Design, Synthsis Of Salidroside And Rosavidine's Analogs

Fatigue and radiation became the most draconic problems with the living rhythm speeding up and pervasion of modern informational devices increasingly. Various kinds of actinogen existing in our living environment may probably cause the damage of organism, even induce carcinomatous change;Furthermore, the fatigue induced by living of fast rhythm and hyperbaric work could aggravate the extent of organism damage because of radiation. Therefore, the study of antifatigue and antiradiation drug appeared especially important.The study of antifatigue and antiradiation drug play a more important role in military medicine. In 21st century, electromagnetic radiation as a novel execute mode directly acting in human body induced the damage of central nervous system. At the same time, the more execute task, insufficient sleep, and fatigue caused by peospective war influenced legionary battle capability gravely. Consequently, the study of bifunctional drug possessing the ability of antifatigue and antiradiation simultaneously had enormously potentiality.Existing fgn and dom radioprotectant had categories mainly as sulfhydryl compound,Thioctic acids compound,Cytokine compound,Polysaccharide, cytokine, polysaccharide, and compound recipe,etc..The study of natural plant ingredient became hot spot owing to the side effect of front drugs. Main antifatigue applied domestic now are traditional Chinese drug, as Gold Theragran, ginseng, and acanthopanax, etc.. Comparatively speaking, Gold Theragran had smaller side effect while more notable pharmacodynamic action.Modern study of pharmacology revealed that Rhodiola possessed functions of anti-hypoxia, anti-fatigue, anti-radiation, antioxidation, anti-aging, and antitumor,etc.. The notable pharmacological action possessed undetachable relations with the containing chemical composition. Major active constitutent in rhodiola are salidroside,Ptyrosol,and Rosavin,etc..Salidroside belonged to glycoside compound. Glycosides,as well called glycoconjugate was formed by the dehydrolysis of saccharide or saccharide derivate and aglycone. Glycoside can be divided to oxo-glycoside,fluorouracil desoxyriboside,thioglycoside,carbo-glycoside,etc. according to the consecutive atomic type of glycoconjugate and carbon atom in saccharide ring.. Glycoside which is not been especial descripted usually is oxo-glycoside which is the most frequent and the glycoside in this article is also oxo-glycoside. The glycoside which glycoconjugate is carboxylic acid is called ester.Salidroside which can clean up free radical effectively protected free radical damage caused by ionising radiation markedly. Under normal circumstances, the production and elimination of free radical in vivo occupy the dynamic equilibrium state because of the consummate scavenging system of free radical in organism. Free radical can not be eliminated in time when free radical augmentated caused by fatigue stress, movement stress, and ionizing radiation. Free radical which has vivid chemical property not only changed the thecal structure and function but also induced increasing of lipid peroxidation product. It can induce the severe damage of internal organs such as skeletal muscle, articulation, brain, kidney, and lungs, etc., digestive system, and immune system, and one step further induced many kinds of disease. It can be seen that the elimination of free radical is one of the mechanism in common of antiradiation, antifatigue, and antihypoxic. It was reported that the introduction and position of hydroxy in benzene ring, the length of carbon chain between benzene ring and saccharide, and the type of linked saccharide can influence the capability of eliminating free radical. Among the total, the substituent of hydroxy can reinforce the action of antioxygen free radical and the influence of saccharide group to the elimination of free radical is also comparatively large, especially of the glycoside of galactose. In this study, we used galactose instead of glucose to create a firenew synthetic route of salidroside, at the mean while, we used resveratrol which has the capability personally as raw material to synthesis new compound through the reaction of asymmetry double hydroxylation and glycosidation to make the new compound not only keep the basic skeleton structure of salidroside but also increase the number of active hydroxy which has the ability to eliminate free radical, and even the most important thing is the introduction of two chiral carbon to be beneficial for investigating the solid structure-function relationship to obtain the compound which pharmacodynamic action is better than salidroside.Rosavidine which belonged to glycoside is also one of the main active ingredient in Gold Theragran. In this study, we used cinnamic acid, methyl cinnamate, methoxy group cinnamic acid, and ferulaic acid as raw materials to synthesis a series of glycoside compound on account of the precursor structure of Rosavidine.Human body was able to select chiral medicine precisely, l-isomer and d-isomer of chiral medicine not only their activity are different but also their effect were contradistinction at times , thus in this study , double bond of methoxy cinnamic acid, ferulaic acid were reformed so that chiral groups were inducted to investigate influences of different substituting groups and chirality to bioactivities of compounds.The papers can be divided into the following parts :1, a new method was designed to synthesis rhodioside (A1) and its analogue , galactoside(A2).2, Rosavidine was used as lead compound, cinnamic acid, methyl cinnamate, methoxy group cinnamic acid, and ferulaic acid were used as raw materials to synthesis a series of analogues(B1-B5).At the same time , we investigated influences of different substituting groups to bioactivities of compounds.3, chiral compounds(C1-C2) were designed and synthetized.4, in third process,two kinds of chiral catalysts were synthetized(D1-D2).5, synthesis of glyc- ester(E1-E2).A new type bifunctional compound can be obtained that is owning novel structure, high performance but harmfulless anti-fatigue anti-oxygen deficiency,antiradiation ,meanwhile,which offered a new way to treatment of radiation breakdown and fatigue.