The Synthesis Of Bithiazolyl-hydrazone And The Research Of Their Properties

Bithiazole and its derivatives were widely used for photolectric material,interaction with DNA binding,organic magnetic material and so on due to their large ?-conjugated aromatic heterocyclic system,good bidentate-dentate chelating ability and electron-transport properties.Hydrazones constitute a class of compounds presenting azomethine R-C=N-N-R hydrogens,which have been the subject of investigations due to their modularity and unique structural features,properties and a wide range of applications in the field of agriculture,pharmaceuticals and functional materials.It is significant to study the compounds containing bithiazolyl-hydrazone derivatives for the concentration properties on the optics,sensors,and medicine.Herein,we synthesized 15 novel kinds of bithiazolyl-hydrazone compounds,and further studied their optical properties and biological activities.1.Fifteen kinds of bithiazolyl-hydrazone compounds were synthesized by Hantzsch condensation reaction,using 2,3-butanedione,bromine,thiosemicarbazide and different kinds of benzaldehyde as raw materials.These compounds were characterized by 1H NMR,13 C NMR,MS,elemental analysis,IR.Fortunately,the single crystal structures of BhL₁,BhL6 were obtained.2.The UV absorption spectrum in the range of 258-359 nm were attributed to ?-?* type of transitions in the molecular.It showed that all the compounds have strong fluorescent emission features.Halogen substituents of aromatic ring exihibited a bathochromic shift of the absorption as well as emission bands.Quantum chemistry calculations of these compounds were carried in order to further explain the optical properties.3.BhL₁^BhL₁₅ were selectively sensed mental ions Fe³⁺ with significant decrement of emission intensity.Notablely,it could be easily observed that the BhL₁₅ changed from colourless to yellow by the naked eye,when Cu²⁺ were dropped in.BhL₁₅ showed high selectivity and excellent anti-disturbance ability towards Cu²⁺.It was tested that the complex ratios of BhL₁₅-Cu²⁺ were 1:1 by Job Plot.And the limits of detection were 3.74 mM.4.The antibacterial activity tests indicated that 3-chlorinated and 3-hydroxylnated bithiazolyl-hydrazone derivatives?BhL8,BhL₁0?display significant activity against gram positive bacteria.These compounds showed different activities against different human cancer cells.BhL5 exhibited good inhibition against Human esophageal cancer cells EC-9706?IC50=11.76 mM?.The target compounds with meta substitution were more activity than that of para,ortho.Compound with 3-chlorinated?BhL8?substituted excelled in the anticancer activity.