Synthesis Of Tanshinone ?A Deriviatives

Salvia miltiorrhiza Bunge is a common perennial herb and distributes in most parts of China.It has a high medicinal value.The root of Salvia miltiorrhiza is mainly used in the treatment of coronary heart diseases.The leaves of Salvia miltiorrhiza are mainly used for flat wart.The main active ingredients of Salvia miltiorrhiza are water-soluble and liposoluble components.Tanshinone ?A is a lipophilic component of traditional Chinese medicine Salvia miltiorrhiza.It has various physiological activities such as anti-tumor,anti-oxidation,anti-cardiovascular and cerebrovascular diseases.In this thesis I have designed and synthesized a series of derivatives via structural modification of tanshinone ?A in order to obtain compounds with better activity,as structural modification is necessary due to its low activity.???A Vilsmeier reaction of tanshinone ?A was developed to provide an intermediate with an aldehyde substituent at its 16-position.A 16-aminomethyl substituted tanshinone ?A derivative was then obtained in high yield via a reductive amination reaction of the above mentioned intermediate with ammonium acetate.After modification of the amino group,13 tanshinone ?A derivatives bearing different N-substituents were obtained.The optimal reaction conditions were determined as follows:in 1,2-dichloroethane under 40?for 2 hours,n?intermediate 2?:n?sodium borohydride acetic acid?=1:2,intermediate 2was transformed into the optimal reaction conditions of the intermediate 3.Conclusion:Structures of all the desired products were confirmed by ¹H NMR,¹³C NMR and LC-MS analysis.The research work of this paper provides a simple and efficient method for the synthesis of tanshinone ?A derivatives.