國家衛生研究院 NHRI:Item 3990099045/1174
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    题名: Synthesis and antipicornavirus activity of (R)- and (S)-1-[5-(4 '-chlorobiphenyl-4-yloxy)-3-methylpentyl]-3-pyridin-4-yl-imidazolidin-2-one
    作者: Chern, JH;Chang, CS;Tai, CL;Lee, YC;Lee, CC;Kang, IJ;Lee, CY;Shih, SR
    贡献者: Division of Biotechnology and Pharmaceutical Research
    摘要: The new pyridyl imidazolidinone derivative, 1-[5-(4'-chlorobiphenyl-4-yloxy)-3-methylpentyl]-3-pyridin-4-yl-imidazolidin-2-one (+/-)-1a, was synthesized and found to have an excellent antiviral activity against EV71 (IC50 = 0.009 mu M). Therefore, both the enantiomers, (S)-(+)-1a and (R)-(-)-1a, have been prepared starting from readily available monomethyl (R)-3-methylglutarate (7) as a useful chiral building block and their antiviral activity was evaluated in a plaque reduction assay. Interestingly, we observed that the enantiomer (S)-(+)-1a was 10-fold more active against enterovirus71 (EV71) (IC50 = 0.003 mu M) than the corresponding enantiomer (R)-(-)-1a (IC50 = 0.033 mu M). Similar results were found against all five strains (1743, 2086, 2231, 4643, and BrCr) of EV71 tested. This demonstrated that the absolute configuration of the chiral carbon atom at the 3-position of the alkyl linker considerably influenced the anti-EV71 activity of these pyridyl imidazolidinones. (c) 2005 Elsevier Ltd. All rights reserved.
    关键词: Chemistry, Medicinal;Chemistry, Organic
    日期: 2005-10-01
    關聯: Bioorganic and Medicinal Chemistry Letters. 2005 Oct;15(19):4206-4211.
    Link to: http://dx.doi.org/10.1016/j.bmcl.2005.06.069
    JIF/Ranking 2023: http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=NHRI&SrcApp=NHRI_IR&KeyISSN=0960-894X&DestApp=IC2JCR
    Cited Times(WOS): https://www.webofscience.com/wos/woscc/full-record/WOS:000231663400009
    Cited Times(Scopus): http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=23944476628
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