One-pot, simple and efficient synthesis of novel bioactive 4-aryl-1,2-dihydro-6-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-oxopyridin-3-carbonitriles via multi-component approach

A new coumarin derivative, (E)-3-(3-(4-(dimethylamino) phenyl) acrylo-yl)-4-hydroxy-2H-chromen-2-one (3), was synthesized by the condensation of 3-acetyl-4-hydroxycoumarin (1) with 4-N,N-dimethylaminobenzaldehyde (2) in the presence of piperidine in ethanol. The structure of the synthesized compound was characterized using spectroscopic data (IR and 1H NMR) and elemental analysis. The antimicrobial properties and acetylcholinesterase inhibition activity (AChEI) of coumarin 3 were investigated, with the highest observed AChEI activity providing 48.25% inhibition. The electronic absorption and emission spectra revealed that 3 exists as two, main keto-enol tautomers. The ratios of these tautomers in both protic and aprotic solvents with different polarities and dielectric constants were calculated. The fluorescence of coumarin 3 was enhanced upon increasing the medium viscosity, which was due to the resultant molecular rigidity. This criterion was further investigated using DNA, whereby 3 showed enhanced fluorescence upon its uptake in DNA grooves and was therefore tested as a novel DNA fluorescent stain.

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“…Coumarin derivatives 1 and 3 were screened for their antibacterial effects, as reported in our previous work [36].…”

Section: Antibacterial Activitymentioning

confidence: 99%

Synthesis and Spectral Characterisation of (E)-3-(3-(4 (Dimethylamino)Phenyl)Acrylo-yl)-4-Hydroxy-2H-Chromen-2-One and Their Antibacterial Activity and Acetylcholinesterase Inhibition

Slimani

Hamdi

Al-Hazmy

et al. 2021

Journal of Chemistry

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“…As part of our interest in developing a practical and efficient synthesis method in an environmentally friendly manner [43][44][45], we herein report an alternative, simple route for the synthesis of isoindolin-1-one-3-phosphonates 4. Furthermore, compounds 4 were investigated for their antimicrobial activity against Micrococcus luteus, Listeria monocytogenes, Staphylococcus aureus, Bacillus cereus, Salmonella typhimurium and Candida albicans and for their antiparasitic activity against Leishmania major and Toxoplasama gondii.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and in vitro bioactivity studies of isoindolin‐1‐3‐phosophonate compounds

Jelali

Nasr

Koko

et al. 2022

Journal of Heterocyclic Chem

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In this work, efficient synthesis of isoindolin-1-one-3-phosphonates under catalyst-and solvent-free conditions was reported to afford the desired compounds in excellent yields with potent pharmacological properties. The synthesis method involves the preparation of isoindolin-1-one-3-phosphonates by a "one-pot" three-component reaction of 2-formylbenzoic acid with primary amines and dimethyl phosphite under solvent-and catalyst-free conditions.All new compounds were characterized by 1 H NMR, 13 C NMR, FT-IR and elemental analysis techniques. The compounds were investigated for their bioactivities against a group of microorganisms, Leishmania major, Toxoplasma gondii parasites, and the DA-MB-231 and MCF-7 cancer cell lines in vitro.Compound 4a was found to be the most active against L. M. luteus, L. monocytogenes and C. albicans microorganisms, with inhibition zones of 35, 22 and 38 mm, respectively. The compounds were also investigated for their antiparasitic activities, and compounds 4a and 4b were the most active against L. major amastigotes and promastigotes with EC 50 < 1 μM. All tested compounds had potent anticancer activity against the MDA-MB-231 and MCF-7 human cell lines with EC 50 < 1.5 μM. Compounds 4a and 4b are good drug candidates for antimicrobial, antileishmanial and anticancer drug discovery, and further in vivo studies are highly recommended prior to any clinical trials.

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“…The hydroxyl groups found in the phenolic compounds have been granted a vital place in medicinal chemistry because they are responsible for anti-oxidant, antiviral, antimicrobial, insecticidal, anti-sclerotic, anti-parasitic and hypoglycemic biological activities, among others. The utilization of these derivatives in organic synthesis has become a traditional approach for the preparation of wide range of phenol derivatives [ 17 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

Pyridine Scaffolds, Phenols and Derivatives of Azo Moiety: Current Therapeutic Perspectives

et al. 2021

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Synthetic heterocyclic compounds have incredible potential against different diseases; pyridines, phenolic compounds and the derivatives of azo moiety have shown excellent antimicrobial, antiviral, antidiabetic, anti-melanogenic, anti-ulcer, anticancer, anti-mycobacterial, anti-inflammatory, DNA binding and chemosensing activities. In the present review, the above-mentioned activities of the nitrogen-containing heterocyclic compounds (pyridines), hydroxyl (phenols) and azo derivatives are discussed with reference to the minimum inhibitory concentration and structure–activity relationship, which clearly indicate that the presence of nitrogen in the phenyl ring; in addition, the hydroxyl substituent and the incorporation of a diazo group is crucial for the improved efficacies of the compounds in probing different diseases. The comparison was made with the reported drugs and new synthetic derivatives that showed recent therapeutic perspectives made in the last five years.

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One-pot, simple and efficient synthesis of novel bioactive 4-aryl-1,2-dihydro-6-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-oxopyridin-3-carbonitriles via multi-component approach

Cited by 11 publications

References 17 publications

Synthesis and Spectral Characterisation of (E)-3-(3-(4 (Dimethylamino)Phenyl)Acrylo-yl)-4-Hydroxy-2H-Chromen-2-One and Their Antibacterial Activity and Acetylcholinesterase Inhibition

Synthesis and Spectral Characterisation of (E)-3-(3-(4 (Dimethylamino)Phenyl)Acrylo-yl)-4-Hydroxy-2H-Chromen-2-One and Their Antibacterial Activity and Acetylcholinesterase Inhibition

Synthesis, characterization and in vitro bioactivity studies of isoindolin‐1‐3‐phosophonate compounds

Pyridine Scaffolds, Phenols and Derivatives of Azo Moiety: Current Therapeutic Perspectives

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