内酯类天然产物及其类似物的合成与生物活性研究
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摘要
随着现代农业的发展,环保、绿色的农药越来越受到关注。传统农药具有毒性高、难以降解等缺点,而以天然产物为先导化合物开发得到的新型农药具有绿色、环境兼容性好等优点,因此此类新型农药品种的研发具有重要意义。
本文分为两部分：第一部分,探索了3-溴甲基-5-H-呋喃-2-酮在合成α-亚甲基-γ-丁内酯类化合物中的应用,并且之后将其应用于(+)-8-Epigrosheimin的全合成,；后以香豆素类天然产物为先导化合物,进行结构修饰,寻求开发新的绿色农药。所合成化合物结构都经过’HNMR、13C NMR、HRMS的表征。香豆素类化合物的初步生物活性测试显示,此类化合物有一定除草活性,具有作为先导化合物继续研究的价值,为今后此方向的工作打下了一定基础。具体内容如下：
第一部分,探索了3-澳甲基-5-H-呋喃-2-酮在金属锌与铟的参与下与醛耦合合成α-亚甲基-γ-丁内酯类化合物的反应。该反应显示了良好的化学选择性,并没有观察到其他副产物,得到共计17个化合物；同时,与锌相比,铟参与的Barbier反应具有更好的立体选择性,并且所用溶剂为水,反应更加绿色,具有很好的实际利用价值。该方法相比于其他合成α-亚甲基-γ-丁内酯结构的方法来说,操作简单,反应条件温和,产率较高,应用范围广,不存在反应条件苛刻以及产率低等缺点,在今后合成α-亚甲基-γ-丁内酯结构化合物时会发挥重要作用；之后将3-溴甲基-5-H-呋喃-2-酮应用于(+)-8-Epigrosheimin的全合成,合成以(L)-香芹酮和3-溴甲基-5-H-呋喃-2-酮为原料,通过Barbier反应、分子内ENE反应为关键步骤,总共11步合成了(+)-8-Epigrosheimin,总产率45%。该化合物的合成验证了3-溴甲基-5-H-呋喃-2-酮在合成α-亚甲基-γ-丁内酯结构时的高效性,内酯结构与亚甲基结构同时构建大大的提高了合成效率；并且之后构建碳环骨架时,由于五元内酯环的刚性最终立体选择性的得到了产物,证明先构筑内酯环、然后构筑七元碳环骨架的合成策略是有效地,而且五元内酯环两个手性碳原子的立体构型可以通过底物手性诱导的方法来控制,其他先合成七元环骨架、后合成内酯的策略则不能很好的控制五元内酯环手性,同时α-亚甲基的构建也要通过多步反应,效率较低。因此该策略也可为今后对该种类化合物的生物活性研究以及构效关系研究提供非常便捷的合成方法。
第二部分,以天然产物4-羟基香豆素为先导化合物,在3位引入苯甲酰基行进结构修饰,合成了与三酮化合物结构相似的3-苯甲酰基-4-羟基香豆素类化合物,共计48个化合物,随后测试了该类化合物对油菜和稗草的抑制活性。测试结果表明,所有此类化合物都对油菜具有一定活性,可是对于稗草则没有明显活性,说明此类化合物对双子叶植物有抑制作用,而对单子叶植物没有明显抑制作用。此类化合物虽然也具有三酮类化合物的结构,但是从除草结果来看,3-苯甲酰基-4-羟基香豆素类化合物可能具有与三酮类化合物不同的除草作用机制。针对其对油菜的活性,我们将继续研究具有较高活性的该类化合物,希望通过了解其除草作用机制来开发新型的除草剂。
Environment friendly and green pesticides are paid more attention with the development of modern agriculture. Traditional pesticides have played an important role in the past years, but as high toxical compounds that hard to be degraded, they have also produced environment and social problems. Meantime, lead compounds based on natural product can be developed to be green,degradable pesticides, which means the research of this field will be very important.
In this paper, the application of3-bromomethyl-5-H-furan-2-one in the synthesis of a-methylene-y-butyrolactone was explored as Zinc or Indium-mediated, and (+)-8-Epigrosheimin was total synthesized; then we made the structure modification of4-hydroxycoumarin to develop new green pesticide. There were65compounds synthesized and they were all characterized by1H NMR,13C NMR, HRMS. The preliminary bioassay of coumarin compounds shows that they proceed certain herbicidal bioactivity and can be researched as lead compounds, the work in the future can be continued. The work are as follows:
We investigated the reactions of3-bromomethyl-5-H-furan-2-one with aldehyde in the presence of metal Zinc and Indium, as that's an efficient route to synthesize a-methylene-y-butyrolactone which is a popular structure in many nature products. The chemoselectivity of reaction is quite well, no byproducts were observed and17compounds were synthesized. Meanwhile, compared to Zinc, the stereoselectivity of reaction that mediated by Indium was better; and water was used as solvent in the reaction, that's more environment-friendly. Compared to the other method for the synthesis of a-methylene-y-butyrolactone, our ideal is more effective because the reaction is easier to operate, the conditions are more mild, yields are higher. There is no doubt that this method will be more and more used in the synthesis of the compounds that obtain the structure of a-methylene-y-butyrolactone.
Then we synthesized (+)-8-Epigrosheimin from (JL)-Carvone and3-bromomethyl-5-H-furan-2-one after11steps, in which Barbier reaction and intramolecular ENE reaction were the key steps, and final yield reached45%. The synthesis proved that3-bromomethyl-5-H-furan-2-one is a useful compound for the synthesis of a-methylene-y-butyrolactone, formation of methylene and lactone improved the efficiency of synthesis remarkable. When we obtained the seven membered carbon ring, rigidity of lactone lead to enantioselective synthesis of final compound, which proved our strategy that formation of lactone was proceeded before carbon ring was right; during the reaction, two chiral centers in the lactone were precisely obtained because the chiral conduction from the starting compound. Compared to the methods that carbon ring was synthesized first and lactone was obtained later, our strategy got an advantage of chiral contral. The methods that have been reported to format a-methylene need certain steps and efficiency is poor, so our method provided a useful way for the synthesis of Epigrosheimin derivatives, which is good for the study of their bioactivitives and structure-activity relationship.
At last,3-benzoyl-4-hydroxycoumarin derivatives that have a similar structure with sulcotrione were synthesized from4-hydroxycoumarin which is a lead compound. Herbicidal activities were investigated. The results showed that all compounds were active selectively against brassic campestris, nearly no activities against Echinochloa crusgalli, which means these compounds got the inhibition against dicotyledon but monocotyledon. Obviously, it goes the different way in the field of herbicidal activities, compared the commercial herbicide such as sulcotrione or mesotrione. It is quite necessary for us the find the3-benzoyl-4-hydroxycoumarin derivatives that obtain better Herbicidal activities against brassic campestris, after this we will investigate how these compounds work, so as to explode a new herbicide.
本文分为两部分：第一部分,探索了3-溴甲基-5-H-呋喃-2-酮在合成α-亚甲基-γ-丁内酯类化合物中的应用,并且之后将其应用于(+)-8-Epigrosheimin的全合成,；后以香豆素类天然产物为先导化合物,进行结构修饰,寻求开发新的绿色农药。所合成化合物结构都经过’HNMR、13C NMR、HRMS的表征。香豆素类化合物的初步生物活性测试显示,此类化合物有一定除草活性,具有作为先导化合物继续研究的价值,为今后此方向的工作打下了一定基础。具体内容如下：
第一部分,探索了3-澳甲基-5-H-呋喃-2-酮在金属锌与铟的参与下与醛耦合合成α-亚甲基-γ-丁内酯类化合物的反应。该反应显示了良好的化学选择性,并没有观察到其他副产物,得到共计17个化合物；同时,与锌相比,铟参与的Barbier反应具有更好的立体选择性,并且所用溶剂为水,反应更加绿色,具有很好的实际利用价值。该方法相比于其他合成α-亚甲基-γ-丁内酯结构的方法来说,操作简单,反应条件温和,产率较高,应用范围广,不存在反应条件苛刻以及产率低等缺点,在今后合成α-亚甲基-γ-丁内酯结构化合物时会发挥重要作用；之后将3-溴甲基-5-H-呋喃-2-酮应用于(+)-8-Epigrosheimin的全合成,合成以(L)-香芹酮和3-溴甲基-5-H-呋喃-2-酮为原料,通过Barbier反应、分子内ENE反应为关键步骤,总共11步合成了(+)-8-Epigrosheimin,总产率45%。该化合物的合成验证了3-溴甲基-5-H-呋喃-2-酮在合成α-亚甲基-γ-丁内酯结构时的高效性,内酯结构与亚甲基结构同时构建大大的提高了合成效率；并且之后构建碳环骨架时,由于五元内酯环的刚性最终立体选择性的得到了产物,证明先构筑内酯环、然后构筑七元碳环骨架的合成策略是有效地,而且五元内酯环两个手性碳原子的立体构型可以通过底物手性诱导的方法来控制,其他先合成七元环骨架、后合成内酯的策略则不能很好的控制五元内酯环手性,同时α-亚甲基的构建也要通过多步反应,效率较低。因此该策略也可为今后对该种类化合物的生物活性研究以及构效关系研究提供非常便捷的合成方法。
第二部分,以天然产物4-羟基香豆素为先导化合物,在3位引入苯甲酰基行进结构修饰,合成了与三酮化合物结构相似的3-苯甲酰基-4-羟基香豆素类化合物,共计48个化合物,随后测试了该类化合物对油菜和稗草的抑制活性。测试结果表明,所有此类化合物都对油菜具有一定活性,可是对于稗草则没有明显活性,说明此类化合物对双子叶植物有抑制作用,而对单子叶植物没有明显抑制作用。此类化合物虽然也具有三酮类化合物的结构,但是从除草结果来看,3-苯甲酰基-4-羟基香豆素类化合物可能具有与三酮类化合物不同的除草作用机制。针对其对油菜的活性,我们将继续研究具有较高活性的该类化合物,希望通过了解其除草作用机制来开发新型的除草剂。
Environment friendly and green pesticides are paid more attention with the development of modern agriculture. Traditional pesticides have played an important role in the past years, but as high toxical compounds that hard to be degraded, they have also produced environment and social problems. Meantime, lead compounds based on natural product can be developed to be green,degradable pesticides, which means the research of this field will be very important.
In this paper, the application of3-bromomethyl-5-H-furan-2-one in the synthesis of a-methylene-y-butyrolactone was explored as Zinc or Indium-mediated, and (+)-8-Epigrosheimin was total synthesized; then we made the structure modification of4-hydroxycoumarin to develop new green pesticide. There were65compounds synthesized and they were all characterized by1H NMR,13C NMR, HRMS. The preliminary bioassay of coumarin compounds shows that they proceed certain herbicidal bioactivity and can be researched as lead compounds, the work in the future can be continued. The work are as follows:
We investigated the reactions of3-bromomethyl-5-H-furan-2-one with aldehyde in the presence of metal Zinc and Indium, as that's an efficient route to synthesize a-methylene-y-butyrolactone which is a popular structure in many nature products. The chemoselectivity of reaction is quite well, no byproducts were observed and17compounds were synthesized. Meanwhile, compared to Zinc, the stereoselectivity of reaction that mediated by Indium was better; and water was used as solvent in the reaction, that's more environment-friendly. Compared to the other method for the synthesis of a-methylene-y-butyrolactone, our ideal is more effective because the reaction is easier to operate, the conditions are more mild, yields are higher. There is no doubt that this method will be more and more used in the synthesis of the compounds that obtain the structure of a-methylene-y-butyrolactone.
Then we synthesized (+)-8-Epigrosheimin from (JL)-Carvone and3-bromomethyl-5-H-furan-2-one after11steps, in which Barbier reaction and intramolecular ENE reaction were the key steps, and final yield reached45%. The synthesis proved that3-bromomethyl-5-H-furan-2-one is a useful compound for the synthesis of a-methylene-y-butyrolactone, formation of methylene and lactone improved the efficiency of synthesis remarkable. When we obtained the seven membered carbon ring, rigidity of lactone lead to enantioselective synthesis of final compound, which proved our strategy that formation of lactone was proceeded before carbon ring was right; during the reaction, two chiral centers in the lactone were precisely obtained because the chiral conduction from the starting compound. Compared to the methods that carbon ring was synthesized first and lactone was obtained later, our strategy got an advantage of chiral contral. The methods that have been reported to format a-methylene need certain steps and efficiency is poor, so our method provided a useful way for the synthesis of Epigrosheimin derivatives, which is good for the study of their bioactivitives and structure-activity relationship.
At last,3-benzoyl-4-hydroxycoumarin derivatives that have a similar structure with sulcotrione were synthesized from4-hydroxycoumarin which is a lead compound. Herbicidal activities were investigated. The results showed that all compounds were active selectively against brassic campestris, nearly no activities against Echinochloa crusgalli, which means these compounds got the inhibition against dicotyledon but monocotyledon. Obviously, it goes the different way in the field of herbicidal activities, compared the commercial herbicide such as sulcotrione or mesotrione. It is quite necessary for us the find the3-benzoyl-4-hydroxycoumarin derivatives that obtain better Herbicidal activities against brassic campestris, after this we will investigate how these compounds work, so as to explode a new herbicide.
引文
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