Multicomponent Synthesis of 2,4,5-Trisubstituted Thiazoles\nUsing a Sustainable Carbonaceous Catalyst and Assessment of Its Herbicidal\nand Antibacterial Potential

Herein, a novel, biocatalyzed, and\non-water microwave-assisted\nmulticomponent methodology have been developed for the synthesis of\ntrisubstituted thiazoles (<b>4a</b>–<b>4v</b>).\nThe reaction was catalyzed using a sulfonated peanut shell residue-derived\ncarbonaceous catalyst (<b>SPWB</b>). The developed catalyst\nwas characterized using Fourier transform infrared (FTIR), a Brunauer–Emmett–Teller\n(BET) surface area analyzer, a field emission scanning electron microscope\n(FE-SEM), energy-dispersive X-ray (EDX), and a particle size analyzer\n(PSA). The acidic sites have been established using acid–base\nback-titration methods. The molecular structures of all the synthesized\ncompounds were validated using FT-IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, elemental, and HRMS analyses. Herbicidal potential was evaluated\nby using Raphanus sativus L. as a model.\nFurthermore, the antibacterial potential of thiazoles was evaluated\nagainst Staphylococcus aureus, Bacillus subtilis, Xanthomonas campestris, Escherichia coli, Micrococcus luteus, and Pseudomonas\naeruginosa bacterial strains. The compound <b>4r</b> displayed improved seed growth inhibition in Raphanus\nsativus L. versus a commercially available herbicide, <i>i.e.,</i> pendimethalin. The antibacterial activity was promising\nagainst bacterial strains (MIC: 4–64 μg/mL). The compound <b>4r</b> was the most potent against P. aeruginosa and S. aureus (MIC: 0.0076 μM)\nversus standard drug streptomycin (MIC: 0.0138 μM). Moreover, <i>in silico</i> studies performed with the most effective compound <b>4r</b> against P. aeruginosa revealed\nits potential binding mode within the protein binding pocket. The\nbiological data revealed compound <b>4r</b> as a potential candidate\nfor the development of potent herbicidal and antibacterial agents.\nIn a nutshell, this study offers peanut shell biowaste to be a sustainable\nbiomass for heterogeneous acid catalyst preparation and its application\nin the multicomponent synthesis of bioactive thiazoles, accommodating\nthe concept of sustainable development goals and circular bioeconomy.

Publication Details

Journal
Figshare
Published
2024-12-04
DOI
https://doi.org/10.1021/acs.jafc.4c05293.s001
Primary Topic
Sunflower and Safflower Cultivation
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article
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article

Multicomponent Synthesis of 2,4,5-Trisubstituted Thiazoles\nUsing a Sustainable Carbonaceous Catalyst and Assessment of Its Herbicidal\nand Antibacterial Potential

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Sunflower and Safflower Cultivation
article

Multicomponent Synthesis of 2,4,5-Trisubstituted Thiazoles\nUsing a Sustainable Carbonaceous Catalyst and Assessment of Its Herbicidal\nand Antibacterial Potential

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Abstract

Herein, a novel, biocatalyzed, and\non-water microwave-assisted\nmulticomponent methodology have been developed for the synthesis of\ntrisubstituted thiazoles (<b>4a</b>–<b>4v</b>).\nThe reaction was catalyzed using a sulfonated peanut shell residue-derived\ncarbonaceous catalyst (<b>SPWB</b>). The developed catalyst\nwas characterized using Fourier transform infrared (FTIR), a Brunauer–Emmett–Teller\n(BET) surface area analyzer, a field emission scanning electron microscope\n(FE-SEM), energy-dispersive X-ray (EDX), and a particle size analyzer\n(PSA). The acidic sites have been established using acid–base\nback-titration methods. The molecular structures of all the synthesized\ncompounds were validated using FT-IR, <sup>1</sup>H NMR, <sup>13</sup>C NMR, elemental, and HRMS analyses. Herbicidal potential was evaluated\nby using Raphanus sativus L. as a model.\nFurthermore, the antibacterial potential of thiazoles was evaluated\nagainst Staphylococcus aureus, Bacillus subtilis, Xanthomonas campestris, Escherichia coli, Micrococcus luteus, and Pseudomonas\naeruginosa bacterial strains. The compound <b>4r</b> displayed improved seed growth inhibition in Raphanus\nsativus L. versus a commercially available herbicide, <i>i.e.,</i> pendimethalin. The antibacterial activity was promising\nagainst bacterial strains (MIC: 4–64 μg/mL). The compound <b>4r</b> was the most potent against P. aeruginosa and S. aureus (MIC: 0.0076 μM)\nversus standard drug streptomycin (MIC: 0.0138 μM). Moreover, <i>in silico</i> studies performed with the most effective compound <b>4r</b> against P. aeruginosa revealed\nits potential binding mode within the protein binding pocket. The\nbiological data revealed compound <b>4r</b> as a potential candidate\nfor the development of potent herbicidal and antibacterial agents.\nIn a nutshell, this study offers peanut shell biowaste to be a sustainable\nbiomass for heterogeneous acid catalyst preparation and its application\nin the multicomponent synthesis of bioactive thiazoles, accommodating\nthe concept of sustainable development goals and circular bioeconomy.

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