Benzo [c] Phenanthridine And Orange Ketones Design, Synthesis And Biological Activity

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 ¹³C 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.