Synthesis And Properties Of Novel 2-Ferrocenyl-4-methyl-1,3-selenazole-5-formyl Hydrazone Derivatives And Cu(?) Complexes

The synthesis of acylhydrazone heterocyclic compounds and acylhydrazone metal complexes and their application in medicine,pesticide and materials were reviewed.Fifteen2-ferrocenly-1,3-selenazole acylhydrazone were first designed and synthesized.Their structures were characterized through IR,NMR and HRMS.The inhibitation activities of the fifiteen molecules against PTP1B and Cdc25B were evaluated.Five Cu(II)complexes were synthesized by the reaction of five representative target molecules with Cu²⁺and their structures were characterized by IR,UV-Vis,fluorescence spectra and NMR.The fluorescent recognition of the complexes on CT-DNA and their interaction were performed using UV-Vis and fluorescence spectra.The specific content is as follow:1.Based on the excellent bioactivities of acylhydrazone,ferroceen and 1,3-selenazole,fifiteen target molecules 2-ferrocenyl-3-methoxy-1,3-seleazole acylhydrazones(Fc-SAH 1-15)were first synthesized using 1,3-selenazole as template.First,the hydrazide(Fc-SH)was afforded through esterification and hydrazinization.And then Fc-SH reacted with different aromatic aldehydes to form the target molecules successfully.The strntures of the target compounds were characterized by IR,NMR and HRMS.The yields of the target compounds were between 35%-85%.2.The inhibitory activities of Fc-SAH 1-15 against PTP1B and Cdc25B were first screened.As a result,15 compounds all showed good inhibitory activities against PTP1B and Cdc25B,in which 14 target compounds showed better inhibitory activities than the reference oleanolic acid(IC₅₀=1.30±0.00?g/m L).The IC₅₀values??of 14 target molecules were lower than the reference Na₃VO₄(IC₅₀=1.86±0.24?g/m L).These results indicate that the novel structural nolecules may be used as inhibitors of PTP1B and Cdc25B.3.Fc-SAH-2,Fc-SAH-9,Fc-SAH-10,Fc-SAH-11 and Fc-SAH-13 were selected as ligands and reacted with Cu(CH₃COO)₂·2H₂O respectively to yield five novel Cu(II)complexes.Their structures were confirmed by IR,UV-Vis,fluorescence spectra and NMR.The results show that the monodentate complexes are successfully prepared.4.The interaction mode between the Cu(II)complex and CT-DNA was studied using UV-Vis and fluorescence spectra.The interaction between complexes and CT-DNA result in absorption peak enhance and red-shift in UV-Vis spectra.The fluorescence spectra show that when the concentration of the complexes is invariable,the absorption peak is increased with the increase of the concentration of CT-DNA.When the concentration of EB-DNA is fixed,the fluorescence intensity of EB-DNA system is decreased with the increase of the concentration of the complex.The binding constant of complex and CT-DNA reach to10⁵order,which indicates that the complex and CT-DNA happen the optimum action through insertion mode.The result show that the complexes may be used in the disease monitoring and treatment.The novle Cu(II)complexes may be used as DNA molecular fluorescent prob.