Synthesis,Performance And Application Of The Novel Triazine Derivatives

Compounds containing 1,2,4-triazine or 1,3,5-triazine skeleton have a wide range of biological activities,particularly in anti-bacterial,anti-viral,anti-inflammatory and anti-cancer.Such compounds also have herbicidal and plant growth regulating activities.The derivatives which have 1,10-phenanthroline skeleton have potential applications in optoelectronics,catalysis,DNA nucleic acid probe.1.Forty target molecules of two series were designed and synthesized for the first time through simple and efficient methods.（1）Twenty new triazine derivatives（DAPT 1-10 and SAPT 1-10）were first synthesized using 3-amino-5,6-diphenyl-1,2,4-triazine（ADPT）and1,3,5-triazine derivatives（SAT and DAT）as starting materials,which l,3,5-triazine and1,2,4-trichlorobenzene triazine skeleton were combined through the imine bridge,and the overall isolated yield were 53.2%-81.3%,（2）Aromatic nitrile（BZT）was synthesized using aromatic aldehydes as starting material.Aromatic amino hydrazone derivatives（AMDZ）were then afforded by reaction BZT with hydrazine hydrate.Twenty 1,2,4-triazine skeleton phenanthroline derivatives（ARTP 1-20）were finally synthesized by nucleophilic addition-elimination reaction of AMDZ with phenanthroline dione,the overall isolated yield were 43.5%-68.4%.In this paper,101 target compounds were synthesized,including 61intermediates and the structures of all new compounds were characterized by IR and ¹H NMR etc.2.In order to study the interaction between the metal complexes with DNA,the target molecules ARTP-7、ARTP-8 and ARTP-17 were selected as the ligands and coordinated with Co³⁺and Ni²⁺,respectively to afford 6 kinds of new metal complexes which were characterized by melting point,IR,UV and ¹H NMR.3.The plant growth regulatory activities and herbicidal activity of the 40 kinds of target molecules were studied through classic reliable methods.The results showed that the two series of the target products exhibited excellent cell division activity,almost all the compounds exhibited better promoting activities,up to grade A,in which ARTP-19 reached as high as 89.3%.In the activity of auxin tests,DAPT-7,DAPT-10,SAPT-7 and ARTP-19showed inhibition effect of B grade.In the herbicidal activity tests,DAPT-8,DAPT-9,DAPT-10,SAPT-10,ARTP-17,ARTP-18 and ARTP-19 exhibited excellent herbicidal activity,the inhibition rates were above 91.0%,which might be an excellent herbicide.4.The inhibitory activities of the target products against PTP1B and Cdc25B were first performed.The results showed that:DAPT-2,DAPT-10 and SAPT-10 showed better inhibitory activities to PTP1B,especially the molecule SAPT-10(IC₅₀=1.15±0.30μg/m L),which was better than the contrast oleanolic acid(IC₅₀=1.27±0.19μg/mL);DAPT-1,DAPT-2,DAPT-4,DAPT-7,SAPT-7,SAPT-9,SAPT-10,ARTP-1,ARTP-7,ARTP-8,ARTP-17 and ARTP-19 showed certain antitumor inhibitory effect against Cdc25B,SAPT-10(IC₅₀=0.19±0.05μg/mL)and ARTP-7(IC₅₀=0.39±0.02μg/mL)were superior to comparative inhibitory activity reference(sodium vanadate:IC₅₀=1.86±0.24μg/mL).As a result,the target molecule are expected to be potential inhibitors against PTP1B and Cdc25B.5.The interaction modes between the complexes and DNA were studied by UV-Vis spectra and fluorescent spectra.It was found that the excitation peaks of complexes happened a red shift;with the increasing of the concentration of DNA,the fluorescence intensities weakened sharply.The fluorescence intensities of EB-DNA system were lower with the increasing of concentration of complexes,the orders of magnitude were up to10⁵.These results showed that our complexes interacted with CT-DNA through the insert mode,The better the co-planar properties of the ARTP-8 complexes are,the easier inserting way interaction and stronger combination are performed.