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Mar. Drugs 2011, 9(10), 1887-1901; doi:10.3390/md9101887

Studies on Synthesis and Structure-Activity Relationship (SAR) of Derivatives of a New Natural Product from Marine Fungi as Inhibitors of Influenza Virus Neuraminidase

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School of Chemistry and Chemical Engineering, Sun Yat-Sen University, Guangzhou 510275, China
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Guangdong Province Key Laboratory of Functional Molecules in Oceanic Microorganism, Bureau of Education, Sun Yat-sen University, Guangzhou 510080, China
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Key Laboratory of Tropical Disease Control, Ministry of Education, Sun Yat-sen University, 74 Zhongshan Road II, Guangzhou 510080, China
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Department of Microbiology, Zhongshan School of Medicine, Sun Yat-sen University, 74 Zhongshan Road II, Guangzhou 510080, China
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Department of Anatomy, Zhongshan School of Medicine, Sun Yat-sen University, 74 Zhongshan Road II, Guangzhou 510080, China
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Authors to whom correspondence should be addressed.
Received: 2 September 2011 / Revised: 26 September 2011 / Accepted: 30 September 2011 / Published: 11 October 2011
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Abstract

Based on the natural isoprenyl phenyl ether from a mangrove-derived fungus, 32 analogues were synthesized and evaluated for inhibitory activity against influenza H1N1 neuraminidase. Compound 15 (3-(allyloxy)-4-hydroxybenzaldehyde) exhibited the most potent inhibitory activity, with IC50 values of 26.96 μM for A/GuangdongSB/01/2009 (H1N1), 27.73 μM for A/Guangdong/03/2009 (H1N1), and 25.13 μM for A/Guangdong/05/2009 (H1N1), respectively, which is stronger than the benzoic acid derivatives (~mM level). These are a new kind of non-nitrogenous aromatic ether Neuraminidase (NA) inhibitors. Their structures are simple and the synthesis routes are not complex. The structure-activity relationship (SAR) analysis revealed that the aryl aldehyde and unsubstituted hydroxyl were important to NA inhibitory activities. Molecular docking studies were carried out to explain the SAR of the compounds, and provided valuable information for further structure modification.
Keywords: aromatic ether; marine fungus; neuraminidase inhibitor aromatic ether; marine fungus; neuraminidase inhibitor
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MDPI and ACS Style

Li, J.; Zhang, D.; Zhu, X.; He, Z.; Liu, S.; Li, M.; Pang, J.; Lin, Y. Studies on Synthesis and Structure-Activity Relationship (SAR) of Derivatives of a New Natural Product from Marine Fungi as Inhibitors of Influenza Virus Neuraminidase. Mar. Drugs 2011, 9, 1887-1901.

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