Design,Synthesis And Preliminary Antitumor Activity Of Adamantane Schiff Base Derivatives

Adamantane,molecular formula C10H16,is a cage compound with good symmetry and rigid structure.Its molecular structure is similar to the carbon skeleton structure of diamond lattice unit.Adamantane has unique physical and chemical properties,its water solubility is poor,but the lipid solubility is good,has good lipophilic,can be slightly soluble in benzene,tasteless,easy to sublimate.The unique physical and chemical properties of adamantane make it widely used in drugs with some special curative effects.The pharmacological effects of adamantane are antiviral,antidepressant,and antitumor.Applications in drug carrying agent,based on the adamantane compounds fat-soluble strong characteristic,can be king kong alkyl group access to effective drug molecules,known by flow across the membrane to affect ion channels,improve drug molecules across the cell membrane,change the body to a drug absorption,distribution,metabolism and excretion process,make the drug works better.Adamantane compounds have the characteristics of excellent thermal stability and good fat solubility.By combining them with the special structures of Schiff bases and their complexes into a structural system,new compounds with novel structures and unique properties are expected to be obtained.Using 1-bromoadamantane as the starting material,an important intermediate 4 was obtained through atypical Friedel-Crafts alkylation reaction,radical substitution and oxidation reaction,and finally the intermediate 4adamantane benzaldehyde and the aniline underwent condensation reaction to obtain Schiff base derivatives 5a-f.The structure was characterized by nuclear magnetic resonance,infrared and mass spectrometry.Preliminary prediction of drug-like and pharmacokinetic properties of the synthesized compounds by ADMET predictor.The effect of synthetic small molecules on the proliferation of cancer cells A549,He La,MCF-7 and normal cells HEK-293 was evaluated using CCK-8 cytotoxicity assay.The results showed that compound 5e had a good anti-proliferative effect on human lung cancer cell A549,and all small molecules had no toxicity to normal cell HEK-293.