177841-07-5

Upstream product

• 73568-25-9 2-chloro-3-quinoline carboxaldehyde 
• 1777-53-3 1-(p-tolyl)-2-(triphenylphosphoranylidene)ethanone 
• 122-00-9 para-methylacetophenone 
• 125917-60-4 2-chloro-3-(hydroxymethyl)quinoline 
• 103-84-4 Acetanilid 

Downstream Products

• 1316303-95-3 2-chloro-3-[3-(4-methylphenyl)-4,5-dihydroisoxazol-5-yl]quinoline 
• 1316311-81-5 6-(2-chloroquinolin-3-yl)-4-p-tolyl-6H-1,3-oxazin-2-amine 

Relevant academic research and scientific papers

An efficient synthesis of novel functionalized benzo[h]pyrano[2,3-b]quinolines and pyrano[2,3-b]quinoline derivatives via one-pot multicomponent reactions

In this paper, a convenient, one-pot, for the straightforward synthesis of pyrano[2,3-b]quinoline and benzo[h]pyrano[2,3-b]quinoline derivatives is presented, which includes a three-component reaction of (2-chloroquinoline-3-carbaldehyde, 2-chlorobenzo[h]quinoline-3-carbaldehyde), and 1-phenyl-2-(1,1,1-triphenyl-λ5- phosphanylidene)ethan-1-one (Wittig reagent) with the active methylene compounds such as (benzoylacetonitrile, dimedone, 1,3-dimethylbarbituric acid, 4-hydroxycoumarin and 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one), during the two processes of C–C bond formation (Michael addition) and intramolecular cyclization (by the attack of the oxygen atom of active methylene compounds). Advantages of this protocol include easily accessible starting materials, excellent yields (65–98%), absence of a metal catalyst and simple workup procedure (the pure products were obtained simply by washing the products with EtOH). Graphic abstract: A series of pyrano[2,3-b]quinoline and benzo[h]pyrano[2,3-b]quinoline derivatives have been synthesized in excellent yields (65–98%) via a one-pot three-component reaction of (2-chloroquinoline-3-carbaldehyde, 2-chlorobenzo[h]quinoline-3-carbaldehyde) and 1-phenyl-2-(1,1,1-triphenyl-λ5-phosphanylidene)ethan-1-one (Wittig reagent) with the active methylene compounds such as (benzoylacetonitrile, dimedone, 1,3-dimethylbarbituric acid, 4-hydroxycoumarin and 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one), during the two processes of C–C bond formation (Michael addition) and intramolecular cyclization (by the attack of the oxygen atom of active methylene compounds). Advantages of this protocol include easily accessible starting materials, excellent yields (65–98%), absence of a metal catalyst and simple workup procedure (the pure products were obtained simply by washing the products with EtOH). [Figure not available: see fulltext.]

Synthesis, characterization, and biological applications of pyrazole moiety bearing osmium(IV) complexes

Osmium (IV) complexes with pyrazole nucleus containing ligands were synthesized. Os(IV) compounds were characterized using ESI-MS, ICP-OES, IR spectroscopy, electronic spectroscopy, conductance, and magnetic measurements. Whereas, ligands were characterized by heteronuclear spectroscopy, (1H and 13C), IR spectroscopy, and elemental analysis. All the compounds were tested for their potential to interact with HS-DNA by absorption titration, fluorescence spectroscopy, viscosity measurement, and docking study. The quenching constant and Stern Volmer constant values were calculated using fluorescence study. The synthesized compounds were studied for in-vitro bacteriostatic and cytotoxic activities. The cancer cell line studies of all the synthesized complexes were carried out on human lung cancer cells (A549). Supplemental data for this article is available online at https://doi.org/10.1080/15257770.2021.1921795.

Facile Synthesis of 2-Acylthieno[2,3- b]quinolines via Cu-TEMPO-Catalyzed Dehydrogenation, sp2-C-H Functionalization (Nucleophilic Thiolation by S8) of 2-Haloquinolinyl Ketones

An efficient, solvent-free synthesis of 2-acylthieno[2,3-b]quinolines is reported from 2-halo-quinolinyl ketones through Cu-TEMPO catalyzed dehydrogenation, sp2-C-H functionalization using elemental sulfur as thiol surrogate (sulfur source) and tetrabutylammonium acetate as an ionic reaction medium. The optimized reaction conditions give excellent product yields under mild reaction conditions with chemoselectivity and broad functional group tolerance. The synthetic importance of the synthesized molecules is showcased further by Friedl?nder annulation, reduction, and alkene functionalization reactions.

Synthesis and molecular docking studies of quinoline derivatives as HIV non-nucleoside reverse transcriptase inhibitors

Quinoline moiety is an important scaffold in the field of drug discovery and drug development, with a wide range of pharmacological activities. Quinoline derivatives are potent inhibitors for reverse transcriptase, which is responsible for the conversion of single-stranded viral RNA into double-stranded viral DNA.In the present study, we have designed and synthesized 2 series, namely pyrazoline and pyrimidine containing quinoline derivatives as non nucleoside reverse transcriptase inhibitors (NNRTIs). Eleven compounds were synthesized and characterized by 1H and 13C NMR and mass spectrophotometry. The synthesized compounds were also docked on an HIV reverse transcriptase binding site (PDB: 4I2P); most of these compounds showed good binding interactions with the active domain of the receptor. Most of the compounds displayed a docking score higher than those of standard drugs. Among the synthesized quinoline derivatives, compound 4 exhibited the highest docking score (-10.675).

Efficient Continuous-Flow Synthesis and Evaluation of Anticancer Activity of Novel Quinoline–Pyrazoline Derivatives

Abstract: An efficient and simple continuous-flow synthetic protocol for novel quinoline-tethered pyrazoline derivatives, which involves condensation of 2-chloroquinoline-3-carbaldehydewith arylmethyl ketones followed by cyclisation with phenyl hydrazine,

Synthesis and antimicrobial activity of novel quinoline derivatives bearing pyrazoline and pyridine analogues

The present investigation is in the interest of some synthesized novel derivatives containing (5-(2-chloroquinolin-3-yl)-3-(aryl)-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-4-yl)methanones (4a–o) moieties incorporated with different biological active heterocycles such as quinoline, pyrazoline and pyridine derivatives. For the determination of the compounds reported in this paper was based on IR, 1H NMR, 13C NMR and mass spectral data and same compounds were screened for their antibacterial and antifungal activity on four bacteria (Staphylococcus aureus, Streptococcus pyogenes, Escherichia coli, Pseudomonas aeruginosa) and three fungi (Candida albicans, Aspergillus niger, Aspergillus clavatus) using ampicillin and griseofulvin as the standard drugs. Cytotoxicity study was carried out using MTT colorimetric assay (HeLa cell line). Among the screened compounds, 4e, 4f and 4n showed most potent antibacterial activity, while compounds 4d and 4g emerged as the most active against fungal strains. The results demonstrated that compound 4o was remarkably active against all microbial strains. From the viewpoint of SAR studies, it was observed that the presence of electron withdrawing groups remarkably enhanced the antimicrobial activity of synthesized compounds. Additionally, preliminary MTT cytotoxicity studies on HeLa cells suggested that effective antimicrobial activity of 4e–g, 4n and 4o was accompanied by low cytotoxicity.

An efficient one-pot synthesis and photoinduced DNA cleavage studies of 2-chloro-3-(5-aryl-4,5-dihydroisoxazol-3-yl)quinolines

4,5-Dihydroisoxazoles continue to attract considerable interest due to their wide spread biological activities. Here, we identify an efficient protocol for the preparation of 4,5-dihydroisoxazoles (2-isaxazolines) (4a-g) from quinolinyl chalcones. The nuc

Benign methodology and improved synthesis of 5-(2-chloroquinolin-3-yl)-3- phenyl-4,5-dihydroisoxazoline using acetic acid aqueous solution under ultrasound irradiation

In the present paper, we have executed the synthesis of substituted 5-(2-chloroquinolin-3-yl)-3-phenyl-4,5-dihydroisoxazolines via the reactions of substituted 3-(2-chloroquinolin-3-yl)-1-phenylprop-2-en-1-ones with hydroxylamine hydrochloride and sodium

Novel oxazine skeletons as potential antiplasmodial active ingredients: Synthesis, in vitro and in vivo biology of some oxazine entities produced via cyclization of novel chalcone intermediates

A novel series of 6-(2-chloroquinolin-3-yl)-4-substituted-phenyl-6H-1,3- oxazin-2-amines were synthesized and evaluated for in vitro antimalarial efficacy against chloroquine sensitive (MRC-02) as well as chloroquine resistant (RKL9) strains of Plasmodium