Synthesis And Application Of New Thiochromones Photolabile Protecting Groups

Photolabile protecting groups(PPGs)are a class of compounds that contain chromophore groups.Compared with conventional protecting groups,the release of substrate(which are protected by PPGs)will proceeed smoothly without additive such as acid,alkali and so on.Under the irradiation of specific wavelength light,the substrate controlled to release with high spatial and temporal resolution.In this paper,employing thiophenol,P2O5 and phosphoric acid as the starting materials,four thiochromones photolabile protecting groups was synthesized by condensation reaction,halogenation reaction,Suzuki reaction,reduction reaction and oxidation reaction.Then,these photolabile protecting groups were applied in the protection and photodeprotection of carboxy compounds,phosphoric acid compounds and amino compounds.In order to expand the application of thiochromones photolabile protecting groups,three anthraquinone anticancer drugs were synthesized.And the protection of these drugs were successfully obtained with the PPGs.The photodeprotection reactions wre studied with the irradiatation wavelength in 365 nm.With the irradiatation of the light whose wavelength is 365 nm,the deprotection was completed in 14 min with the yeild of more than 99%.Meanwhile,the photodeprotection reaction was proceeded under mild condition without any other agents.The PPGs with this charateristic are potential to be applied in the biological system.We also tested the antitumor activity of anthraquinone anticancer drugs and its protected product in vitro.It was found that the toxicity reduced after the drugs were protected with the PPGs.