The Synthesis Of New Coumarin Derivatives And The Research Of Their Properties

Coumarin is a kind of organic heterocyclic compound containing benzopyrone structure.Its molecular structure is unique with good thermodynamics and photochemical stability.Due to the large conjugation system and strong electron transfer ability in the molecule,it is easy to carry out structural modification and introduce a variety of functional groups,so that coumarin derivatives have a wide range of applications in the biomedical,functional materials,food and other fields.In this paper,15 novel coumarin derivatives which were divided into three series were synthesized.We studied their ultraviolet spectrum properties,electrochemical properties and antibacterial,antitumor activities.1.We were based on coumarin,7-hydroxy coumarin and 4-methyl umbelliferone as raw materials through nitration,reduction reaction and condensation.By DCC/DMAP dehydration system,We combined ferrocenyl butyric acid,ferrocenoylpropionic acid,phenylbutyric acid with the modified coumarin intermediates respectively,finally synthesized 3 series,a total of 15 new coumarin compounds Fc L1~Fc L5,Fc L6~Fc L10 and Ph L11~Ph L15.The structures of compounds were characterized by IR,1H NMR,13 C NMR and elemental analysis.The crystal structures of three target compounds Fc L3?Fc L6 and Ph L13 was determined by X-Ray diffraction analysis.2.We studied electrochemical properties of containing ferrocenyl coumarin compounds by Cyclic Voltammetry and Normal Pulse Voltammetry.The results showed the redox reaction on the surface of electrode were reversible with single electron and controlled by diffusion.3.In the first,15 target compounds were screened by disc diffusion method.The results showed the compounds were not effective against Gram negative bacteria,only had positive effect on Gram positive bacteria,and then Gram positive bacteriaStaphylococcus aureus were evaluated in detail by broth microdilution method.The results showed that the MIC value of nitro-containing compounds was significantly smaller than that of other compounds,indicating that the introduction of nitro group greatly enhanced the antibacterial activities.4.The antitumor activities of all newly synthetic coumarin derivatives on six kinds of cancer cells were evaluated by CCK-8 assay.The results showed Fc L1~Fc L5 and Ph L11~Ph L15 exhibited similar antitumor activities and selectivities against BIU-87,SGC-7901 and MCF-7 cells.In addition,the structure-activity relationship studies showed that the introduction of methyl and amide groups can improve the antitumor activities of the compounds.