Synthesis,Characterization And Performance Of 1,3,5-Trisubstitued-1H-Pyrazole And Pyrazolone

Polysubstituted pyrazoles and pyrazolones are important structural units that make up some bioactive molecules and organic synthesis,it have been widely used in the fields of medicine and functional materials.The compounds of 1,3,5-trisubstituted-l H-pyrazole are important,it is an integral part of multiple types of drug molecules,as the same time,pyrazole derivatives have a blue-violet fluorescence,some derivatives can be used as a fluorescent probe to detect metal ions,and have good stability.In recent years,pyrazolinones have been widespread used in the fields of synthetic materials,fluorescent probes and biological activities.The synthesis and optical properties of novel compounds have become hotspots of chemical researchers.Therefore,to design and synthesis of 1,3,5-trisubstituted-1H-pyrazole compounds,explore its optical properties and biological activity has great significance and application value.Based on our preliminary work,to design 2-hydrazino-5-substituted-1,3,4-thiadiazole as raw material respectively reacted with ethyl acetoacetate,ethyl 2-chloroacetoacetate and acetylacetone,22 target compounds were synthesized,of which 21 were completely new compounds.The structures of the target compounds were characterized by IR,¹H NMR,¹³C NMR and elemental analysis.With N,N-dimethyl formamide as solvent,by solution crystallization get the organic single-crystal of 4i and X-ray diffraction of the resulting organic single crystal structure test,further demonstrating the correctness structure of the synthesized target compound.The properties of UV and fluorescence with the synthesized compounds,the UV showed that of all the compounds have similar absorption peaks at 320 nm,because of the compounds have same nuclei,and have litter affect on the substituents of the benzene.Fluorescence spectra showed that all compounds exhibited purple fluorescence,while compounds 4c and 5c had a significant quenching effect on Cu²⁺and had no interference from other metal ions,so had a good selectivity for Cu²⁺.The fluorescence quenching efficiency of compound 4c was84 times,and compound 5c was 67 times.Compared with compounds 4c and 5c,compound4c has a detection limit of 3.4×10^-6M for Cu²⁺,which reached the requirement of probe.The study provides valuable reference for future use of these compounds as fluorescence probes for the detection for Cu²⁺.Determination Act 96 at a certain concentration gradient,against melanoma A375 cells and Hela cells of target compounds were synthesized anti-tumor cell activity test in vitro.The results indicated that several of these compounds were screened for their ability to inhibit 2different human tumor cell lines,and against Hela cells was better than against melanoma A375 cells.The compounds 4e have good antitumor activity,especially compound 4e displayed the most potent activity,with half of the cell proliferation was inhibited,it IC₅₀values of 1.8mg/m L and 0.65mg/m L against melanoma A375 cells and Hela cells lines,respectively.