Design, synthesis, and fungicidal evaluation of a series of novel 5-methyl-1H-1,2,3-trizole-4-carboxyl amide and ester analogues

Wang, Zhenjun; Gao, Yang; Hou, Yan-Ling; Zhang, Cheng; Shibata, Yu; Bian, Qiang; Li, Zhengming; Zhao, Wei‐Guang

doi:10.1016/j.ejmech.2014.08.029

Cited by 54 publications

(24 citation statements)

References 34 publications

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“…1,2,3-Triazoles are an important class of heterocyclic compounds due to their wide usage as synthetic intermediates and pharmaceuticals [1][2][3]. Many triazole derivatives are found to exhibit various pharmacological properties such as antimicrobial [4], antiepileptic [5], antitubercular [6], and antibacterial [7], and a large number of 1,2,3-triazoles have also been reported with significant anticancer activities [8][9][10]. Since they are nontoxic, highly stable compounds and mostly water soluble, the 1,2,3-triazole derivatives could be ideal drug candidate and they could participate actively in molecular interactions by hydrogen bond formation [11] which implies their facility to binding with the biological targets [12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Antibacterial Activity of Diethyl 1-((4-Methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylate

Boukhssas

Aouine

Faraj

et al. 2017

Journal of Chemistry

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The compound, diethyl 1-((4-methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylate 2, was synthesized in high yield, through 1,3-dipolar cycloaddition reaction of 4-(azidomethyl)-4-methyl-2-phenyl-4,5-dihydrooxazole and diethyl but-2-ynedioate in the absence of a solvent. The structure of the synthesized compound was established on the basis of NMR spectroscopy ( 1 H, 13 C), X-ray crystallography, and MS data. The prepared compound was also tested in vitro for its antibacterial activity against Gram-positive bacteria (Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli). The calculation of MBC/MIC ratio showed that this triazole derivative 2 had a bactericidal effect on the two strains tested.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Antibacterial Activity of Diethyl 1-((4-Methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylate

Boukhssas

Aouine

Faraj

et al. 2017

Journal of Chemistry

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“…Thiazole-containing aromatic heterocycles are reported to bind to certain proteins and receptors of bacteria and exhibit a wide range of biological activities such as insecticidal [4,5], bactericidal [6][7][8], herbicidal [9], antiviral [10] and fungicidal ones [11,12]. In addition, compounds with an amide structure have revealed various activities as antimicrobial [13][14][15] and nematicidal [16,17] agents. Based on the reported good performance of derivatives containing thiazole or amide groups, splicing them to get new antibacterial structures was presumed to be a reasonable and promising approach.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Evaluation of N-phenylacetamide Derivatives Containing 4-Arylthiazole Moieties

Zhou

Wang

et al. 2020

Molecules

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A series of new N-phenylacetamide derivatives containing 4-arylthiazole moieties was designed and synthesized by introducing the thiazole moiety into the amide scaffold. The structures of the target compounds were confirmed by 1H-NMR, 13C-NMR and HRMS. Their in vitro antibacterial activities were evaluated against three kinds of bacteria—Xanthomonas oryzae pv. Oryzae (Xoo), Xanthomonas axonopodis pv. Citri (Xac) and X.oryzae pv. oryzicola (Xoc)—showing promising results. The minimum 50% effective concentration (EC50) value of N-(4-((4-(4-fluoro-phenyl)thiazol-2-yl)amino)phenyl)acetamide (A1) is 156.7 µM, which is superior to bismerthiazol (230.5 µM) and thiodiazole copper (545.2 µM). A scanning electron microscopy (SEM) investigation has confirmed that compound A1 could cause cell membrane rupture of Xoo. In addition, the nematicidal activity of the compounds against Meloidogyne incognita (M. incognita) was also tested, and compound A23 displayed excellent nematicidal activity, with mortality of 100% and 53.2% at 500 μg/mL and 100 μg/mL after 24 h of treatment, respectively. The preliminary structure-activity relationship (SAR) studies of these compounds are also briefly described. These results demonstrated that phenylacetamide derivatives may be considered as potential leads in the design of antibacterial agents.

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“…However, with the frequent and extensive application of these aromatic amide fungicides, several resistant fungi have been reported [ 10 , 11 , 12 ]. Therefore, it is necessary to develop new fungicides with novel molecular frameworks to effectively control plant diseases [ 13 , 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel Benodanil-Heterocyclic Carboxamide Hybrids as a Potential Succinate Dehydrogenase Inhibitors

et al. 2020

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In order to discover new antifungal agents, twenty novel benodanil-heterocyclic carboxamide hybrids were designed, synthesized, and characterized by 1H NMR and HRMS. In vitro, their antifungal activities against four phytopathogenic fungi were evaluated, as well as some of the target compounds at 50 mg/L demonstrated significant antifungal activities against Rhizoctonia solani. Especially, compounds 17 (EC50 = 6.32 mg/L) and 18 (EC50 = 6.06 mg/L) exhibited good antifungal activities against R. solani and were superior to the lead fungicide benodanil (a succinate dehydrogenase inhibitor, SDHI) (EC50 = 6.38 mg/L). Furthermore, scanning electron microscopy images showed that the mycelia on treated media with the addition of compound 17 grew abnormally as compared with the negative control with tenuous, wizened, and overlapping colonies, and compounds 17 (IC50 = 52.58 mg/L) and 18 (IC50 = 56.86 mg/L) showed better inhibition abilities against succinate dehydrogenase (SDH) than benodanil (IC50 = 62.02 mg/L). Molecular docking revealed that compound 17 fit in the gap composed of subunit B, C, and D of SDH. Furthermore, it was shown that the main interaction, one hydrogen bond interaction, was observed between compound 17 and the residue C/Trp-73. These studies suggested that compound 17 could act as a potential fungicide to be used for further optimization.

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Design, synthesis, and fungicidal evaluation of a series of novel 5-methyl-1H-1,2,3-trizole-4-carboxyl amide and ester analogues

Cited by 54 publications

References 34 publications

Synthesis, Characterization, and Antibacterial Activity of Diethyl 1-((4-Methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylate

Synthesis, Characterization, and Antibacterial Activity of Diethyl 1-((4-Methyl-2-phenyl-4,5-dihydrooxazol-4-yl)methyl)-1H-1,2,3-triazole-4,5-dicarboxylate

Synthesis and Antibacterial Evaluation of N-phenylacetamide Derivatives Containing 4-Arylthiazole Moieties

Synthesis and Biological Evaluation of Novel Benodanil-Heterocyclic Carboxamide Hybrids as a Potential Succinate Dehydrogenase Inhibitors

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