长叶烯衍生二苯醚羧酸类化合物的合成、抗真菌活性、3D-QSAR 和水滑石载药研究。
Synthesis, Antifungal Activity, 3D-QSAR and Controlled Release on Hydrotalcite Study of Longifolene-Derived Diphenyl Ether Carboxylic Acid Compounds.
机构信息
School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China.
Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products, Guangxi Minzu University, Nanning 530006, China.
出版信息
Molecules. 2023 Feb 16;28(4):1911. doi: 10.3390/molecules28041911.
Twenty-two novel longifolene-derived diphenyl ether-carboxylic acid compounds were synthesized from renewable biomass resources longifolene, and their structures were confirmed by FT-IR, H NMR, C NMR, and HRMS. The preliminary evaluation of in vitro antifungal activity displayed that compound presented inhibition rates of 85.9%, 82.7%, 82.7%, and 81.4% against , and , respectively, and compound possessed inhibition rates of 80.7%, 80.4%, and 80.3% against , , , respectively, exhibiting excellent and broad-spectrum antifungal activities. Besides, compounds and showed significant antifungal activities with inhibition rates of 81.2% and 80.7% against , respectively. Meanwhile, a reasonable and effective 3D-QSAR mode ( = 0.996, = 0.572) has been established by the CoMFA method. Furthermore, the drug-loading complexes were prepared and characterized. Their pH-responsive controlled-release behavior was investigated as well. As a result, complex exhibited excellent controlled-releasing performance in the water/ethanol (10:1, v:v) and under a pH of 5.7.
从可再生生物质资源长叶烯出发，合成了 22 种新型长叶烯衍生的二苯醚羧酸化合物，并通过傅里叶变换红外光谱（FT-IR）、氢核磁共振谱（H NMR）、碳核磁共振谱（C NMR）和高分辨质谱（HRMS）确证了其结构。初步的体外抗真菌活性评价结果表明，化合物 对 、 、 和 表现出 85.9%、82.7%、82.7%和 81.4%的抑制率，化合物 对 、 、 和 表现出 80.7%、80.4%和 80.3%的抑制率，表现出优异而广谱的抗真菌活性。此外，化合物 和 对 表现出显著的抗真菌活性，抑制率分别为 81.2%和 80.7%。同时，采用 CoMFA 方法建立了合理有效的 3D-QSAR 模型（ = 0.996， = 0.572）。此外，还制备并表征了载药配合物 ，并研究了其在不同 pH 值下的响应性控释行为。结果表明，配合物 在水/乙醇（10:1，v:v）和 pH 值为 5.7 的条件下表现出优异的控释性能。
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