201420-31-7

Usage

Uses

Used in Pharmaceutical Synthesis:
6-Bromo-4-chloroquinoline-3-carbaldehyde is used as a key intermediate in the synthesis of various pharmaceuticals, particularly for the development of potential antimalarial and antiviral agents. Its unique structure and reactivity contribute to the discovery of new therapeutic agents with improved efficacy and safety profiles.
Used in Agrochemical Synthesis:
In the agrochemical industry, 6-Bromo-4-chloroquinoline-3-carbaldehyde serves as a building block for the synthesis of bioactive compounds with pesticidal properties. Its incorporation into agrochemical formulations can lead to the development of more effective and environmentally friendly solutions for crop protection.
Used as a Reagent in Chemical Reactions:
6-Bromo-4-chloroquinoline-3-carbaldehyde is utilized as a reagent in various chemical reactions, facilitating the synthesis of other biologically active compounds. Its versatility in chemical transformations makes it a valuable tool for researchers in the field of medicinal and synthetic chemistry.
Used in the Synthesis of Biologically Active Compounds:
Due to its unique structure, 6-Bromo-4-chloroquinoline-3-carbaldehyde is employed as a starting material for the synthesis of a wide range of biologically active compounds. These compounds can be further explored for their potential applications in various therapeutic areas, including oncology, infectious diseases, and other medical conditions.

Upstream product

• 551-93-9 2-aminoacetophenone 
• 68-12-2 N,N-dimethyl-formamide 
• 206257-39-8 6-bromo-4-chloroquinoline-3-carboxylic acid ethyl ester 
• 122794-99-4 6-bromo-4-hydroxyquinoline-3-carboxylic acid ethyl ester 
• 101937-44-4 diethyl 2-((4-bromophenylamino)methylene)malonate 
• 106-40-1 4-bromo-aniline 
• 29124-64-9 N-(2-acetyl-4-bromophenyl)acetamide 
• 29124-56-9 1-(2-amino-5-bromophenyl)ethanone 

Relevant academic research and scientific papers

Novel D-π-A organic dyes for DSSCs based on dibenzo[b,h][1,6]naphthyridine as a π-bridge

A new series of D-π-A organic dyes bearing fused dibenzo[b,h] [1,6]naphthyridine as the conjugated π-bridge, a cyanoacrylic acid moiety as the electron acceptor/anchoring group and different electron donor groups such as trimethoxy (5a), methoxy (5b) and

2H-Pyrano[3,2-c]quinolin-2-ones: their convenient synthesis and selected reactions

Abstract: Despite the structure attractiveness of 2H-pyrano[3,2-c]quinolin-2-ones 3 their synthesis is not sufficiently developed. Only 35 pyranoquinolinones 3 are registered in the SciFinder database. Unavailability of 3 limits their chemistry exploitation, physical and biological studies. We have developed a convenient and general methodology for the synthesis of 3. Sixteen novel 2H-pyrano[3,2-c]quinolin-2-ones 3 were prepared by a cyclocondensation of easily available 4-oxo-1,4-dihydroquinoline-3-carbaldehydes 1 with monosubstituted acetic acids 2 (-aryl, -arylthio and -heteroaryl). To support chemistry exploitation of pyranoquinolinones 3, oxoquinolinylphenylacrylic acids 4 were obtained by hydrolysis of 3 with NaOH (92–98%). A simple oxidation of 3 by MCPBA was performed to provide oxopyranoquinoline N-oxide 5 (71%). Convenient rearrangement of 5 in refluxing Ac2O curried out 2H-pyrano[3,2-c]quinoline-2,5(6H)-dione 6 in 87% yield. Moreover, some of the prepared pyranoquinolinones 3 possess intensive blue fluorescence properties. Here we described the simple and general synthesis that allows availability of 2H-pyrano[3,2-c]quinolin-2-ones 3. Some transformations of 3 to the novel heterocyclic compounds 4–6 were performed as well in good yields (71–98%). The synthesis of 6 from 3 was not yet described. The developed methodology for the synthesis of 3–6 can stimulate their further physical and pharmacological studies. Graphical Abstract: [Figure not available: see fulltext.].

Synthesis of (2-Aminophenyl)(naphthalen-2-yl)methanones via Intramolecular Rearrangement of (E)-3-Styrylquinolin-4(1 H)-ones under Irradiation with 365 nm UV Light

A highly efficient and environmentally friendly synthesis of (2-aminophenyl)(naphthalen-2-yl)methanones was developed. The (2-aminophenyl)(naphthalen-2-yl)methanone derivatives were obtained in high yields (up to 96%) by the irradiation of (E)-3-styrylquinolin-4(1 H)-ones in EtOH-H 2 O (7:1) with UV light (365 nm) at room temperature under Ar atmosphere. The demonstrated photoinduced intramolecular rearrangement has advantages over other transition-metal-catalyzed reactions, e.g. no requirement of additives, green solvent, broad substrate scope, and high atom efficiency.

Efficient Synthesis of 1,9-Substituted Benzo[h][1,6]naphthyridin-2(1H)-ones and Evaluation of their Plasmodium falciparum Gametocytocidal Activities

A novel three-component, two-step, one-pot nucleophilic aromatic substitution (SNAr)-intramolecular cyclization-Suzuki coupling reaction was developed for the synthesis of benzo[h][1,6]naphthyridin-2(1H)-ones (Torins). On the basis of the new efficiently convergent synthetic route, a library of Torin analogs was synthesized. The antimalarial activities of these compounds were evaluated against asexual parasites using a growth inhibition assay and gametocytes using a viability assay.

Fused ring compound and preparation method, application and intermediate compound thereof

The invention relates to a fused ring compound and a preparation method, application and intermediate compound thereof. The fused ring compound can be used as an inhibitor of phosphatidylinositol 3-kinase.

METHOD OF BLOCKING TRANSMISSION OF MALARIAL PARASITE

The invention provides a method of blocking transmission of a Plasmodium parasite and a method of treating or preventing malaria comprising administering to an animal an effective amount of a first compound of formula I: wherein A, B, R1, R2, R10, and R11 are described herein, either alone or in combination with a second compound selected from elesclomol, NSC 174938, NVP-AUY922, Maduramicin, Narasin, Alvespimycin, Omacetaxine, Thiram, Zinc pyrithione, Phanquinone, Bortezomib, Salinomycin sodium, Monensin sodium, Dipyrithione, Dicyclopentamethylene-thiuram disulfide, YM155, Withaferin A, Adriamycin, Romidepsin, AZD-1 152-HQPA, CAY10581, Plicamycin, CUDC-101, Auranofin, Trametinib, GSK-458, Afatinib, and Panobinostat.

A novel one-pot synthesis of 4-chloro-3-quinolinecarboxaldehydes, 4-chloroquinolines and 4-chloro-3-ethylquinolines using Vilsmeier reagent

Various substituted l-(2-aminophenyl)ethanones on treatment with Vilsmeier reagent at 90°C for 3-6 hr yield 4-chloro-3-quinolinecarboxaldehydes. Whereas substituted N-[2-(1- oxoethyl) phenyl] acetamides afford both 4-chloroqui-nolines and 4-chloro-3-quinolinecarboxaldehydes. However, in the case of substituted l-(2-aminophenyl)butanones and N-[2(1-oxopropyl) phenyl] acetamides, only 4-chloro-3-ethylquinolines are obtained.