Design, synthesis, and evaluation of trifluoromethyl ketones as inhibitors of SARS-CoV 3CL protease
Identifieur interne : 000E30 ( Pmc/Checkpoint ); précédent : 000E29; suivant : 000E31Design, synthesis, and evaluation of trifluoromethyl ketones as inhibitors of SARS-CoV 3CL protease
Auteurs : Yi-Ming Shao [Taïwan] ; Wen-Bin Yang [Taïwan] ; Tun-Hsun Kuo [Taïwan] ; Keng-Chang Tsai [Taïwan] ; Chun-Hung Lin [Taïwan] ; An-Suei Yang [Taïwan] ; Po-Huang Liang [Taïwan] ; Chi-Huey Wong [Taïwan, États-Unis]Source :
- Bioorganic & Medicinal Chemistry [ 0968-0896 ] ; 2008.
Abstract
Url:
DOI: 10.1016/j.bmc.2008.02.040
PubMed: 18329272
PubMed Central: 7127754
Affiliations:
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<front><journal-meta><journal-id journal-id-type="nlm-ta">Bioorg Med Chem</journal-id><journal-id journal-id-type="iso-abbrev">Bioorg. Med. Chem</journal-id><journal-title-group><journal-title>Bioorganic & Medicinal Chemistry</journal-title></journal-title-group><issn pub-type="ppub">0968-0896</issn><issn pub-type="epub">1464-3391</issn><publisher><publisher-name>Published by Elsevier Ltd.</publisher-name></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">18329272</article-id><article-id pub-id-type="pmc">7127754</article-id><article-id pub-id-type="publisher-id">S0968-0896(08)00161-2</article-id><article-id pub-id-type="doi">10.1016/j.bmc.2008.02.040</article-id><article-categories><subj-group subj-group-type="heading"><subject>Article</subject></subj-group></article-categories><title-group><article-title>Design, synthesis, and evaluation of trifluoromethyl ketones as inhibitors of SARS-CoV 3CL protease</article-title></title-group><contrib-group><contrib contrib-type="author"><name><surname>Shao</surname><given-names>Yi-Ming</given-names></name><xref rid="aff1" ref-type="aff">a</xref><xref rid="aff2" ref-type="aff">b</xref><xref rid="aff3" ref-type="aff">c</xref></contrib><contrib contrib-type="author"><name><surname>Yang</surname><given-names>Wen-Bin</given-names></name><xref rid="aff1" ref-type="aff">a</xref></contrib><contrib contrib-type="author"><name><surname>Kuo</surname><given-names>Tun-Hsun</given-names></name><xref rid="aff2" ref-type="aff">b</xref></contrib><contrib contrib-type="author"><name><surname>Tsai</surname><given-names>Keng-Chang</given-names></name><xref rid="aff1" ref-type="aff">a</xref></contrib><contrib contrib-type="author"><name><surname>Lin</surname><given-names>Chun-Hung</given-names></name><xref rid="aff1" ref-type="aff">a</xref><xref rid="aff2" ref-type="aff">b</xref><xref rid="aff3" ref-type="aff">c</xref></contrib><contrib contrib-type="author"><name><surname>Yang</surname><given-names>An-Suei</given-names></name><xref rid="aff1" ref-type="aff">a</xref></contrib><contrib contrib-type="author"><name><surname>Liang</surname><given-names>Po-Huang</given-names></name><xref rid="aff1" ref-type="aff">a</xref><xref rid="aff2" ref-type="aff">b</xref><xref rid="aff3" ref-type="aff">c</xref></contrib><contrib contrib-type="author"><name><surname>Wong</surname><given-names>Chi-Huey</given-names></name><email>chwong@gate.sinica.edu.tw</email><email>wong@scripps.edu</email><xref rid="aff1" ref-type="aff">a</xref><xref rid="aff2" ref-type="aff">b</xref><xref rid="aff3" ref-type="aff">c</xref><xref rid="aff4" ref-type="aff">d</xref><xref rid="cor1" ref-type="corresp">⁎</xref></contrib></contrib-group><aff id="aff1"><label>a</label>Genomics Research Center, Academia Sinica, No. 128, Section 2, Academia Road, Taipei 11529, Taiwan</aff><aff id="aff2"><label>b</label>Institute of Biological Chemistry, Academia Sinica, No.128, Section 2, Academia Road, Taipei 11529, Taiwan</aff><aff id="aff3"><label>c</label>Institute of Biochemical Sciences, National Taiwan University, No. 1, Section 4, Roosevelt Road, Taipei 10617, Taiwan</aff><aff id="aff4"><label>d</label>Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA</aff><author-notes><corresp id="cor1"><label>⁎</label>Corresponding author. Fax: +886 2 2789 8771. <email>chwong@gate.sinica.edu.tw</email><email>wong@scripps.edu</email></corresp></author-notes><pub-date pub-type="pmc-release"><day>15</day><month>2</month><year>2008</year></pub-date><pmc-comment> PMC Release delay is 0 months and 0 days and was based on .</pmc-comment>
<pub-date pub-type="ppub"><day>15</day><month>4</month><year>2008</year></pub-date><pub-date pub-type="epub"><day>15</day><month>2</month><year>2008</year></pub-date><volume>16</volume><issue>8</issue><fpage>4652</fpage><lpage>4660</lpage><history><date date-type="received"><day>23</day><month>11</month><year>2007</year></date><date date-type="rev-recd"><day>10</day><month>2</month><year>2008</year></date><date date-type="accepted"><day>11</day><month>2</month><year>2008</year></date></history><permissions><copyright-statement>Copyright © 2008 Published by Elsevier Ltd.</copyright-statement><copyright-year>2008</copyright-year><copyright-holder></copyright-holder><license><license-p>Since January 2020 Elsevier has created a COVID-19 resource centre with free information in English and Mandarin on the novel coronavirus COVID-19. The COVID-19 resource centre is hosted on Elsevier Connect, the company's public news and information website. Elsevier hereby grants permission to make all its COVID-19-related research that is available on the COVID-19 resource centre - including this research content - immediately available in PubMed Central and other publicly funded repositories, such as the WHO COVID database with rights for unrestricted research re-use and analyses in any form or by any means with acknowledgement of the original source. These permissions are granted for free by Elsevier for as long as the COVID-19 resource centre remains active.</license-p></license></permissions><abstract abstract-type="graphical"><title>Graphical abstract</title><fig id="d32e1332" position="anchor"><graphic xlink:href="fx1"></graphic></fig></abstract><abstract><p>A series of trifluoromethyl ketones as SARS-CoV 3CL protease inhibitors was developed. The inhibitors were synthesized in four steps from commercially available compounds. Three different amino acids were explored in the P1-position and in the P2–P4 positions varying amino acids and long alkyl chain were incorporated. All inhibitors were evaluated in an in vitro assay using purified enzyme and fluorogenic substrate peptide. One of the inhibitors showed a time-dependent inhibition, with a <italic>K</italic><sub>i</sub> value of 0.3 μM after 4 h incubation.</p></abstract><kwd-group><title>Keywords</title><kwd>SARS</kwd><kwd>Protease inhibitor</kwd><kwd>Trifluoromethyl ketone</kwd><kwd>Time-dependent inhibition</kwd></kwd-group></article-meta></front></pmc><affiliations><list><country><li>Taïwan</li><li>États-Unis</li></country><region><li>Californie</li></region></list><tree><country name="Taïwan"><noRegion><name sortKey="Shao, Yi Ming" sort="Shao, Yi Ming" uniqKey="Shao Y" first="Yi-Ming" last="Shao">Yi-Ming Shao</name></noRegion><name sortKey="Kuo, Tun Hsun" sort="Kuo, Tun Hsun" uniqKey="Kuo T" first="Tun-Hsun" last="Kuo">Tun-Hsun Kuo</name><name sortKey="Liang, Po Huang" sort="Liang, Po Huang" uniqKey="Liang P" first="Po-Huang" last="Liang">Po-Huang Liang</name><name sortKey="Liang, Po Huang" sort="Liang, Po Huang" uniqKey="Liang P" first="Po-Huang" last="Liang">Po-Huang Liang</name><name sortKey="Liang, Po Huang" sort="Liang, Po Huang" uniqKey="Liang P" first="Po-Huang" last="Liang">Po-Huang Liang</name><name sortKey="Lin, Chun Hung" sort="Lin, Chun Hung" uniqKey="Lin C" first="Chun-Hung" last="Lin">Chun-Hung Lin</name><name sortKey="Lin, Chun Hung" sort="Lin, Chun Hung" uniqKey="Lin C" first="Chun-Hung" last="Lin">Chun-Hung Lin</name><name sortKey="Lin, Chun Hung" sort="Lin, Chun Hung" uniqKey="Lin C" first="Chun-Hung" last="Lin">Chun-Hung Lin</name><name sortKey="Shao, Yi Ming" sort="Shao, Yi Ming" uniqKey="Shao Y" first="Yi-Ming" last="Shao">Yi-Ming Shao</name><name sortKey="Shao, Yi Ming" sort="Shao, Yi Ming" uniqKey="Shao Y" first="Yi-Ming" last="Shao">Yi-Ming Shao</name><name sortKey="Tsai, Keng Chang" sort="Tsai, Keng Chang" uniqKey="Tsai K" first="Keng-Chang" last="Tsai">Keng-Chang Tsai</name><name sortKey="Wong, Chi Huey" sort="Wong, Chi Huey" uniqKey="Wong C" first="Chi-Huey" last="Wong">Chi-Huey Wong</name><name sortKey="Wong, Chi Huey" sort="Wong, Chi Huey" uniqKey="Wong C" first="Chi-Huey" last="Wong">Chi-Huey Wong</name><name sortKey="Wong, Chi Huey" sort="Wong, Chi Huey" uniqKey="Wong C" first="Chi-Huey" last="Wong">Chi-Huey Wong</name><name sortKey="Yang, An Suei" sort="Yang, An Suei" uniqKey="Yang A" first="An-Suei" last="Yang">An-Suei Yang</name><name sortKey="Yang, Wen Bin" sort="Yang, Wen Bin" uniqKey="Yang W" first="Wen-Bin" last="Yang">Wen-Bin Yang</name></country><country name="États-Unis"><region name="Californie"><name sortKey="Wong, Chi Huey" sort="Wong, Chi Huey" uniqKey="Wong C" first="Chi-Huey" last="Wong">Chi-Huey Wong</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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