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

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

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Journal
Journal of Agricultural and Food Chemistry
Published
2024-12-04
DOI
https://doi.org/10.1021/acs.jafc.4c05293
Citations
3
Primary Topic
Multicomponent Synthesis of Heterocycles
Type
article
Field-Weighted Citation Impact
0.75

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article

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

Gaurav Joshi, Jayant Sindhu, Sandhya Chahal, Snigdha Singh et al.
3 citations
Journal of Agricultural and Food Chemistry
Multicomponent Synthesis of Heterocycles
0.75
article

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

Gaurav Joshi, Jayant Sindhu, Sandhya Chahal, Snigdha Singh, Parvin Kumar, Anuj Rana, Devender Singh, Rahul Kumar, Rajvir Singh, Shweta Shweta
article en
3 citations

Abstract

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

Journal of Agricultural and Food ChemistryVol. 72(50)
University of Delhi (IN), Kurukshetra University (IN), Hemwati Nandan Bahuguna Garhwal University (IN), Chaudhary Charan Singh Haryana Agricultural University (IN), Maharshi Dayanand University (IN)
Department of Science and Technology, Ministry of Science and Technology, India, Uttarakhand State Council for Science and Technology
Responsible consumption and production
Openalex Percentile: Top 31%
Multicomponent Synthesis of Heterocycles
0.75
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