苯并[c]菲啶和橙酮类化合物的设计、合成与生物活性研究
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摘要
基于从天然活性物质中开发的农药具有高效、抗性发展缓慢和环境相容好等优点,为了开发新的农药品种,本文以生物活性的苯并[c]菲啶型生物碱和橙酮两类天然产物为先导化合物,对其进行结构改造与修饰,共合成了116种不同结构类型的目标化合物,它们的结构均经~1H NMR和HRMS验证,其中的103个化合物还经~(13)C NMR验证,部分化合物还得到了IR光谱、2D NMR、X-ray单晶衍射的进一步确认。所合成的化合物具有较好的生物活性,结构与活性之间存在一定的构效关系,为今后的工作打下了一定的基础,具体内容如下:
第一部分以我国研制的植物源农药的活性成分血根碱——苯并[c]菲啶型生物碱为先导化合物研究开发新型的杀虫、杀菌剂及植物生长调节剂等,对苯并[c]菲啶骨架进行改造与修饰,主要考查了苯并[c]菲啶环上C(11)-C(12)键的变化、11-位取代基及6-位氨基上取代基的变化对生物活性的影响,共合成了57个目标化合物,发现部分化合物具有较好的杀菌和促进黄瓜子叶生根活性,在50μg·mL~(-1)的剂量下对花生褐斑的抑制率可以达到70.0%,在10μg·mL~(-1)的剂量下对黄瓜子叶生根的促进率可以达到88.6%;重要的是,该类化合物还具有强烈的抗癌活性,抑制人乳腺癌(MCF-7)和人肝细胞癌(HepG2)的IC_(50)分别为0.37和1.05μg·mL~(-1),具有进一步开发或作为先导化合物继续研究的价值。
而且,以叔丁醇钾(t-BuOK)做碱、1,3-二甲基-4H-2-嘧啶酮(DMPU)为溶剂,邻甲基苯腈可发生自缩合反应生成1-氨基-3-(2-甲基苯基)异喹啉,结构得到了X-ray单晶衍射的验证,提供了一条合成3-芳基异喹啉化合物的简便方法。
第二部分以化感抑草活性物质——橙酮为先导化合物,研究开发新型的除草剂,主要对橙酮的A环和B环进行结构改造与修饰,重点研究了B环(即Ar部分)的变化对除草活性的影响,优化了合成路线,合成了59个目标化合物,发现了更高除草活性的化合物,在10μg·mL~(-1)时对油菜根长的抑制率为81.3%;并发现该类化合物具有强烈抑制油菜种子萌发的作用;个别4,6-二乙氧基橙酮降低测试浓度除草活性反而升高,可能存在一种新的除草作用机制,有待于进一步的深入研究。
Owing to the advantages of natural active product as lead compounds,in this thesis,116 target compounds were designed and synthesized based on sanguinarine and arone.All compounds have been characterized by ~1H NMR and HRMS,and 103 of them have been identified by ~(13)C NMR,and some of them have been further confirmed by IR,2D NMR and X-ray single-crystal diffraction.Preliminary bioassay shows that all of them possess some extent biological activity,and there exist structure-activity relationships between them.
Firstly,57 benzo[c]phenanthridine compounds were designed and synthesized based on sanguinarine,a benzo[c]phenanthridine alkaloid,which is a new plant-derived pesticide,and the research was mainly focused on the midification of the bond of C(11)-C(12),11-substituent and 6-amino of the benzo[c]phenanthridine ring.Preliminary bioassay shows that some of them have high fungicidal activity and promoting cucumber cotyledon root-formation activity at extent experimental dosage. It is important that these benzo[c]phenanthridines have excellent antitumor activities, and can be further investigated as lead compounds.
Besides,a facile self-condensation of o-tolunitrile promoted by potassium tert-butanolate in DMPU to synthesize 3-arylisoquinoline derivative was found,and its structure was characterized by X-ray single-crystal diffraction.
Secondly,in order to find new herbicide,59 aurones were designed and synthesized based on arone,an allelocherniacal from dee(PI312777).The research was mainly focused on the midification of A and B rings of aurone and more attention was paid on B ring.The in vitro bioassay result demonstrats that some aurones have high herbicidal activity(81.3%),at the dosage of 10μg·mL~(-1).Moreover,some aurones can strongly inhibit seeds germination of Brassica napus.In addition,the herbicidal activity of 4,6-diethoxyaurones against Brassica napus appears abnormal, this may suggest a new mechanism.
第一部分以我国研制的植物源农药的活性成分血根碱——苯并[c]菲啶型生物碱为先导化合物研究开发新型的杀虫、杀菌剂及植物生长调节剂等,对苯并[c]菲啶骨架进行改造与修饰,主要考查了苯并[c]菲啶环上C(11)-C(12)键的变化、11-位取代基及6-位氨基上取代基的变化对生物活性的影响,共合成了57个目标化合物,发现部分化合物具有较好的杀菌和促进黄瓜子叶生根活性,在50μg·mL~(-1)的剂量下对花生褐斑的抑制率可以达到70.0%,在10μg·mL~(-1)的剂量下对黄瓜子叶生根的促进率可以达到88.6%;重要的是,该类化合物还具有强烈的抗癌活性,抑制人乳腺癌(MCF-7)和人肝细胞癌(HepG2)的IC_(50)分别为0.37和1.05μg·mL~(-1),具有进一步开发或作为先导化合物继续研究的价值。
而且,以叔丁醇钾(t-BuOK)做碱、1,3-二甲基-4H-2-嘧啶酮(DMPU)为溶剂,邻甲基苯腈可发生自缩合反应生成1-氨基-3-(2-甲基苯基)异喹啉,结构得到了X-ray单晶衍射的验证,提供了一条合成3-芳基异喹啉化合物的简便方法。
第二部分以化感抑草活性物质——橙酮为先导化合物,研究开发新型的除草剂,主要对橙酮的A环和B环进行结构改造与修饰,重点研究了B环(即Ar部分)的变化对除草活性的影响,优化了合成路线,合成了59个目标化合物,发现了更高除草活性的化合物,在10μg·mL~(-1)时对油菜根长的抑制率为81.3%;并发现该类化合物具有强烈抑制油菜种子萌发的作用;个别4,6-二乙氧基橙酮降低测试浓度除草活性反而升高,可能存在一种新的除草作用机制,有待于进一步的深入研究。
Owing to the advantages of natural active product as lead compounds,in this thesis,116 target compounds were designed and synthesized based on sanguinarine and arone.All compounds have been characterized by ~1H NMR and HRMS,and 103 of them have been identified by ~(13)C NMR,and some of them have been further confirmed by IR,2D NMR and X-ray single-crystal diffraction.Preliminary bioassay shows that all of them possess some extent biological activity,and there exist structure-activity relationships between them.
Firstly,57 benzo[c]phenanthridine compounds were designed and synthesized based on sanguinarine,a benzo[c]phenanthridine alkaloid,which is a new plant-derived pesticide,and the research was mainly focused on the midification of the bond of C(11)-C(12),11-substituent and 6-amino of the benzo[c]phenanthridine ring.Preliminary bioassay shows that some of them have high fungicidal activity and promoting cucumber cotyledon root-formation activity at extent experimental dosage. It is important that these benzo[c]phenanthridines have excellent antitumor activities, and can be further investigated as lead compounds.
Besides,a facile self-condensation of o-tolunitrile promoted by potassium tert-butanolate in DMPU to synthesize 3-arylisoquinoline derivative was found,and its structure was characterized by X-ray single-crystal diffraction.
Secondly,in order to find new herbicide,59 aurones were designed and synthesized based on arone,an allelocherniacal from dee(PI312777).The research was mainly focused on the midification of A and B rings of aurone and more attention was paid on B ring.The in vitro bioassay result demonstrats that some aurones have high herbicidal activity(81.3%),at the dosage of 10μg·mL~(-1).Moreover,some aurones can strongly inhibit seeds germination of Brassica napus.In addition,the herbicidal activity of 4,6-diethoxyaurones against Brassica napus appears abnormal, this may suggest a new mechanism.
引文
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