Synthesis of Dithiacrown Ethers and Evaluation of Their Cytotoxic Activity. Issue 40 (26th October 2021)

• Record Type: Journal Article
• Authors: Dao, N. T.; Nguyen, D. T.; Nguyen, L. M.; Tran, V. T. T.; Do, T. T.; Le, A. T.
• Is Part Of: ChemistrySelect. Volume 6:Issue 40(2021)
• Page Start: 11081
• Page End: 11085
• Publication Date: 2021-10-26
• Subjects: Cytotoxicity -- Domino reaction -- Piperidone -- Tetrahydropyridine -- Thiacrown ethers; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202102963
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: 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, 1 H & 13 C‐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. Abstract : New dithiacrown ethers containing piperidone ring were synthesized base on the one‐pot Petrenko‐Krischenko reaction. Howerver, the condensation from benzyl acetoacetate in the reaction media afforded unexpected dithiacrown ether bearing 4‐aminotetrahedropyridine moiety. The cytotoxicity on human cancer cells of the synthesized compounds was studied.