Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363

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Synthesis, structure activity relationship and anti-influenza A virus evaluation of oleanolic acid-linear amino derivatives
Weijia LiFan YangLingkuan MengJiaqi SunYangqing SuLiang ShaoDemin ZhouFei Yu
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JOURNAL FREE ACCESS Advance online publication

Article ID: c19-00485

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Abstract

Oleanolic acid (OA) was discovered as a mild influenza hemagglutinin (HA) inhibitor in our earlier studies. In the present work, 20 compounds were prepared by structural modifications of OA, and their antiviral activities against influenza A/WSN/33 (H1N1) virus in MDCK cells were evaluated. Based on the biological result, structure–activity relationship (SAR) was discussed. Compound 10 with six-carbon chain and a terminal hydroxyl group showed the strongest anti-influenza activity with an IC50 of 2.98 μM, which is an order of magnitude more potent than OA. Hemagglutination inhibition and Surface plasmon resonance (SPR) assay indicated that compound 10 might interfere with influenza invasion by interacting with HA protein.

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© 2019 The Pharmaceutical Society of Japan
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