Design, Synthesis, and Antifungal Activity of Novel Aryl-1,2,3-Triazole-β-Carboline Hybrids
| Autor: | Guo Liang, Xiaoqiang Han, Yueting Zhou, Xin-Yu Huo, Bin Dai, Xiaofei Chen, Jie Zhang |
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| Rok vydání: | 2018 |
| Předmět: |
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2 3-Triazole Antifungal Agents Proton Magnetic Resonance Spectroscopy β-carboline Pharmaceutical Science Microbial Sensitivity Tests 010402 general chemistry 01 natural sciences Article Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound Structure-Activity Relationship lcsh:Organic chemistry Drug Discovery Fusarium oxysporum Organic chemistry 1 2 3-trizole Physical and Theoretical Chemistry Carbon-13 Magnetic Resonance Spectroscopy Botrytis cinerea biology 010405 organic chemistry Organic Chemistry antifungal activity Fungi Triazoles biology.organism_classification Cycloaddition 0104 chemical sciences chemistry Chemistry (miscellaneous) Spectrometry Mass Matrix-Assisted Laser Desorption-Ionization Click chemistry Molecular Medicine Sodium azide Click Chemistry structure–activity relationships Azide Sclerotinia Carbolines |
| Zdroj: | Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry Molecules Volume 23 Issue 6 Molecules, Vol 23, Iss 6, p 1344 (2018) |
| ISSN: | 1420-3049 |
| Popis: | The copper catalytic azide and terminal alkyne cycloaddition reaction, namely &ldquo click chemistry&rdquo gives a new and convenient way to create l,4-disubstitutd-l,2,3-triazoles. In this work, 2-pyrrolecarbaldiminato&ndash Cu(II) complexes were established as efficient catalysts for the three-component 1,3-dipolar cycloaddition reaction of arylboronic acid and sodium azide (NaN3) with terminal alkynes in ethanol at room temperature to 50 ° C, 1,4-disubstituted 1,2,3-triazoles were synthesized. Following the optimized protocol, two series of new aryl-1,2,3-triazole-&beta carboline hybrids have been designed and synthesized, and the chemical structures were characterized by 1H NMR, 13C NMR, and high-resolution mass spectrometry (HRMS). All of the target compounds were evaluated in vitro for their antifungal activity against Rhizoctorzia solani, Fusarium oxysporum, Botrytis cinerea Pers., sunflower sclerotinia rot, and rape sclerotinia rot by mycelia growth inhibition assay at 50 &mu g/mL. The antifungal evaluation of the novel hybrids showed that, among the tested compounds, 5a, 5b, 5c, and 9b showed good antifungal activity against sunflower sclerotinia rot. Specifically, compound 9b also exhibited high broad-spectrum fungicidal against all the tested fungi with inhibition rates of 58.3%, 18.52%, 63.07%, 84.47%, and 81.23%. However, for F. oxysporum, all the target compounds showed no in vitro antifungal activities with an inhibition rate lower than 20%. These results provide an encouraging framework that could lead to the development of potent novel antifungal agents. |
| Databáze: | OpenAIRE |
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