从 3-蒈烯（II）合成生物活性化合物：（）-和（）-3-蒈烯-5-酮肟磺酸酯的合成、抗真菌活性和 3D-QSAR 研究。
Synthesis of Bioactive Compounds from 3-Carene (II): Synthesis, Antifungal Activity and 3D-QSAR Study of ()- and ()-3-Caren-5-One Oxime Sulfonates.
机构信息
School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, Guangxi, China.
Guangxi Academy of Forestry, Nanning 530002, Guangxi, China.
出版信息
Molecules. 2019 Jan 29;24(3):477. doi: 10.3390/molecules24030477.
A series of novel ()- and ()-3-caren-5-one oxime sulfonates were designed and synthesized in search of potent antifungal agents. The structures of the intermediates and target compounds were confirmed by UV-Vis, FTIR, NMR, and ESI-MS. The in vitro antifungal activity of the target compounds was preliminarily evaluated against , , , , and at 50 µg/mL. The bioassay results indicated that the target compounds exhibited the best antifungal activity against , in which compounds , , , , , , , , and had excellent inhibition rates of 100%, 100%, 100%, 92.9%, 92.9%, 92.9%, 92.9%, 85.7%, and 85.7%, respectively, showing much better antifungal activity than that of the commercial fungicide chlorothanil. Both the compounds and displayed outstanding antifungal activity of 100% against , and the former also displayed outstanding antifungal activity of 100% against . In order to design more effective antifungal compounds against , the analysis of three-dimensional quantitative structure-activity relationship (3D-QSAR) was carried out using the CoMFA method, and a reasonable and effective 3D-QSAR model (r² = 0.990, q² = 0.569) has been established.
我们设计并合成了一系列新型（±）-α-芳基-3-取代-5-氧代环己烷甲腈肟磺酸酯，以期获得高效的抗真菌药物。通过 UV-Vis、FTIR、NMR 和 ESI-MS 对中间体和目标化合物的结构进行了确认。初步评价了目标化合物对 、 、 、 、 和 的体外抗真菌活性，浓度为 50 µg/mL。生物测定结果表明，目标化合物对 表现出最佳的抗真菌活性，其中化合物 、 、 、 、 、 、 、 和 对 的抑制率均达到 100%，显示出比商品化杀菌剂氯噻啉更好的抗真菌活性。化合物 和 对 的抑制率均达到 100%，前者对 的抑制率也达到 100%。为了设计出更有效的抗真菌化合物来防治 ，我们采用 CoMFA 方法进行了三维定量构效关系（3D-QSAR）分析，并建立了一个合理有效的 3D-QSAR 模型（r² = 0.990，q² = 0.569）。
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