Preparation And Characterization Of Houttuynine Derivatives And Their Copper Complexes

Houttuynia cordata is an important herb that has been widely used as an anti-inflammatory,antiviral and antibacterial agent in China for many years.Houttuylin is the main component of the volatile oil of Houttuynia cordata.The chemical properties of houttuynia houttuyniae compounds are unstable and their water solubility is poor.Therefore,its addition product sodium houttuyfonate?12-C?and its homologue new houttuyfonate sodium?14-C?and sodium oxy acetaldehyde sulfite?10-C?were used to replace it in practical application.In clinical application,12-C and 14-C have been used to treat suppurative skin infections,respiratory infections and so on.Studies have shown that,within a certain range,the stronger the lipid solubility of the groups attached to the carbon chain of houttuynia houttuyniae compounds,the better their biological activities in vivo.In this paper,12-C and its homologues 10-C and 14-C are used as raw materials.Chemical modification was carried out on the basis of preserving the active group carbonyl of the raw material.The aim of this paper is to obtain novel compounds with higher or wider biological activity.The main work of the thesis:1.Chemical modification of houttuynia houttuyniae compounds in the form of covalent bonds was carried out to change the lipid solubility of houttuyniae houttuyniae.Using 10-C,12-C and 14-C as starting materials,9 schiff bases were synthesized by reaction with ethylenediamine,1,4-butanediamine,aniline and 4-aminoantipyrine respectively,and their structures were characterized by IR,UV,NMR and elemental analysis,and Their structures were determined as C₁₆H₂₃ON?L¹?,C₁₈H₂₇ON?L²?,C₂₀H₃₁ON?L³?,C₂₂H₄₀O₂N₂?L⁷?.C₂₆H₄₈O₂N₂?L⁸?,C₃₀H₅₆O₂N₂?L⁹?,C₂₄H₄₄O₂N₂(L¹⁰),C₂₈H₅₂O₂N₂(L¹¹),C₃₂H₆₀O₂N₂(L¹²).Schiff base L_I,L₂ and L₃ is single schiff base,the materials of houttuynia cordata were combined with aniline in a ratio of1:1.Schiff base L⁷,L⁸,L⁹,L¹⁰,L¹¹ and L¹² has a symmetric structure,the materials of houttuynia cordata is combined with 1,4-butanediamine and ethylenediamine in a ratio of 2:1.2.The copper complex has biological activities such as antibacterial and antitumor.Therefore,based on the synthesis of schiff base,this paper forms complexes with transition metal copper ions,expecting that the schiff base copper complexes will play a synergistic role.The schiff base L⁴(C₂₁H₂₉O₂N₃),L⁵(C₂₃H₃₃O₂N₃),L⁶(C₂₅H₃₇O₂N₃),L¹⁰,L¹¹ and L¹² were used as raw materials for coordination reaction with the transition metal copper salt?L⁴,L⁵ and L⁶ were prepared by Ye Xiaoyi?.Finally,six schiff base copper complexes were obtained.The structures of the six copper complexes were determined by means of IR,UV and elemental analysis,and their structures were determined as Cu?L⁴?₂,Cu?L⁵?₂,Cu?L⁶?₂,Cu(L¹⁰),Cu(L¹¹)and Cu(L¹²).Cu?L⁴?₂,Cu?L⁵?₂ and Cu?L⁶?₂ were obtained by combining ligand and copper salt in a ratio of 2:1,while Cu(L¹⁰),Cu(L¹¹)and Cu(L¹²)were obtained by combining ligand and copper salt in a ratio of 1:1.3.Directly using 10-C,12-C and 12-C as ligands,respectively,reacted with the transition metal ions in a ratio of 2:1 to obtain the corresponding three copper complexes.The structure of the three copper complexes was determined by means of IR,UV,elemental analysis and single crystal diffraction.The structure of complex 1 is determined.Complex 1 takes Cu?II?as the center,forming a planar quadrilateral structure.The molecular formulas of complexes 1-3 are C₂₀H₃₄O₄Cu,C₂₄H₄₂O₄Cu,and C₂₈H₅₀O₄Cu,respectively.