Synthesis, Characterization And Properties Of Novel Thiazole/Chalcone Derivatives Containing Carbazole Moiety

1.In this paper,thirty-two new compounds were designed and synthesized,including three new intermediate compounds 3a~3c,2-[(N-alkyl-carbazol-3-yl)methylidene]hydrazinyl carbothioamide,twenty-three new thiazole derivatives containing carbazole moiety TM-I-4a~4w,2-{2-[(N-alkyl-carbazol-3-yl)methylidene]hydrazinyl}-4-arylthiazole and six new chalcone derivatives containing carbazole moiety TM-II-3a~3f,(2E)-1-biphenyl-3-(N-alkyl-carbazol-3-yl)prop-2-ene-1-one.All the synthesized new compounds were confirmed from IR,1H NMR,13 C NMR,and elemental analysis.2.All new compounds were evaluated for their inhibitory activity against Cdc25 B and PTP1 B.The experimental results were as follows.(1)The target compounds TM-I-4a~4w(except 4b)and their intermediates 3a~3c displayed high inhibitory activity against Cdc25 B.Among them,compound 4q had the highest inhibitory activity with IC50=(0.30 ± 0.03)μg/m L.Except compounds 3c and 4t,they also had high inhibitory activity against PTP1 B,and compound 4e had the highest inhibitory activity,IC50=(1.85 ± 0.19)μg/m L.(2)The target compounds TM-II-3a~3f showed high inhibitory activity against Cdc25 B,and the inhibition rates were from 97.36% to 98.11%.Among them,the target compound 3e had the best inhibitory activity with IC50=(0.97 ± 0.07)μg/m L.Some of the target compounds had inhibitory activity against PTP1 B,and the compound 3a had the highest inhibitory activity with IC50=(1.53 ± 0.32)μg/m L.3.The thermal,optical and electrical properties of target compounds TM-II-3a~3f were investigated.The results showed that these compounds had good thermal stability(T5d > 384 ℃)and electrochemical stability(no reduction peaks).The solid target compounds obtained from ethyl acetate emitted fluorescence from blue to yellow under the ultraviolet lamp.The target compounds in DMSO emitted green fluorescence under the ultraviolet lamp.Photoluminescence spectra showed that the emission bands were at 515~516 nm.They had large stokes shifts(114~115 nm)and high fluorescence quantum yields((37)F=0.63~0.88).The target compounds TM-II-3 have potential application value in optical materials.4.The obtained results in this thesis provide a scientific basis for the development of novel Cdc25B/PTP1 B inhibitors and organic small molecule optical materials.The research of this thesis has important significance.