Study On The Synthesis And Bioactivity Of Coumarin Derivatives

Coumarins, also known as a large class of plant secondary metabolites, are present in remarkable amounts in plants, and their presence has also been found in animal and microorganisms sources. coumarins and their derivatives possess a wide range of biological activities. For instance, they have been claimed to be used as anti-bacteria, anti-HIV, anti-tumor, anti-inflammation, anti-coagulation and insecticidal activity and so on. Twenty seven of coumarin derivatives were prepared from hydroxycoumarin their bioactivities such as insecticidal activity, anti-tumor activity were also evaluated. The corresponding work was described as follows:1. the development on the synthesis and bioactivities of coumarin derivatives was reviewed.2. Twenty seven coumarin derivatives derivatives were synthesized by esterification and Williamson etherification successively from7-hydroxycoumarin and4-hydroxycoumarin. All compounds obtained were characterized by’HNMR and13CNMR, and the new compounds were also confirmed by HR MS spectra.3. The antifeedant activities, insecticidal activities of the synthesized compounds against Mythimna separata were examined by using the conventional no-choice leaf-disk method and the dipping experiment, respectively. Compared to tutin, most of the tested compounds showed better antifeedant and insecticidal activities. Compounds Ⅰ-2,Ⅰ-6,Ⅰ-8,Ⅰ-10, Ⅱ-4and Ⅱ-6demonstrated strong antifeeding rates, which were11.8-22.9%and49.0-68.8%higher than tutin at24h and48h. After24h, the LC50value of compounds Ⅰ-2, Ⅰ-6, Ⅱ-10and tutin were1.84mg/mL,1.43mg/mL,1.88mg/mL,6.65mg/mL, respectively4. SRB assay was used to screen synthetic coumarin derivatives in vitro activity against SK-N-SH cells. The results indicated that compounds Ⅰ-14、Ⅰ-15、Ⅱ-5and Ⅱ-12had greater inhibiting effect on SK-N-SH cell lines and all the LC50values of them were less than1OμM. Their bioactivities and structure-bioactivity relationship provide a reliable experimental and theoretical basis for further design and research of potent anticancer drugs.