, 1-(2-aminophenyl)-2-chloro(9CI) is employed as an intermediate in organic synthesis, enabling the creation of a variety of organic compounds for different applications.
Used in Chemical Reactions:
As a reagent, Ethanone, 1-(2-aminophenyl)-2-chloro- (9CI) is used in various chemical reactions to facilitate processes or induce specific chemical changes, contributing to the development of new substances and materials.

InChI:InChI=1/C8H8ClNO/c9-5-8(11)6-3-1-2-4-7(6)10/h1-4H,5,10H2

Upstream product

• 7664-93-9 sulfuric acid 
• 113337-37-4 2-chloro-2'-nitroacetophenone 
• 142-04-1 aniline hydrochloride 
• 107-14-2 chloroacetonitrile 
• 62-53-3 aniline 

Downstream Products

• 817209-39-5 3-chloro-1H-cinnolin-4-one 
• 68095-22-7 N-(2-(2-chloroacetyl)phenyl)acetamide 
• 857948-04-0 chloro-acetic acid-(2-chloroacetyl-anilide) 
• 112978-74-2 N-[2-(2-Chloro-acetyl)-phenyl]-malonamic acid ethyl ester 
• 175657-72-4 2-acetylamino-2-<2-(2-amino-phenyl)-2-oxo-ethyl>-malonic acid diethyl ester 
• 1026012-10-1 2-Acetylamino-2-[2-(2-methylamino-phenyl)-2-oxo-ethyl]-malonic acid diethyl ester 
• 482-89-3 1H,1H'-2,2'-Biindolylidene-3,3'-dione 
• 55968-16-6 2-(2-thienyl)indole 
• 16800-68-3 1-acetyl-2,3-dihydro-1H-indol-3-one 
• 1361967-99-8 1-acetyl-2-((4’-(trifluoromethoxy)biphenyl-4-yl)methylene)indolin-3-one 
• 1361968-00-4 C₂₃H₁₆F₃NO₃ 

Relevant academic research and scientific papers

COMPOUNDS FOR USE IN THE TREATMENT OF BACTERIAL INFECTIONS

The present invention relates to a compound which can be used in the treatment of infections with pathogenic bacteria, in particular pathogens mediating pathogenicity by quinolone dependent production of virulence factors, such as e.g. Pseudomonas aeruginosa and species of the genus Burkholderia, and which can be used for treating bacterial or chronic infections or can be used in combination with other anti-bacterial agents, such as antibiotics, to increase sensitivity of the bacteria for treatment of e.g. multiresistant strains in e.g. mammals.

Azaaurones as Potent Antimycobacterial Agents Active against MDR- and XDR-TB

Herein we report the screening of a small library of aurones and their isosteric counterparts, azaaurones and N-acetylazaaurones, against Mycobacterium tuberculosis. Aurones were found to be inactive at 20 μm, whereas azaaurones and N-acetylazaaurones emerged as the most potent compounds, with nine derivatives displaying MIC99 values ranging from 0.4 to 2.0 μm. In addition, several N-acetylazaaurones were found to be active against multidrug-resistant (MDR) and extensively drug-resistant (XDR) clinical M. tuberculosis isolates. The antimycobacterial mechanism of action of these compounds remains to be determined; however, a preliminary mechanistic study confirmed that they do not inhibit the mycobacterial cytochrome bc1 complex. Additionally, microsomal metabolic stability and metabolite identification studies revealed that N-acetylazaaurones are deacetylated to their azaaurone counterparts. Overall, these results demonstrate that azaaurones and their N-acetyl counterparts represent a new entry in the toolbox of chemotypes capable of inhibiting M. tuberculosis growth.

Synergistic Cooperative Effect of Sodium borohydride-Iodine Towards Cascade C?N and C?S/Se Bond Formation: One-pot Regioselective Synthesis of 3-Sulfenyl/selenyl Indoles and Mechanistic Insight

In this work, a new strategy to synthesize 3-sulfenyl/selenyl indole is reported wherein LC?MS reveals a novel insight into synergistic cooperative effect of NaBH4-I2 which allows cascade C?N and C?S/C?Se bond formations via reduction-nucleophilic cyclization-chalcogenylation, three steps in one-pot, towards regioselective synthesis of diverse 3-chalcogenyl indoles including 5-bromo-3-[(3,4,5-trimethoxyphenyl)thio]-1H-indole, a known lead anticancer compound, directly from 2-amino-phenacylchlorides and thiophenols or disulfides/diselenides in aqueous dioxane under transition-metal-free condition. (Figure presented.).

Competitive Live-Cell Profiling Strategy for Discovering Inhibitors of the Quinolone Biosynthesis of Pseudomonas aeruginosa

Quinolones of the human pathogenPseudomonas aeruginosaserve as antibacterial weapons and quorum sensing signals and coordinate the production of important virulence factors. A central enzyme for the biosynthesis of these quinolones is the synthetase PqsD.

Probing the Azaaurone Scaffold against the Hepatic and Erythrocytic Stages of Malaria Parasites

The potential of azaaurones as dual-stage antimalarial agents was investigated by assessing the effect of a small library of azaaurones on the inhibition of liver and intraerythrocytic lifecycle stages of the malaria parasite. The whole series was screened against the blood stage of a chloroquine-resistant Plasmodium falciparum strain and the liver stage of P. berghei, yielding compounds with dual-stage activity and sub-micromolar potency against erythrocytic parasites. Studies with genetically modified parasites, using a phenotypic assay based on the P. falciparum Dd2-ScDHODH line, which expresses yeast dihydroorotate dehydrogenase (DHODH), showed that one of the azaaurone derivatives has the potential to inhibit the parasite mitochondrial electron-transport chain. The global urgency in finding new therapies for malaria, especially against the underexplored liver stage, associated with chemical tractability of azaaurones, warrants further development of this chemotype. Overall, these results emphasize the azaaurone chemotype as a promising scaffold for dual-stage antimalarials.

Identification, design and biological evaluation of heterocyclic quinolones targeting plasmodium falciparum Type II NADH:Quinone oxidoreductase (PfNDH2)

Following a program undertaken to identify hit compounds against NADH:ubiquinone oxidoreductase (PfNDH2), a novel enzyme target within the malaria parasite Plasmodium falciparum, hit to lead optimization led to identification of CK-2-68, a molecule suitab

OXOBENZINDOLIZINOQUINOLINES AND USES THEREOF

The synthesis of aromathecins, substituted 12H-5,l la-diazadibenzo[b,h]fluoren- 11 -ones is described. Use of these cytotoxic compounds and pharmaceutical compositions containing them for the treatment of cancer is described. Two novel processes for the synthesis of this system and a series of 14-substituted aromathecins as novel cytotoxic, topoisomerase I poisons are described.

Synthesis and biological evaluation of 14-(aminoalkyl-aminomethyl)aromathecins as topoisomerase I inhibitors: Investigating the hypothesis of shared structure-activity relationships

The aromathecin topoisomerase I (top1) inhibitors offer promising scaffolds for the development of novel cancer chemotherapeutics. They are 'composites' of the camptothecin and indenoisoquinoline top1 inhibitors. Interestingly, some structure-activity relationship (SAR) overlap between the aromathecins and the indenoisoquinolines has been observed. For both classes, placement of certain polar groups in similar regions of the heteroaromatic system improves top1 inhibitory and antiproliferative activities. A series of water-soluble aromathecins substituted at position 14 with diaminoalkanes of various lengths has been prepared. These compounds all possess similar antiproliferative potency, but a general trend is observed: aromathecins with longer diaminoalkane substituents (>6 carbons) possess lower anti-top1 activity than their smaller counterparts (2-4 carbons), presumably as a result of unfavorable hydrophobic interactions. This trend is also noted with the indenoisoquinolines, revealing additional SAR overlap that supports the hypothesis that there is a 'universal' top1 inhibitor SAR.

Design, synthesis, and biological evaluation of 14-substituted aromathecins as topoisomerase I inhibitors

The aromathecin or "rosettacin" class of topoisomerase I (top1) inhibitors is effectively a "composite" of the natural products camptothecin and luotonin A and the synthetic indenoisoquinolines. The aromathecins have aroused considerable interest following the isolation and total synthesis of 22-hydroxyacuminatine, a rare cytotoxic natural product containing the 12H-5,11a-diazadibenzo[b,h]fluoren-11-one system. We have developed two novel syntheses of this system and prepared a series of 14-substituted aromathecins as novel antiproliferative topoisomerase I poisons. These inhibitors are proposed to act via an intercalation and "poisoning" mechanism identical to camptothecin and the indenoisoquinolines. Many of these compounds possess greater antiproliferative activity and anti-top 1 activity than the parent unsubstituted compound (rosettacin) and previously synthesized aromathecins, as well as greater top1 inhibitory activity than 22-hydroxyacuminatine. In addition to potentially aiding solubility and localization to the DNA-enzyme complex, nitrogenous substituents located at the 14-position of the aromathecin system have been proposed to project into the major groove of the top1-DNA complex and hydrogen-bond to major-groove amino acids, thereby stabilizing the ternary complex.

Two robust, efficient syntheses of [phenyl ring-U-14C]indole through use of [phenyl ring-U- 14C]aniline

Two robust, efficient syntheses of [phenyl ring-U-14C]indole are presented. In the first synthesis, we developed optimum reaction conditions for the Houben-Hoesch alkylation of chloro acetonitrile with aniline. This was found through the screen