Synthesis and Fungicidal Evaluation of Novel <i>β</i>-Carboline-Benzimidazole and <i>β</i>-Carboline-Benzothiazole Hybrids

霍新玉,; 李文斌,; 张博雅,; 陈晓飞,; 周月婷,; 张洁,; 韩小强,; 代斌,

doi:10.6023/cjoc201805053

Cited by 10 publications

(3 citation statements)

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“…The preparation of intermediates 1-methyl-9-substituted-β-carbolines ( 1a – h ) and 9-substituted-β-carboline-1-carboxaldehydes ( 2a – h ) has already been described in our previous reports. 41–44…”

Section: Methodsmentioning

confidence: 99%

New β-carboline derivatives containing imidazolium as potential VEGFR2 inhibitors: synthesis, X-ray structure, antiproliferative evaluations, and molecular modeling

Li¹,

Chen

Zhu

et al. 2022

RSC Med. Chem.

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Section: Methodsmentioning

confidence: 99%

New β-carboline derivatives containing imidazolium as potential VEGFR2 inhibitors: synthesis, X-ray structure, antiproliferative evaluations, and molecular modeling

Li¹,

Chen

Zhu

et al. 2022

RSC Med. Chem.

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“…At the concentration of 10 mg/L, the average inhibitory zone diameter of compound 43 against Aspergillus oryzae (A. oryzae) was 0.81 mm. However, the replacement of chlorine atoms with nitro groups had no significant effect on the fungicidal activity of compounds; for example, the average diameter of the inhibition zone of compound 44 against A. oryzae was 0.81 mm [ 84 ]. At the concentration of 50 mg/L, the inhibitory activities of compounds 45 and 46 against Rape sclerotinia rot were 80.08% and 81.61%, respectively [ 85 ].…”

Section: Antifungal Activitymentioning

confidence: 99%

Research Progress of Benzothiazole and Benzoxazole Derivatives in the Discovery of Agricultural Chemicals

Zou

Zhang

Xing

et al. 2023

IJMS

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Benzoxazole and benzothiazole have a broad spectrum of agricultural biological activities, such as antibacterial, antiviral, and herbicidal activities, which are important fused heterocyclic scaffold structures in agrochemical discovery. In recent years, great progress has been made in the research of benzoxazoles and benzothiazoles, especially in the development of herbicides and insecticides. With the widespread use of benzoxazoles and benzothiazoles, there may be more new products containing benzoxazoles and benzothiazoles in the future. We systematically reviewed the application of benzoxazoles and benzothiazoles in discovering new agrochemicals in the past two decades and summarized the antibacterial, fungicidal, antiviral, herbicidal, and insecticidal activities of the active compounds. We also discussed the structural–activity relationship and mechanism of the active compounds. This work aims to provide inspiration and ideas for the discovery of new agrochemicals based on benzoxazole and benzothiazole.

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“…For example, Huo et al synthesized (9-ethyl-⊎-carbolinyl)-2-benzimidazole, which presented high activity against rape scherotinia rot with 91.95% inhibition at 50 μg mL −1 . 8…”

Section: Introductionmentioning

confidence: 99%

Synthesis and fungicidal activity of novel benzimidazole derivatives bearing pyrimidine‐thioether moiety against Botrytis cinerea

Sun

Zhang

Qian

et al. 2021

Pest Management Science

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BACKGROUND: Botrytis cinerea is a serious plant fungus and strongly affects the yield and quality of crops. The main control strategy is the employment of fungicides. To research for efficient fungicide with novel structure, a series of novel benzimidazole derivatives bearing pyrimidine and thioether moieties were designed and synthesized.RESULTS: Some target compounds such as 4h, 4i, 4k, 4l, 4m, 4s, 4t and 4u exhibited notable fungicidal activities, with half maximal effective concentration (EC 50 ) values in the range 0.13-0.24 ∼g mL −1 , which means that their activities were comparable or higher than that of carbendazim (EC 50 = 0.21 ∼g mL −1 ). Among them, N-(4-fluorophenyl)-2-((4-(1H-benzimidazol-2-yl)-6-(4-methoxyphenyl) pyrimidin-2-yl)thio)acetamide (4m) displayed the best activity (EC 50 = 0.13 ∼g mL −1 ). Molecular electrostatic potential analysis of 4m elucidated that the NH moiety of benzimidazole ring was located in the positive potential region and may generate hydrogen bond with target amino acid residue. Molecular docking analysis revealed that there was one hydrogen bond and one π-π interaction between 4m and target protein.CONCLUSIONS: This study demonstrated that the benzimidazole derivatives bearing pyrimidine and thioether moieties can be further optimized as a lead compound for the control of B. cinerea. The combination of molecular electrostatic potential and molecular docking analyses may provide a valuable reference for studying the interaction between the ligand and target protein.

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Synthesis and Fungicidal Evaluation of Novel β-Carboline-Benzimidazole and β-Carboline-Benzothiazole Hybrids

Cited by 10 publications

References 0 publications

New β-carboline derivatives containing imidazolium as potential VEGFR2 inhibitors: synthesis, X-ray structure, antiproliferative evaluations, and molecular modeling

New β-carboline derivatives containing imidazolium as potential VEGFR2 inhibitors: synthesis, X-ray structure, antiproliferative evaluations, and molecular modeling

Research Progress of Benzothiazole and Benzoxazole Derivatives in the Discovery of Agricultural Chemicals

Synthesis and fungicidal activity of novel benzimidazole derivatives bearing pyrimidine‐thioether moiety against Botrytis cinerea

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