Abstract
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.
Highlights
Coumarins are an important class of benzopyrones present in various natural products and numerous pharmaceutically valuable compounds [1]
We report the synthesis, characterisation, and bioactivity of a new (E)-3-(3-(4-(dimethylamino) phenyl) acrylo-yl)-4-hydroxy-2H-chromen-2-one (3). e design of our novel coumarin benefits from the bioactivities of both the coumarin and chalcone moieties and simultaneously exploits the ability of the chalcone moiety to serve as a built-in probe for microenvironment probing. ese chalcone properties allowed us to assess the nature of the interaction between our developed coumarin and DNA molecules. e application of this coumarin as a new, potential DNA fluorescent stain is described
E IR spectrum of compound 1 revealed a strong band at 3185 cm−1, confirming the presence of an OH group and a band at 1700 cm−1, which is characteristic of the coumarin C O moiety. e 1 H NMR data of 1 revealed a signal at 2.72 ppm attributed to the methyl protons, and the aromatic protons resonated between 7.1 and 7.98 ppm. e hydroxyl proton (OH) resonated at 17.69 ppm
Summary
Coumarins are an important class of benzopyrones present in various natural products and numerous pharmaceutically valuable compounds [1] With their privileged scaffold, coumarins exhibit a broad spectrum of biological activity; namely, they act as anticoagulants, antibiotics, and antioxidants, as well as anti-inflammatory, anti-HIV, and anticancer agents. Novobiocin and clorobiocin are coumarin-derived antibiotics that are used as competitive inhibitors of the bacterial adenosine-5-triphosphate (ATP)-binding gyrase B subunit where the inhibition they provide blocks the negative supercoiling of relaxed DNA [5,6,7]. Another example is wedelolactone, a natural, coumarin-containing product that. We report the synthesis, characterisation, and bioactivity of a new (E)-3-(3-(4-(dimethylamino) phenyl) acrylo-yl)-4-hydroxy-2H-chromen-2-one (3). e design of our novel coumarin benefits from the bioactivities of both the coumarin and chalcone moieties and simultaneously exploits the ability of the chalcone moiety to serve as a built-in probe for microenvironment probing. ese chalcone properties allowed us to assess the nature of the interaction between our developed coumarin and DNA molecules. e application of this coumarin as a new, potential DNA fluorescent stain is described
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