Synthesis And Application Of Indirunbin And Its Dderivatives

Indirubin, also called Couraupitine B, is China’s first anti-leukemia drugs. It consists ofthe two condensed indole rings, the entire molecule is V-shaped. The structure of indirubinis different from indigo with two hydrogen bonds, its carbonyl oxygen atom on another indolring is exposed outside due to the hydrogen bond is not formed, thus providing the bindingsites between the cancer cells with DNA. Because its skeleton is similar to the purinealkaloids, So they can occur with the π-π complexation to form molecular compounds. Thisblocks the synthesis of DNA of tumor cells fundamentally, and thus exert an anti-cancereffect. However, due to high melting point of indirubin and its lipophilic or hydrophilic ispoor, so speculate that this may be related to the formation of hydrogen bond and thearrangement of crystals in intramolecular or intermolecular, thus start the research ofindirubin derivatives.The thesis mainly includes:1）Using chloroform and ethyl acetate as the eluent,40%of crude indirubin was purifiedby column chromatography. after the second elution and dried to give purple solid. The use ofIR,1HNMR, HRMS structural characterization was carried out, indicating that extracts asingle component, high purity.2）Indirubin with hydroxylamine hydrochloride and potassium hydroxide as raw materialsynthesized Indirubin oxime, in the presence of a solvent the indirubin is reacted with acetylchloride to obtain N-acetyl indirubin. The structure of two compounds were characterized byMS.UV and scence properties were measured and found Indirubin after acetylation, since theintroduction of the carbonyl group, the N-acetyl indirubin has good fluorescence properties, isa novel fluorescent probe.3）Using N-acetyl indirubin as fluorescent probe, the cationic surfactant D1821, anionicsurfactant SDS, zwitterionic surfactant BS-12CMC were measured, results consistent withliterature values.4）Using N-acetyl indirubin as fluorescent probe, through the study on the interaction withDNA and found that the mode of action of N-acetylidirubin and DNA is a static quenchingprocedure.