The Synthesis Of Ferrocenyl-benzoyl-dipdptide And The Research Of Their Properties

Ferrocene and its derivative have a broad prospect of application in the filed of chemical, biological, medicine and so on due to its ease of derivatization, stability, spectroscopic properties and redox activity. Amino acids and peptides are widely applied in biology, medicine and so on due to their good biological activity. It’s very significant to design the compound of ferrocene- peptide linkage for the research of drug, the exploration of biological activity, as well as the application of the electrochemical properties. In this paper, we synthesized 13 kinds of ferrocenyl-benzoyl-dipdptide using ferrocene and different kinds of aminos as raw material. We also studied their electrochemical and biological activities.1. Thirteen new ferrocenyl-benzoyl-dipdptide were obtained by a series of reactions using the method of liquid-phase synthesis, with HBTU as condensing agent, ferrocene, p-aminobenzoic acid, m-aminobenzoic acid, m-aminobenzoic acid, L-glycine, valine, leucine, phenylalanine, serine and tyrosine as raw material. They were characterized by IR spectroscopy, 1H NMR, 13 C NMR and elemental analysis. 2. We studied their UV-vis spectral, electrochemical properties, the response to metal ions and biological activity. Gaussian process has been carried on the theoretical calculation to them in order to the further explanation their spectroscopy properties and electrical properties. 3. The electrochemical research of Fc L1~Fc L13 showed that the reaction on the surface of electrode were reversible with single electron, and they were controlled by diffusion of these thirteen new ferrocenyl-benzoyl-dipdptide compounds, which indicated that the electrochemical environment of ferrocenyl were very similar. They all have good response to copper ion. 4. Biological activity results showed that these 13 kinds of compounds have different activities to different cancer cells, indicating that the position of the substituents, and the size of the substituent have a certain degree of influence on the anticancer activity. The compound of Fc L3 showed the best inhibitive ablity to EC-109, Fc L1, Fc L2, Fc L5, Fc L7 and Fc L11 showed good inhibitive ablity to PC-3, when dipeptide side chain containing benzene ring, the inhibition rate of human prostate cancer cells PC-3 will be greatly reduced or even disappear.