Synthesis of Dithiacrown Ethers and Evaluation of Their Cytotoxic Activity

摘要

New derivatives of thiacrown ethers were synthesized based on the domino reaction of 1,5-bis(2-formylphenthio)-3-oxapentane with ketones containing active methylene group and ammonium acetate. After 24 hours at moderate temperature, the reaction afforded new substances containing both polyether chain S(CH2)(2)-O-(CH2)(2)-S and heterocyclic piperidone. Particularly when benzyl acetoacetate was used, the three - component reaction provided a final tetrahydropyridine derivative product containing enamine fragment instead of piperidone as expected. Physico-chemical methods of analyses including IR, H-1 &C-13-NMR and HRMS were used to clarify these structures. Subsequently, the cytotoxicity of five novel derivatives were evaluated on four cancer cells including HeLa (HeLa cervical cancer), Hep-G2 (human hepatocellular carcinoma), MCF7 (human breast adenocarcinoma), Lu-1 (human lung adenocarcinoma) and Vero cell. The result showed the potential application of these compounds in terms of biological activity.