2,5-Diketopiperazine Derivatives as Potential Anti-Influenza (H5N2) Agents: Synthesis,Biological Evaluation,and Molecular Docking Study |
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| Authors: | Chanakan Winyakul Weerachai Phutdhawong Poomipat Tamdee Jitnapa Sirirak Thongchai Taechowisan Waya S. Phutdhawong |
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| Affiliation: | 1.Department of Chemistry, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand; (C.W.); (P.T.); (J.S.);2.Department of Chemistry, Faculty of Liberal Arts and Science, Kasetsart University, Kamphaengsaen Campus, Nakorn Pathom 73140, Thailand;3.Department of Microbiology, Faculty of Science, Silpakorn University, Nakorn Pathom 73000, Thailand; |
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| Abstract: | 2,5-Diketopiperazine derivatives, consisting of benzylidene and alkylidene substituents at 3 and 6 positions, have been considered as a core structure for their antiviral activities. Herein, the novel N-substituted 2,5-Diketopiperazine derivatives were successfully prepared and their antiviral activities against influenza virus were evaluated by monitoring viral propagation in embryonated chicken eggs. It was found that (3Z,6Z)-3-benzylidene-6-(2-methyl propylidene)-4-substituted-2,5-Diketopiperazines (13b–d), (3Z,6E)-3-benzylidene-6-(2-methylpropyli dene)-1-(1-ethyl pyrrolidine)-2,5-Diketopiperazine (14c), and Lansai-C exhibited negative results in influenza virus propagation at a concentration of 25 µg/mL. Additionally, molecular docking study revealed that 13b–d and 14c bound in 430-cavity of neuraminidase from H5N2 avian influenza virus and the synthesized derivatives also strongly interacted with the key amino acid residues, including Arg371, Pro326, Ile427, and Thr439. |
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| Keywords: | 2,5-Diketopiperazines antiviral activity influenza virus molecular docking Lansai C Lansai D |
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