{"title":"可持续碳质催化剂多组分合成2,4,5-三取代噻唑及其除草抑菌潜力评价","authors":"Shweta, Sandhya Chahal, Rahul Kumar Dhaka, Anuj Rana, Gaurav Joshi, Rajvir Singh, Snigdha Singh, Devender Singh, Parvin Kumar, Jayant Sindhu","doi":"10.1021/acs.jafc.4c05293","DOIUrl":null,"url":null,"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.","PeriodicalId":41,"journal":{"name":"Journal of Agricultural and Food Chemistry","volume":"65 1","pages":""},"PeriodicalIF":6.2000,"publicationDate":"2024-12-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Multicomponent Synthesis of 2,4,5-Trisubstituted Thiazoles Using a Sustainable Carbonaceous Catalyst and Assessment of Its Herbicidal and Antibacterial Potential\",\"authors\":\"Shweta, Sandhya Chahal, Rahul Kumar Dhaka, Anuj Rana, Gaurav Joshi, Rajvir Singh, Snigdha Singh, Devender Singh, Parvin Kumar, Jayant Sindhu\",\"doi\":\"10.1021/acs.jafc.4c05293\",\"DOIUrl\":null,\"url\":null,\"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.\",\"PeriodicalId\":41,\"journal\":{\"name\":\"Journal of Agricultural and Food Chemistry\",\"volume\":\"65 1\",\"pages\":\"\"},\"PeriodicalIF\":6.2000,\"publicationDate\":\"2024-12-04\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Agricultural and Food Chemistry\",\"FirstCategoryId\":\"97\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.jafc.4c05293\",\"RegionNum\":1,\"RegionCategory\":\"农林科学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"AGRICULTURE, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Agricultural and Food Chemistry","FirstCategoryId":"97","ListUrlMain":"https://doi.org/10.1021/acs.jafc.4c05293","RegionNum":1,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"AGRICULTURE, MULTIDISCIPLINARY","Score":null,"Total":0}
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 (4a–4v). The reaction was catalyzed using a sulfonated peanut shell residue-derived carbonaceous catalyst (SPWB). 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, 1H NMR, 13C NMR, elemental, and HRMS analyses. Herbicidal potential was evaluated by using Raphanus sativus L. as a model. Furthermore, the antibacterial potential of thiazoles was evaluated against Staphylococcus aureus, Bacillus subtilis, Xanthomonas campestris, Escherichia coli, Micrococcus luteus, and Pseudomonas aeruginosa bacterial strains. The compound 4r displayed improved seed growth inhibition in Raphanus sativus L. versus a commercially available herbicide, i.e., pendimethalin. The antibacterial activity was promising against bacterial strains (MIC: 4–64 μg/mL). The compound 4r was the most potent against P. aeruginosa and S. aureus (MIC: 0.0076 μM) versus standard drug streptomycin (MIC: 0.0138 μM). Moreover, in silico studies performed with the most effective compound 4r against P. aeruginosa revealed its potential binding mode within the protein binding pocket. The biological data revealed compound 4r 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.
期刊介绍:
The Journal of Agricultural and Food Chemistry publishes high-quality, cutting edge original research representing complete studies and research advances dealing with the chemistry and biochemistry of agriculture and food. The Journal also encourages papers with chemistry and/or biochemistry as a major component combined with biological/sensory/nutritional/toxicological evaluation related to agriculture and/or food.