

An up-to-date short review of the chalcone methodologies is presented, which is the most
interesting and beneficial for choosing the desired protocol to synthesize suitable derivatives of chalcones.
Chalcones are fluorescent, stable compounds which contribute to the synthesis of various
pharmacologically important heterocyclic structure-based derivatives. Chalcone has displayed a remarkable
curative efficiency to cure several diseases. Several schemes and methodologies have been
reported for employing different catalysts and reagents. The development of improved methodologies
of α, β-unsaturated carbonyl compounds is still on going. In this review, synthetic methodologies
and their recent modification in designing new methods with efficient, economical, eco-friendly
and high yield are discussed.


Recent Synthetic Methodologies for Chalcone Synthesis (2013-2018)

Synthesis, spectroscopic characterization and antibacterial evaluation by chalcones derived of acetophenone isolated from Croton anisodontus Müll.Arg.

Targeted cancer therapy has become a high potential cancer treatment. Epidermal growth factor receptor (EGFR), which plays an important role in cell signaling, enhanced cell survival and proliferation, has been suggested as molecular target for the development of novel cancer therapeutics. In this study, a series of chalcone derivatives was screened by in vitro cytotoxicity against the wild type (A431 and A549) and mutant EGFR (H1975 and H1650) cancer cell lines, and, subsequently, tested for EGFR-tyrosine kinase (TK) inhibition. From the experimental screening, all chalcones seemed to be more active against the A431 than the A549 cell line, with chalcones 1c, 2a, 3e, 4e, and 4t showing a more than 50% inhibitory activity against the EGFR-TK activity and a high cytotoxicity with IC50 values of < 10 µM against A431 cells. Moreover, these five chalcones showed more potent on H1975 (T790M/L858R mutation) than H1650 (exon 19 deletion E746-A750) cell lines. Only three chalcones (1c, 2a and 3e) had an inhibitory activity against EGFR-TK with a relative inhibition percentage that was close to the approved drug, erlotinib. Molecular dynamics studies on their complexes with EGFR-TK domain in aqueous solution affirmed that they were well-occupied within the ATP binding site and strongly interacted with seven hydrophobic residues, including the important hinge region residue M793. From the above information, as well as ADMET (absorption, distribution, metabolism, excretion, and toxicity) properties, all three chalcones could serve as lead compounds for the development of EGFR-TK inhibitors.

https://www.mdpi.com/1420-3049/24/6/1092/pdf

Biological Evaluation and Molecular Dynamics Simulation of Chalcone Derivatives as Epidermal Growth Factor-Tyrosine Kinase Inhibitors

Combined 3D-QSAR and docking analysis for the design and synthesis of chalcones as potent and selective monoamine oxidase B inhibitors.

Background: Chalcones are part of a family of small phenolic compounds that are being extensively studied for presenting a diversity of molecular structures and biological activities. In this paper, two chalcones, (E)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one (1), (E)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one (2), were synthesized by Claisen–Schmidt condensation. Methods: The molecular structures of these chalcones were determined by Nuclear Magnetic Resonance and characterized by infrared, Raman spectroscopy, and electrochemical analysis at room temperature. Vibrational wavenumbers were predicted using Functional Density Theory (DFT) calculations, and their normal modes were analyzed in terms of potential energy distribution (PED). Besides this, DFT calculations were performed to obtain the molecular orbitals and their quantum descriptors. The UV-Vis absorption spectrum of the synthesized chalcones was measured and compared with each other. In addition, analyses of antimicrobial activity and modulation of antibiotic resistance were carried out to assess the antibacterial potential of these chalcones. Results: The vibrational spectra of polycrystalline chalcones obtained by ATR-FTIR, FT-Raman and DFT calculations allowed a complete assignment of the vibrational modes, and revealed the quantum chemical parameters. Both chalcones did not show good responses when associated with the antibiotics Ciprofloxacin and Cephalexin against S. aureus 10 and E. coli 06 strains. However, a significant potentiating of the Gentamicin activity against S. aureus 10 and E. col 06 strains was observed for chalcone 2. On the other hand, when associated with Norfloxacin, an antagonistic effect was observed. The results found for EtBr suggest that, although the tested chalcones behave as efflux pump inhibitors, probably inhibiting other efflux pumps, they were not able to inhibit NorA. Thus, these synthetic chalcones are not recommended for use in association with Norfloxacin against strains of S. aureus 1199-B that overexpress the NorA gene. Conclusions: Spectroscopic data confirmed the structure of the chalcones, and chalcone 2 showed potential as an adjuvant in antibiotic therapy.

Structural, Vibrational and Electrochemical Analysis and Antibacterial Potential of Isomeric Chalcones Derived from Natural Acetophenone

Chalcones are a valuable molecule of medicinal importance due to presence of reactive ketoethylenic group –CO–CH=CH–, belonging to the flavonoid family These reactive α,β-unsatutated keto function in chalcones are  responsible for their biological activity Chalcone can be synthesized by several methods using aldehydes and ketones as starting material This review is focused about different methods of synthesis and versatile biological activity of chalcones including antimicrobial, anticancer, antioxidant, antimalarial, antituberculosis etc

A Review on Chalcones Synthesis and their Biological Activity

8-Aryl-3-(β-D-glucopyranosyl)-4-oxo-4H,5H-1,2,4-triazolo-[4,3b]-1,4,2,6-dithiadiazine-1,1-dioxides 4 have been conveniently prepared from 8-aryl-4-oxo-4H,5H-1,2,4-triazolo-[4,3-b]-1,4,2,6dithiadiazine-1,1-dioxides 2 by reaction of β-D-1,2,3,4,6-penta-Oacetylglucopyranose and iodine. Compounds 2 are synthesized by reported methods from 3-mercapto-5-aryl-1,2,4-triazole 1, chlorosulphonyl isocyanate and N-di-isopropyl-ethylamine in acetonitrile. All compounds have been tested in vitro for their antifungal activity against three fungal species Cephalosporium saccharii, Colletotrichum falcatum and Helminthosporium oryzae.

http://nopr.niscair.res.in/bitstream/123456789/31494/1/IJCB%2054B%285%29%20682-686.pdf

Shipra Verma

Papers

A Review on Chalcones Synthesis and their Biological Activity

Synthesis and fungicidal activity of some 8-aryl-3-( -D-glucopyranosyl)-4-oxo-4 H ,5 H -1,2,4-triazolo-[4,3- b ]-1,4,2,6-dithiadiazine-1,1-dioxides

Synthesis and Biological Evaluation of Pyrimidin-2-yl)-[1,2,4]triazolo[4,3-a]pyrimidin-3-yl)oxazole Derivatives as Anticancer agents