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Bioorg Med Chem. 2014 Dec 15;22(24):6826-36. doi: 10.1016/j.bmc.2014.10.033. Epub 2014 Oct 31.
Novel derivatives of usnic acid effectively inhibiting reproduction of influenza A virus.
Shtro AA1, Zarubaev VV2, Luzina OA3, Sokolov DN3, Kiselev OI1, Salakhutdinov NF3.
Author information
Abstract
Influenza virus is serious human pathogen leading to high morbidity and mortality all over the world. Due to high rate of mutation, it is able to fast development of drug resistance that makes necessary to search novel antivirals with broad range and alternative targets. In the present study we describe synthesis and anti-viral activity of novel derivatives of usnic acid (2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzo-furandione). It is shown that anti-viral activity of usnic acid can be increased by side moieties introduction. The modification with chalcones appeared to be the most effective. Our study revealed that (-)-usnic acid exhibited higher antiviral activity than its (+)-enantiomer, but in the pairs of enantiomer derivatives such as enamines, pyrazoles and chalcones, the (+)-enantiomers were more potent inhibitors of the virus. For other groups of compounds the inhibiting activities of the enantiomers were comparable. Further optimization of the structure could therefore result in development of novel anti-influenza compound with alternative target and mechanism of virus-inhibiting action.
Copyright ? 2014 Elsevier Ltd. All rights reserved.
KEYWORDS:
Anti-viral activity; Influenza; Usnic acid; Usnic acid derivatives
PMID:
25464881
[PubMed - in process]
Novel derivatives of usnic acid effectively inhibiting reproduction of influenza A virus.
Shtro AA1, Zarubaev VV2, Luzina OA3, Sokolov DN3, Kiselev OI1, Salakhutdinov NF3.
Author information
Abstract
Influenza virus is serious human pathogen leading to high morbidity and mortality all over the world. Due to high rate of mutation, it is able to fast development of drug resistance that makes necessary to search novel antivirals with broad range and alternative targets. In the present study we describe synthesis and anti-viral activity of novel derivatives of usnic acid (2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzo-furandione). It is shown that anti-viral activity of usnic acid can be increased by side moieties introduction. The modification with chalcones appeared to be the most effective. Our study revealed that (-)-usnic acid exhibited higher antiviral activity than its (+)-enantiomer, but in the pairs of enantiomer derivatives such as enamines, pyrazoles and chalcones, the (+)-enantiomers were more potent inhibitors of the virus. For other groups of compounds the inhibiting activities of the enantiomers were comparable. Further optimization of the structure could therefore result in development of novel anti-influenza compound with alternative target and mechanism of virus-inhibiting action.
Copyright ? 2014 Elsevier Ltd. All rights reserved.
KEYWORDS:
Anti-viral activity; Influenza; Usnic acid; Usnic acid derivatives
PMID:
25464881
[PubMed - in process]
