Microwave-assisted synthesis, antioxidant activity, docking simulation, and DFT analysis of different heterocyclic compounds

Abstract

In this investigation, pressure microwave irradiation was used to clarify the activity of 1-(2-hydroxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one (3) towards several active methylene derivatives utilized the pressurized microwave irradiation as green energy resource . Chalcone 3 was allowed to react with ethyl cyanoacetate, acetylacetone, and thioglycolic acid; respectively, at 70 °C with pressure under microwave reaction condition to afford the corresponding 2-hydroxyphenylcyanopyridone, 2-hydroxyphenyl acetylcyclohexanone, and thieno[2,3-c]chromen-4-one derivatives respectively. Moreover, the reaction of chalcone 3 with hydrogen peroxide with stirring affords the corresponding chromen-4-one derivative. All the synthesized compounds were confirmed through spectral tools such as FT-IR, 1HNMR, 13CNMR, and mass spectrum. Furthermore, the synthesized heterocycles were exhibited excellent antioxidant activity and comparable with vitamin C, where the presence of the OH group increases the scavenger radical inhibition. Furthermore, the biological activity of compound 12 was demonstrated through molecular docking stimulation using two proteins, PDBID: 1DH2 and PDBID: 3RP8, which showed that compound 12 possesses greater binding energy and a shorter bond length comparable with ascorbic acid. Also, the compounds were optimized through DFT/B3LYP/6-31G (d,p) basis set and identification of their physical descriptors, whereas the compound 12 was confirmed through X-Ray single structure with Hirsh field analysis of the compound to know the hydrogen electrostatic bond interaction, and correlated with the optimized structure by comparing their bond length, bond angle, FT-IR, and NMR, which gave excellent correlation.

Student perceptions of partial charges and nucleophilicity/electrophilicity when provided with either a bond-line, ball-and-stick, or electrostatic potential map for molecular representation

“…Practicing chemists generate EPMs from experimental data and use the resulting model to detect high reactivity within a molecule. Examples of this are included in the popular journal Nature in which several articles were published using EPMs during the year this paper was written (Jain et al, 2023;Kang et al, 2023;Shalaby et al, 2023). Being able to interpret and utilize EPMs is becoming an essential skill of a practicing chemist and should be considered as a part of student training.…”

Exploring the Antioxidant Potency of New Naphthalene‐Based Chalcone Derivatives: Design, Synthesis, Antioxidant Evaluation, Docking Study, DFT Calculations

“…To demonstrate the antioxidant potential of the newly synthesized compounds (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16), their radical-scavenging capacities were determined using the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) assay. [31] This method is based on the ability of the DPPH radical to abstract H-atoms from antioxidants (AÀ H) to form the hydrazine derivative DPPHÀ H Figure 1, as depicted in reaction 1.…”

“…A wide range of pharmacological applications has been reported for chalcone derivatives incorporating a heterocyclic scaffold, which includes antioxidant, antibacterial, anticancer, antiplatelet, and anti-inflammatory activities. [6][7][8][9][10][11] Among these properties, the antioxidant properties of chalcone derivatives have been extensively investigated. [12] It is reported that chalcones with proper functional substituents (e. g., OH or NH) can exhibit a great efficacy in antioxidant activity due to their potent abilities to scavenge ROS directly through hydrogen or electron transfer.…”

Copper Catalyzed Synthesis of Heterocyclic Molecules via C–N and C–O Bond Formation under Microwaves: A Mini-Review

“…Starting from heterocyclic synthesis, metal-mediated chemistry, and industrial preparation of aromatic compounds using microwaves, this technology has been extended to continuous-flow organic synthesis also. Lastly the wide application of microwaves in organic synthesis can enhance its value for the synthesis of high-value organic chemicals, polymers, and nanomaterials in much less time than would be required using conventional heating methods . Recently, Szostak and his group reviewed the synthesis of privileged heterocyclic moieties which could be amenable to microwave irradiation also …”