基于丁香酚的异唑啉类化合物的设计合成及抑菌活性

Design, synthesis and fungicidal activity of novel isoxazolines from eugenol

为了探索新型异齅唑啉类化合物作为杀菌剂候选化合物开发的潜力,本研究以廉价易得的芳香醛类化合物为原料制备了32个氯代肟类化合物,通过其与天然产物丁香酚的1,3-偶极环加成反应和后期官能团化反应,制备了35个异齅唑啉类化合物（D1~D32,E1~E3）,其中34个为新化合物。所有化合物的结构均经过液相色谱-电喷雾质谱（LC-ESI-MS）、核磁共振氢谱（^1HNMR）及元素分析确认。初步抑菌活性测试结果表明：多数目标化合物对油菜菌核病菌、水稻纹枯病菌、番茄早疫病菌和辣椒疫霉病菌具有较好的抑菌活性,其中化合物D26对油菜菌核病菌的活性最高,有效抑制中浓度（EC50）为14.3 mg/L,具有进一步研究的价值。

In order to discover new fungicidal lead compounds, 35 isoxazolines have been synthesised（D1-D32, E1-E3）, among which 34 isoxazolines are novel compounds. In this synthesis, 32 chlorinated oximes were first synthesized from commercially available and inexpensive aromatic aldehydes. The following 1, 3-dipolar cycloaddition with the natural product eugenol and late-stage functionalization furnished the target compounds.The synthesized compounds were characterized by LC-ESI-MS, ~1HNMR and elemental analyses. Preliminary bioactivity tests showed that the synthesized isoxazolines demonstrated good activity against Sclerotinia sclerotiorum, Rhizoctonia solani, Alternaria solani and Phytophthora capsici. Compound D26 has the best inhitory effect against S. sclerotiorum with the EC_50 value of 14.3 mg/L, which can be used as a novel lead compound for the discovery of new antifungal leads.