Sclerotiorin衍生物的合成及杀菌活性研究
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摘要
化学农药对解决世界粮食问题做出了非常突出的贡献,在未来相当长的一段时间里,仍将是农药的主体。然而,同一种农药或是相同作用机制农药的长期及大量施用,使得各种商品化农药的药效有着不同程度的下降、甚至失活,对农业、农民造成了巨大的损失。这就要求我们去开发具有新型结构骨架、新型作用靶标的农药来满足现代农业生产的需要。
以天然产物为先导化合物而进行的农药分子设计,是近年来农药开发的一个重要组成部分。如吡咯类和甲氧基丙烯酸酯类杀菌剂,其具有独特作用机理,不仅活性高,且与已知杀菌剂无交互抗性。而天然产物sclerotiorin及其类似物表现出了非常广泛的生物活性,在农用杀菌方面具有很好的潜力。所以,本文以sclerotiorin为先导化合物,进行结构改造,以期合成一系列高杀菌活性的衍生物。
1、本文系统总结了天然产物azaphilone、sclerotiorin及其类似物的结构、合成及生物活性等方面的研究进展。
2、设计合成了6种结构类型共129个新型的sclerotiorin衍生物,所有合成的化合物均采用1H NMR和HRMS等手段进行了结构表征,并且获得了部分代表性化合物的晶体结构,对该类化合物的结构作了进一步的确定。
3、本文以sclerotiorin为先导化合物,首先对C-3位进行了结构改造,采用培养基法在20 ppm浓度下对腐霉菌(Pythium dissimile)、番茄早疫病菌(Alternaria solani)、葡萄灰霉菌(Botryotinia fuckeliana)和小麦赤霉病菌(Gibberella zeae)进行了活性筛选。活性测试表明,化合物Ⅱ-10对腐霉菌(Pythium dissimile)具有比较优异的杀菌活性。然后再以Ⅱ-10作为先导,对C-5位进行了结构改造,发现了化合物Ⅲ-1具有高效、广谱的杀菌活性；当测试浓度低至2 ppm时,部分化合物对腐霉菌仍表现出了超过80%的抑制活性。再以化合物Ⅲ-1作为二次先导,对C-7位的羟基进行乙酰化合成化合物Ⅲ-2,发现杀菌活性有所丧失,说明羟基的存在对活性有利；对C-2位的氧用氮来取代合成化合物Ⅲ-3,杀菌活性略有所下降,说明在C-2位引入氮原子对活性也是不利的；所以我们在保留C-7位羟基不变的前提下,对C-1位和C-5位作了进一步的结构改造,发现化合物Ⅳ-2中C-1位甲基的引入导致杀菌活性基本丧失；化合物Ⅳ-1中C-5位引入甲基使得杀菌活性有了进一步的提高,值得一提的是,该化合物对蚕豆单胞锈菌病菌(Uromyces viciae-fabae)、腐霉菌(Pythium dissimile)-.番茄早疫病菌(Alternaria solani)和小麦赤霉病菌(Gibberella zeae)都超过80%的抑制,体现了进一步研究的价值。
4、以上所有化合物通过进一步的杀菌活性筛选,发现合成的sclerotiorin衍生物在弱碱性环境下杀菌活性丧失,在阳光下化合物的半衰期很短(t1/2<2 h),增加化合物的稳定性是后续工作的重点。同时,我们发现天然产物karrikinolide具有和sclerotiorin类似的双环结构,但具有更好的稳定性。因此,希望引入呋喃并吡喃的结构,在提高稳定性的同时获得良好的杀菌活性。
5、本文初步总结sclerotiorin衍生物的结构和杀菌活性关系,为后续设计、合成更高生物活性衍生物提供理论指导。
Chemical pesticides have contributed a lot to solve the food problem in the world, which would also dominate the market of pesticides in the foreseeable future. However, the efficiency of many commercial pesticides has variably decreased due to the long and broad use of a single pesticide or several pesticides with the same modes of action, which has brought a great loss for agriculture. To satisfy the increasing agricultural production needs, it's highly desirable to develop new pesticides with novel skeletons or new target sites.
Recently, it's an important trend for the development of new pesticides with natural products as lead compounds. For example, fungicides with pyrrole or acrylic ester skeletons have unique modes of action, high bioactivity and no cross resistance with currently used fungicides. Considering the broad bioactivity of Sclerotiorin derivatives and their potential as fungicides, herein, we would like to synthesize a series of Sclerotiorin derivatives with highly fungicidal activity through structure modification.
1. This thesis has systematically summarized the structures, synthesis and bioactivities of azaphilone and Sclerotiorin derivatives.
2. We have designed and synthesized 6 different types and 129 new Sclerotiorin derivatives. All of them have been characterized by 1H NMR and HRMS, and some of them were confirmed by x-ray crystal structures.
3. In this thesis, we began with the structural modification for C-3 site with Sclerotiorin as lead compound and bioactivity screening under the concentration of 20ppm for various bacteria, such as Pythium dissimile, Alternaria solani, Botryotinia fuckeliana and Gibberella zeae. The results showed that compound 11-10 had better fungicidal acitivity for Phytophthora infestans and Pythium dissimile. WithⅡ-10 as lead compound, we further modified C-5 site, and compound III-1 was found to have excellent and broad fungicidal activity. With compound III-1 as second lead compound, further acylation of the hydroxyl group for C-7 site has shown no activity at all, which showed that hydroxyl group at C-7 site is benefical for its bioactivity. The substitution of oxygent at C-2 site with nitrogen for compound III-3 has shown little bioactivity drop and the nitrogen atom at C-2 site is unbenefical for its activity. Keeping hydroxyl group at C-7 site, we further modified the C-l and C-5 sites, and compoundsⅣ-1 andⅣ-2 were obtained. However, the introduction of methyl group at C1 site has significantly decreased the bioactivity. The introduction of methyl group at C-5 site in compound IV-1 has further improved its fungicidal acitivity. It was noted that, compoundⅣ-1 could realized 99% suppressing for Uromyces viciae-fabae, Pythium dissimile, Alternaria solani and Gibberella zeae, which showed the value for further studies.
4. All these compounds were screened with fungicial activity, and these compounds would lose their fungicidal activity under basic conditions, and have short half-life period under sunshine. The subsequent emphasis would focus on the increasing of their stabilities. Meanwhile, we found the natural product karrikinolide has similar bicyclic skeleton with sclerotiorin, which also has very good stability and bioactivity. Thus, we hope to obtain their derivatives with good fungicidal activity and high stability by introducing the furo[2,3-c]pyran skeleton.
5. This thesis firstly summarized the structure and fugicidal acitivty of sclerotiorin derivatives, which offered theorical guide for further design and synthesis of sclerotiorin derivatives with higher bioactivity.
以天然产物为先导化合物而进行的农药分子设计,是近年来农药开发的一个重要组成部分。如吡咯类和甲氧基丙烯酸酯类杀菌剂,其具有独特作用机理,不仅活性高,且与已知杀菌剂无交互抗性。而天然产物sclerotiorin及其类似物表现出了非常广泛的生物活性,在农用杀菌方面具有很好的潜力。所以,本文以sclerotiorin为先导化合物,进行结构改造,以期合成一系列高杀菌活性的衍生物。
1、本文系统总结了天然产物azaphilone、sclerotiorin及其类似物的结构、合成及生物活性等方面的研究进展。
2、设计合成了6种结构类型共129个新型的sclerotiorin衍生物,所有合成的化合物均采用1H NMR和HRMS等手段进行了结构表征,并且获得了部分代表性化合物的晶体结构,对该类化合物的结构作了进一步的确定。
3、本文以sclerotiorin为先导化合物,首先对C-3位进行了结构改造,采用培养基法在20 ppm浓度下对腐霉菌(Pythium dissimile)、番茄早疫病菌(Alternaria solani)、葡萄灰霉菌(Botryotinia fuckeliana)和小麦赤霉病菌(Gibberella zeae)进行了活性筛选。活性测试表明,化合物Ⅱ-10对腐霉菌(Pythium dissimile)具有比较优异的杀菌活性。然后再以Ⅱ-10作为先导,对C-5位进行了结构改造,发现了化合物Ⅲ-1具有高效、广谱的杀菌活性；当测试浓度低至2 ppm时,部分化合物对腐霉菌仍表现出了超过80%的抑制活性。再以化合物Ⅲ-1作为二次先导,对C-7位的羟基进行乙酰化合成化合物Ⅲ-2,发现杀菌活性有所丧失,说明羟基的存在对活性有利；对C-2位的氧用氮来取代合成化合物Ⅲ-3,杀菌活性略有所下降,说明在C-2位引入氮原子对活性也是不利的；所以我们在保留C-7位羟基不变的前提下,对C-1位和C-5位作了进一步的结构改造,发现化合物Ⅳ-2中C-1位甲基的引入导致杀菌活性基本丧失；化合物Ⅳ-1中C-5位引入甲基使得杀菌活性有了进一步的提高,值得一提的是,该化合物对蚕豆单胞锈菌病菌(Uromyces viciae-fabae)、腐霉菌(Pythium dissimile)-.番茄早疫病菌(Alternaria solani)和小麦赤霉病菌(Gibberella zeae)都超过80%的抑制,体现了进一步研究的价值。
4、以上所有化合物通过进一步的杀菌活性筛选,发现合成的sclerotiorin衍生物在弱碱性环境下杀菌活性丧失,在阳光下化合物的半衰期很短(t1/2<2 h),增加化合物的稳定性是后续工作的重点。同时,我们发现天然产物karrikinolide具有和sclerotiorin类似的双环结构,但具有更好的稳定性。因此,希望引入呋喃并吡喃的结构,在提高稳定性的同时获得良好的杀菌活性。
5、本文初步总结sclerotiorin衍生物的结构和杀菌活性关系,为后续设计、合成更高生物活性衍生物提供理论指导。
Chemical pesticides have contributed a lot to solve the food problem in the world, which would also dominate the market of pesticides in the foreseeable future. However, the efficiency of many commercial pesticides has variably decreased due to the long and broad use of a single pesticide or several pesticides with the same modes of action, which has brought a great loss for agriculture. To satisfy the increasing agricultural production needs, it's highly desirable to develop new pesticides with novel skeletons or new target sites.
Recently, it's an important trend for the development of new pesticides with natural products as lead compounds. For example, fungicides with pyrrole or acrylic ester skeletons have unique modes of action, high bioactivity and no cross resistance with currently used fungicides. Considering the broad bioactivity of Sclerotiorin derivatives and their potential as fungicides, herein, we would like to synthesize a series of Sclerotiorin derivatives with highly fungicidal activity through structure modification.
1. This thesis has systematically summarized the structures, synthesis and bioactivities of azaphilone and Sclerotiorin derivatives.
2. We have designed and synthesized 6 different types and 129 new Sclerotiorin derivatives. All of them have been characterized by 1H NMR and HRMS, and some of them were confirmed by x-ray crystal structures.
3. In this thesis, we began with the structural modification for C-3 site with Sclerotiorin as lead compound and bioactivity screening under the concentration of 20ppm for various bacteria, such as Pythium dissimile, Alternaria solani, Botryotinia fuckeliana and Gibberella zeae. The results showed that compound 11-10 had better fungicidal acitivity for Phytophthora infestans and Pythium dissimile. WithⅡ-10 as lead compound, we further modified C-5 site, and compound III-1 was found to have excellent and broad fungicidal activity. With compound III-1 as second lead compound, further acylation of the hydroxyl group for C-7 site has shown no activity at all, which showed that hydroxyl group at C-7 site is benefical for its bioactivity. The substitution of oxygent at C-2 site with nitrogen for compound III-3 has shown little bioactivity drop and the nitrogen atom at C-2 site is unbenefical for its activity. Keeping hydroxyl group at C-7 site, we further modified the C-l and C-5 sites, and compoundsⅣ-1 andⅣ-2 were obtained. However, the introduction of methyl group at C1 site has significantly decreased the bioactivity. The introduction of methyl group at C-5 site in compound IV-1 has further improved its fungicidal acitivity. It was noted that, compoundⅣ-1 could realized 99% suppressing for Uromyces viciae-fabae, Pythium dissimile, Alternaria solani and Gibberella zeae, which showed the value for further studies.
4. All these compounds were screened with fungicial activity, and these compounds would lose their fungicidal activity under basic conditions, and have short half-life period under sunshine. The subsequent emphasis would focus on the increasing of their stabilities. Meanwhile, we found the natural product karrikinolide has similar bicyclic skeleton with sclerotiorin, which also has very good stability and bioactivity. Thus, we hope to obtain their derivatives with good fungicidal activity and high stability by introducing the furo[2,3-c]pyran skeleton.
5. This thesis firstly summarized the structure and fugicidal acitivty of sclerotiorin derivatives, which offered theorical guide for further design and synthesis of sclerotiorin derivatives with higher bioactivity.
引文
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