Design, synthesis and cytotoxic activities of fluorine-containing 2, 5-diketopiperazine derivatives

TANG Yong; LIAO Shengrong; LI Jinsheng; LIU Yonghong

doi:10.11665/j.issn.1000-5048.20160405

Journal of China Pharmaceutical University > 2016 > 47(4): 412-421. > DOI: 10.11665/j.issn.1000-5048.20160405

TANG Yong, LIAO Shengrong, LI Jinsheng, LIU Yonghong. Design, synthesis and cytotoxic activities of fluorine-containing 2, 5-diketopiperazine derivatives[J]. Journal of China Pharmaceutical University, 2016, 47(4): 412-421. DOI: 10.11665/j.issn.1000-5048.20160405

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Design, synthesis and cytotoxic activities of fluorine-containing 2, 5-diketopiperazine derivatives

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Twenty-one novel fluorine-containing 2, 5-diketopiperazine derivatives( 2a - 2u )were synthesized by using N, N-diacetyl-2, 5-diketopiperazine, allylbromide, 2-fluorobenzaldehyde and other aromatic aldehydes. The structures were characterized by ¹H NMR, ¹³C NMR, and HRMS. The cytotoxicities were evaluated against ten human tumour cell lines(K562, U937, MOLT-4, HL60, HeLa, DU145, MCF-7, A549, SGC-7901, H1975)by using CCK8 assay. Results showed that compounds 2a , 2d , 2e , 2f , 2g , 2h , 2k , and 2t showed significant cytotoxicity against U937(IC₅₀=0. 2 μmol/L), HeLa(IC₅₀=0. 5 μmol/L), and DU145(IC₅₀=0. 7 μmol/L), respectively. Compound 2t could become a lead compound for further development for anticancer agents.
- 2,5-diketopiperazine derivative,
- fluorine-containing,
- synthesis,
- cytotoxic activity

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