Synthesis and anti-influenza activity of aminoalkyl rupestonates

Bioorganic & Medicinal Chemistry Letters
Jiangyu Zhao, Haji Akber Aisa

Abstract

A series of aminoalkyl rupestonates were designed and synthesized by reacting rupestonic acid with 1,ω-dibromoalkanes, followed by amination. All of the new compounds were bioassayed in vitro to determine their activities against influenza A (H3N2, H1N1) and B viruses. The results showed that compounds 5a-5g, which each contain a 1H-1,2,4-triazolyl moiety, were found to be the most potent set of compounds. Compound 5g was demonstrated to possess the highest inhibitory activity against influenza H3N2 and H1N1, with IC(50) values of 0.97 and 0.42 μM, respectively. Our results also indicated that compounds 2g, 3g, 4g and 5g, which contain ten-CH(2)-unit spacers between the rupestonic acid and amino functional groups, were the most potent inhibitors of influenza H1N1 among the synthesized compounds. Unfortunately, most of the synthesized compounds did not show an obvious activity against influenza B; the only exceptions were compounds 5d and 5f, which had IC(50) values of 17.3 and 3.2 μM, respectively. Compounds 4g and 5g were potent inhibitors of influenza H1N1, and they might be potentially developed as new lead anti-influenza virus compounds. Further studies of the mechanism of action are underway.

References

Oct 18, 2005·Nature·Q Mai LeYoshihiro Kawaoka

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Citations

Dec 24, 2015·Journal of Natural Products·Chen ZhangPeng-Fei Tu
Apr 22, 2016·Chemical Reviews·Svilen P SimeonovCarlos A M Afonso
Aug 1, 2012·Current Opinion in Virology·Erik De Clercq
Apr 4, 2017·Bioorganic & Medicinal Chemistry Letters·Oleg I ArtyushinValery K Brel
Jul 18, 2020·Medicinal Research Reviews·Zhi-Jun ZhangRong-Tao Li
Jan 20, 2020·Acta Pharmaceutica : a Quarterly Journal of Croatian Pharmaceutical Society and Slovenian Pharmaceutical Society, Dealing with All Branches of Pharmacy and Allied Sciences·Nashwa Hafez ZaherAbdullah Yousef Altaher
Apr 29, 2021·Results in Chemistry·Insa Seck, Filomain Nguemo
Dec 7, 2017·Organic Letters·Pan HanGuo-Qiang Lin

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