Synthesis Of Two Kinds Of 28-O-substituent Betulone Thiosemicarbazone And Their Metal Complexes

Betulin, a pentacyclic triterpenoids, has been demonstrated with many biological activities such as anti-inflammatory, anti-inflammatory, anti-viral and anti-tumor effects and other effects.Thiosemicarbazone group is a unique Schiff base. Its complexes with transition metals of a variety of biological activities, such as anti-tumor, anti-bacterial, anti-inflammatory and so on. And thiosemicarbazone metal complex due to having good stability, low toxicity, good biocompatibility and many other advantages concern. Thus, this thesis introduction of thiosemicarbazone betulin backbone and coordinate with the transition metals, in order to obtain physiological activity better and more efficient compound.This thesis, the raw material for the betulin (extraction from birch bark), First we use the Ph33CCl to protect the hydroxyl of betulin C-28 and C-3 hydroxyl group is oxidized, then deprotection of betulin C-28, esterification, introducing thiosemicarbazone, and finally coordinate with transition metal ions to give the metal complexs (28-O-p-toluene sulfonyl betulone thiosemicarbazone metal complexes and 28-O-diethyl phosphoryl betulone thiosemicarbazone metal complexes). Synthesized two ligands and their copper (â…¡), silver (â… ), cadmium (â…¡), palladium (â…¡) metal complexes and characterization by the 1H-NMR, IR, MALDI-TOF-MS, Elemental analysis, TGA and other testing, and ultimately prove its metal complexes for two ligands with metal ions form bidentate mode. And synthesis of two ligands and their metal complexes were conducted in vitro experiments with cancer cell proliferation assay.The results show that the copper (â…¡), silver (â… ), cadmium (â…¡) metal complexs have good anti-proliferative effect in cell proliferation assay, and silver (â… ) metal complexs of ligands 2 of gram-positive bacteria and gram-negative bacteria have inhibited.