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.
Authors
- Gaurav Joshi (ORCID: https://orcid.org/0000-0002-7812-2871)
- Jayant Sindhu (ORCID: https://orcid.org/0000-0003-0207-0662)
- Sandhya Chahal (ORCID: https://orcid.org/0000-0002-0092-9659)
- Snigdha Singh (ORCID: https://orcid.org/0000-0003-0319-8887)
- Parvin Kumar (ORCID: https://orcid.org/0000-0002-2635-6465)
- Anuj Rana
- Devender Singh (ORCID: https://orcid.org/0000-0002-2180-5049)
- Rahul Kumar (ORCID: https://orcid.org/0000-0001-5451-8030)
- Rajvir Singh (ORCID: https://orcid.org/0000-0002-2826-0205)
- Shweta Shweta
Institutions
- University of Delhi (IN)
- Kurukshetra University (IN)
- Hemwati Nandan Bahuguna Garhwal University (IN)
- Chaudhary Charan Singh Haryana Agricultural University (IN)
- Maharshi Dayanand University (IN)
Publication Details
- 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
Funders
- Department of Science and Technology, Ministry of Science and Technology, India
- Uttarakhand State Council for Science and Technology