Eco-friendly Cu/NiO nanoparticle synthesis: Catalytic potential in isatin-based chalcone synthesis for anticancer activity.

Isatin (1H-indole-2,3­dione) is a natural heterocyclic compound extracted from various plants and has biological activity as an anticancer agent. Chalcones with the addition of several functional groups (hydroxyl, carboxyl, phenyl, etc.) may become useful templates for the development of new anticancer agents. In this study, we have synthesized Cu/NiO nanoparticles using the sol-gel method involving annona muricata L leaf extract and used as catalysts for the synthesis of isatin-based chalcone. These compounds will be applied as anticancer agents against MCF-7 cancer cell. According to the characterization results using FT-IR, XRD, FESEM-EDS, the crystal size for Cu/NiO nanoparticles was 5.4566 nm and the particle size was 25.081 ± 8.422 nm with irregular spherical shapes. The synthesis of isatin based on chalcone using the reflux method refers to the claisen schmidt condensation reaction using 5% mmol Cu/NiO nanoparticles resulting in yields for each product of 50 % (product 1), 32.37 % (product 2), 24.29 % (product 3), 32.35 % (product 4), 50.86 % (product 5), and 69.88 % (product 6). The effectiveness of the six products against MCF-7 cancer cells can be seen from the IC50 values as follows product 1 (IC50 = 0.00157 µg/ml), product 2 (IC50 = 100.897 µg/ml), product 3 (IC50 = 81.991 µg/ml), product 4 (IC50 = 8107.54 µg/ml), product 5 (IC50 = 77.9291 µg/ml), product 6 (IC50 = 25.4521 µg/ml). Based on the IC50 value obtained, it shows that product 1 and product 6 have strong activity when compared to another product on against MCF-7 cancer cells. •Acetophenone as a simple ketone was modified to 2-acetylpyridine.•Modification was performed adding Cu/NiO nanoparticle as catalyst.•Final products exhibited anticancer activity (MCF-7).

Synthesis of camphor thiazole derivates from Dryobalanops aromatica and its bioactivity as antioxidants and antidiabetes against alpha glucosidase enzymes.

Camphor is synthesized from the Sumatran camphor plant (Dryobalanops aromatica) in previous experiments. It can be synthesized with thiosemicarbazide, ethy-2­chloro acetoacetate, and sodium acetate (catalyze) to form camphor derivate with thiazole ring structure. Hydrazine and phenylhydrazine were both used to make the thiazole ring variations. All the compounds were purified by recrystallization method and characterized by TLC, FTIR, UV-vis, and LC-MS. Camphor thiazole (Product 1), camphor thiazole hydrazine (Product 2), and camphor thiazole phenylhydrazine (Product 3) were successfully synthesized with%yields of 73.24 %; 77.36 %; and 72.91 % respectively. Furthermore, their antioxidant activity was measured using the DPPH free radical method. Product 2 had the strongest antioxidant activity with IC50 value of 6.93 ppm. The antidiabetic activity was measured using the α-glucosidase enzyme. This indicated that product 1 had the best inhibitory activity against the α-glucosidase enzyme with IC50 values of 869.06 ppm.•We developed an alternative method to utilize camphor extracted from the D. aromatica plant to be used as an alternative medicinal ingredient related to antioxidants and antidiabetes.•All products were successfully synthesized and have the potential to be used as antioxidants with an IC50 value of 6.93 ppm for Product 2 and as antidiabetics by means of an α-glucosidase inhibitor with an IC50 value of 869.06 ppm for Product 1.

Preparation of azachalcone derivatives vial-proline/ Et3N-catalyzed aldol condensation and study of their antioxidant potential.

Chalcones, with two connected aromatic rings through an α,ß-unsaturated carbonyl skeleton, display diverse biological roles like antimalarial, antibacterial, anticancer, and antioxidant activities. This research focuses on crafting azachalcone derivatives from 2-acetylpyridine and aromatic aldehydes using l-proline/Et3N as a catalyst. Refinements encompass catalyst dosage, solvents, temperature, and post-reaction treatments. The optimized approach employs l-proline (0.15 equiv.)/ Et3N (0.30 equiv.) at room temperature in methanol. Derivatives are successfully synthesized in moderate to favorable yields, akin to sodium hydroxide as the benchmark catalyst. Notably, antioxidant assessment via the DPPH method spotlights compound 2b and 2d (100 ppm concentration), showcasing significant antioxidant potency with inhibition percentages of 92.22 % and 74.41 %, respectively.•l-proline/ Et3N is successful to use in aldol condensation reaction.•Azachalcones based 2-acetylpyridine were successfully synthesized using the catalyst.•Azachalcones showed antioxidant activity against DPPH radical.

A convenient method for the construction of triazole-bonded chalcone derivatives from acetophenone: Synthesis and free radical scavenging investigation.

The substituted 1,2,3-triazole core is prevalent in numerous commercially available drugs utilized for a wide range of clinical applications. Simultaneously, chalcone represents a privileged framework discovered in natural products exhibiting intriguing bioactivities. In this study, we synthesized triazole-bonded chalcone compounds (4ax-4by), starting from a simple aromatic ketone, acetophenone, which underwent aldol condensation to give hydroxychalcone intermediate. In the second step, the hydroxyl group of chalcone compound was adducted with propargyl moiety through propargylation reaction. Then, the propargylated products underwent smooth copper-mediated azide-alkyne cyclization to give the triazole-bonded chalcones as the final products. They were characterized by IR, NMR and HRMS, and evaluated their radical scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH). Among the tested products, compound 4by was denoted as the most potent derivative which can inhibit DPPH radical in 91.62 ± 0.10% at 500 ppm.•Acetophenone as a simple ketone was modified to triazole-bonded chalcones.•Modification was performed through three steps reaction.•Final products exhibited free radical scavenging activity.

Synthesis of antioxidant and antimicrobial bioactive compounds based on the quinoline-hydrazone and benzimidazole structure.

Quinoline and its derivatives are known to have various biological activities such as antibacterial and antioxidant. Therefore, this study aims to synthesize quinoline moiety from isatin and ethyl acetoacetate by Pfitzinger reaction under acidic conditions. The benzimidazole derivative was synthesized from quinoline and o-phenylenediamine by a solvent-less reaction, while the hydrazone derivative was formed by the reaction with hydrazine hydrate and aromatic aldehyde. In addition, 4-hydroxybenzaldehyde was used as an aromatic aldehyde. The four compounds formed were characterized by thin-layer chromatography (TLC), melting point measurement, Fourier-transform infrared, liquid chromatography-mass spectrometry, and ultraviolet-visible spectrophotometry. They were also evaluated for their antioxidant and antimicrobial activities using the 2,2-diphenyl-1-picrylhydrazyl assay and the disc diffusion method, respectively. All compounds showed weak antioxidant activity compared to ascorbic acid; the quinoline-hydrazone derivative showed the best antioxidant activity with IC50 = 843.52 ppm, while the IC50 value for quinoline-benzimidazole was 4784.66 ppm. All synthesized compounds have not been confirmed to be effective against Staphylococcus aureus and Escherichia coli bacteria in a concentration range of 75-1000 ppm. The bioactive compounds based on the quinoline-hydrazone and benzimidazole structures have been successfully synthesized and tested for their activity as antioxidant and antimicrobial agents.

Synthesis, α-Glucosidase Inhibitory Activity and Molecular Docking Study of Chalcone Derivatives Bearing a 1H-1,2,3-Triazole Unit.

Diabetes mellitus (DM) is a metabolic condition that is a major health concern around the world. The current study investigates the synthesis of a series of chalcone and 1H-1,2,3-triazole hybrid compounds and their in vitro inhibitory potential against α-glucosidase. The antidiabetic analysis revealed that compounds 4a and 4b are highly active agents with IC50 of 3.90 and 4.77 µM, respectively. These results are close to quercetin (IC50 = 4.24 µM) as the reference standard. Molecular docking study strongly supports the active interaction of the 4a and 4b to the enzyme through cation-π interaction and hydrogen bonding between the ligands and the active site of Saccharomyces cerevisiae α-glucosidase enzyme. This study broadened the potential of designing chalcone-triazole hybrid compounds as antidiabetic drug candidates in the pharmaceutical sector.