The Molecular Recognition Behavior Of ?-Cyclodextrins And Its Derivatives With Drugs And Their Catalytic Study On Green Organic Chemistry

Cyclodextrin(CD) is one of the most important macromoleculars, because of its special structure of lipophilic central cavity, which has been widely used in pharmaceutic preparation? catalysis of organic chemistry and artificial enzyme models. In recent years, using as catalyst of cyclodextrin has become the hot research issue. In order to further explore the catalytic property of cyclodextrin and its derivatives, we designed and synthesized a new cyclodextrin derivative which can efficiently catalyze Suzuki-Miyaura cross-coupling reaction and the reduction of nitroarenes in water under mild conditions. In addition, we also have synthesiezed several oxazolidine-cyclodextrin derivatives and these series compounds can catalyse the aldo reaction. However, the value of ee was two little. Moreover, we prepared the inclusion complex of Podophyllotoxin (PPT) with ?-CD and the inclusion complex was carefully charactered. The research mainly divided into three aspects:1. In this study, a new kind of water-soluble, macromolecular palladium complex catalyst DACH-Pd-?-CD for Suzuki-Miyaura coupling reaction had been successfully prepared and characterized by NMR, XRD, TEM, HR-TEM and EDS. The catalyst showed excellent activity to Suzuki-Miyaura cross-coupling reaction and the yields of most desired products are from 88% to 99%. The catalytic performance is still wonderful and without catalyst loss after ten cycles. In addition, it also showed high catalytic performance in the reduction of different nitroarenes to the corresponding anilines with the presence of sodium borohydride in water at room temperature. The yields of the desired products are up to 99%. Furthermore, the catalyst can be easily separated and still could maintain high catalytic activity after five cycles and no leaching of Pd into solution occurred.2. In addition, we also have synthesiezed several oxazolidine-cyclodextrin derivatives and these series compounds can catalyse the aldo reaction. However, the value of ee was two little.3. In this study, the inclusion complex of PPT with ?-CD was successfully prepared. The formation of the PPT/y-CD inclusion complex was carefully characterized using 1H NMR. 2D NMR. XRD analysis, and DSC. The NMR spectrum indicated that PPT molecules were mostly inserted into the wide side of the cavity with A. B. C. and D rings in the interior of ?-CD. The fluorescence spectra and Job plot successfully demonstrated that the inclusion complex was significantly stable with stability constant K, (4245.5 L·mol-1) and a stoichiometry of 1:1. Moreover, the water solubility of PPT significantly improved with the formation of the inclusion complex. Most importantly, the toxity of PPT reduced to an appropriate degree to be a kind of antitumor drug comparing with cis-platinum, which probably provided a chance to expand its clinical applications. The inclusion complex was also confirmed to be safe through the experiment on mice.