Synthesis and evaluation of novel alpha-amino cyclic boronates as inhibitors of HCV NS3 protease.
Identifieur interne : 001694 ( PubMed/Corpus ); précédent : 001693; suivant : 001695Synthesis and evaluation of novel alpha-amino cyclic boronates as inhibitors of HCV NS3 protease.
Auteurs : Xianfeng Li ; Yong-Kang Zhang ; Yang Liu ; Charles Z. Ding ; Qun Li ; Yasheen Zhou ; Jacob J. Plattner ; Stephen J. Baker ; Xuelei Qian ; Dazhong Fan ; Liang Liao ; Zhi-Jie Ni ; Gemma V. White ; Jackie E. Mordaunt ; Linos X. Lazarides ; Martin J. Slater ; Richard L. Jarvest ; Pia Thommes ; Malcolm Ellis ; Colin M. Edge ; Julia A. Hubbard ; Don Somers ; Paul Rowland ; Pamela Nassau ; Bill Mcdowell ; Tadeusz J. Skarzynski ; Wieslaw M. Kazmierski ; Richard M. Grimes ; Lois L. Wright ; Gary K. Smith ; Wuxin Zou ; Jon Wright ; Lewis E. PennicottSource :
- Bioorganic & medicinal chemistry letters [ 1464-3405 ] ; 2010.
English descriptors
- KwdEn :
- Boronic Acids (chemical synthesis), Boronic Acids (pharmacology), Boronic Acids (therapeutic use), Catalytic Domain, Drug Design, Hepacivirus (drug effects), Hepacivirus (enzymology), Molecular Structure, Serine (chemistry), Structure-Activity Relationship, Viral Nonstructural Proteins (antagonists & inhibitors).
- MESH :
- chemical , antagonists & inhibitors : Viral Nonstructural Proteins.
- chemical , chemical synthesis : Boronic Acids.
- chemical , chemistry : Serine.
- chemical , pharmacology : Boronic Acids.
- chemical , therapeutic use : Boronic Acids.
- drug effects : Hepacivirus.
- enzymology : Hepacivirus.
- Catalytic Domain, Drug Design, Molecular Structure, Structure-Activity Relationship.
Abstract
We have designed and synthesized a novel series of alpha-amino cyclic boronates and incorporated them successfully in several acyclic templates at the P1 position. These compounds are inhibitors of the HCV NS3 serine protease, and structural studies show that they inhibit the NS3 protease by trapping the Ser-139 hydroxyl group in the active site. Synthetic methodologies and SARs of this series of compounds are described.
DOI: 10.1016/j.bmcl.2010.04.129
PubMed: 20493689
Links to Exploration step
pubmed:20493689Le document en format XML
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Hubbard</name></author><author><name sortKey="Somers, Don" sort="Somers, Don" uniqKey="Somers D" first="Don" last="Somers">Don Somers</name></author><author><name sortKey="Rowland, Paul" sort="Rowland, Paul" uniqKey="Rowland P" first="Paul" last="Rowland">Paul Rowland</name></author><author><name sortKey="Nassau, Pamela" sort="Nassau, Pamela" uniqKey="Nassau P" first="Pamela" last="Nassau">Pamela Nassau</name></author><author><name sortKey="Mcdowell, Bill" sort="Mcdowell, Bill" uniqKey="Mcdowell B" first="Bill" last="Mcdowell">Bill Mcdowell</name></author><author><name sortKey="Skarzynski, Tadeusz J" sort="Skarzynski, Tadeusz J" uniqKey="Skarzynski T" first="Tadeusz J" last="Skarzynski">Tadeusz J. Skarzynski</name></author><author><name sortKey="Kazmierski, Wieslaw M" sort="Kazmierski, Wieslaw M" uniqKey="Kazmierski W" first="Wieslaw M" last="Kazmierski">Wieslaw M. Kazmierski</name></author><author><name sortKey="Grimes, Richard M" sort="Grimes, Richard M" uniqKey="Grimes R" first="Richard M" last="Grimes">Richard M. Grimes</name></author><author><name sortKey="Wright, Lois L" sort="Wright, Lois L" uniqKey="Wright L" first="Lois L" last="Wright">Lois L. Wright</name></author><author><name sortKey="Smith, Gary K" sort="Smith, Gary K" uniqKey="Smith G" first="Gary K" last="Smith">Gary K. Smith</name></author><author><name sortKey="Zou, Wuxin" sort="Zou, Wuxin" uniqKey="Zou W" first="Wuxin" last="Zou">Wuxin Zou</name></author><author><name sortKey="Wright, Jon" sort="Wright, Jon" uniqKey="Wright J" first="Jon" last="Wright">Jon Wright</name></author><author><name sortKey="Pennicott, Lewis E" sort="Pennicott, Lewis E" uniqKey="Pennicott L" first="Lewis E" last="Pennicott">Lewis E. Pennicott</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2010">2010</date><idno type="RBID">pubmed:20493689</idno><idno type="pmid">20493689</idno><idno type="doi">10.1016/j.bmcl.2010.04.129</idno><idno type="wicri:Area/PubMed/Corpus">001694</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">001694</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Synthesis and evaluation of novel alpha-amino cyclic boronates as inhibitors of HCV NS3 protease.</title><author><name sortKey="Li, Xianfeng" sort="Li, Xianfeng" uniqKey="Li X" first="Xianfeng" last="Li">Xianfeng Li</name><affiliation><nlm:affiliation>Anacor Pharmaceuticals, Inc., Palo Alto, CA 94303, USA. xli@anacor.com</nlm:affiliation></affiliation></author><author><name sortKey="Zhang, Yong Kang" sort="Zhang, Yong Kang" uniqKey="Zhang Y" first="Yong-Kang" last="Zhang">Yong-Kang Zhang</name></author><author><name sortKey="Liu, Yang" sort="Liu, Yang" uniqKey="Liu Y" first="Yang" last="Liu">Yang Liu</name></author><author><name sortKey="Ding, Charles Z" sort="Ding, Charles Z" uniqKey="Ding C" first="Charles Z" last="Ding">Charles Z. Ding</name></author><author><name sortKey="Li, Qun" sort="Li, Qun" uniqKey="Li Q" first="Qun" last="Li">Qun Li</name></author><author><name sortKey="Zhou, Yasheen" sort="Zhou, Yasheen" uniqKey="Zhou Y" first="Yasheen" last="Zhou">Yasheen Zhou</name></author><author><name sortKey="Plattner, Jacob J" sort="Plattner, Jacob J" uniqKey="Plattner J" first="Jacob J" last="Plattner">Jacob J. Plattner</name></author><author><name sortKey="Baker, Stephen J" sort="Baker, Stephen J" uniqKey="Baker S" first="Stephen J" last="Baker">Stephen J. Baker</name></author><author><name sortKey="Qian, Xuelei" sort="Qian, Xuelei" uniqKey="Qian X" first="Xuelei" last="Qian">Xuelei Qian</name></author><author><name sortKey="Fan, Dazhong" sort="Fan, Dazhong" uniqKey="Fan D" first="Dazhong" last="Fan">Dazhong Fan</name></author><author><name sortKey="Liao, Liang" sort="Liao, Liang" uniqKey="Liao L" first="Liang" last="Liao">Liang Liao</name></author><author><name sortKey="Ni, Zhi Jie" sort="Ni, Zhi Jie" uniqKey="Ni Z" first="Zhi-Jie" last="Ni">Zhi-Jie Ni</name></author><author><name sortKey="White, Gemma V" sort="White, Gemma V" uniqKey="White G" first="Gemma V" last="White">Gemma V. White</name></author><author><name sortKey="Mordaunt, Jackie E" sort="Mordaunt, Jackie E" uniqKey="Mordaunt J" first="Jackie E" last="Mordaunt">Jackie E. Mordaunt</name></author><author><name sortKey="Lazarides, Linos X" sort="Lazarides, Linos X" uniqKey="Lazarides L" first="Linos X" last="Lazarides">Linos X. Lazarides</name></author><author><name sortKey="Slater, Martin J" sort="Slater, Martin J" uniqKey="Slater M" first="Martin J" last="Slater">Martin J. Slater</name></author><author><name sortKey="Jarvest, Richard L" sort="Jarvest, Richard L" uniqKey="Jarvest R" first="Richard L" last="Jarvest">Richard L. Jarvest</name></author><author><name sortKey="Thommes, Pia" sort="Thommes, Pia" uniqKey="Thommes P" first="Pia" last="Thommes">Pia Thommes</name></author><author><name sortKey="Ellis, Malcolm" sort="Ellis, Malcolm" uniqKey="Ellis M" first="Malcolm" last="Ellis">Malcolm Ellis</name></author><author><name sortKey="Edge, Colin M" sort="Edge, Colin M" uniqKey="Edge C" first="Colin M" last="Edge">Colin M. Edge</name></author><author><name sortKey="Hubbard, Julia A" sort="Hubbard, Julia A" uniqKey="Hubbard J" first="Julia A" last="Hubbard">Julia A. Hubbard</name></author><author><name sortKey="Somers, Don" sort="Somers, Don" uniqKey="Somers D" first="Don" last="Somers">Don Somers</name></author><author><name sortKey="Rowland, Paul" sort="Rowland, Paul" uniqKey="Rowland P" first="Paul" last="Rowland">Paul Rowland</name></author><author><name sortKey="Nassau, Pamela" sort="Nassau, Pamela" uniqKey="Nassau P" first="Pamela" last="Nassau">Pamela Nassau</name></author><author><name sortKey="Mcdowell, Bill" sort="Mcdowell, Bill" uniqKey="Mcdowell B" first="Bill" last="Mcdowell">Bill Mcdowell</name></author><author><name sortKey="Skarzynski, Tadeusz J" sort="Skarzynski, Tadeusz J" uniqKey="Skarzynski T" first="Tadeusz J" last="Skarzynski">Tadeusz J. Skarzynski</name></author><author><name sortKey="Kazmierski, Wieslaw M" sort="Kazmierski, Wieslaw M" uniqKey="Kazmierski W" first="Wieslaw M" last="Kazmierski">Wieslaw M. Kazmierski</name></author><author><name sortKey="Grimes, Richard M" sort="Grimes, Richard M" uniqKey="Grimes R" first="Richard M" last="Grimes">Richard M. Grimes</name></author><author><name sortKey="Wright, Lois L" sort="Wright, Lois L" uniqKey="Wright L" first="Lois L" last="Wright">Lois L. Wright</name></author><author><name sortKey="Smith, Gary K" sort="Smith, Gary K" uniqKey="Smith G" first="Gary K" last="Smith">Gary K. Smith</name></author><author><name sortKey="Zou, Wuxin" sort="Zou, Wuxin" uniqKey="Zou W" first="Wuxin" last="Zou">Wuxin Zou</name></author><author><name sortKey="Wright, Jon" sort="Wright, Jon" uniqKey="Wright J" first="Jon" last="Wright">Jon Wright</name></author><author><name sortKey="Pennicott, Lewis E" sort="Pennicott, Lewis E" uniqKey="Pennicott L" first="Lewis E" last="Pennicott">Lewis E. Pennicott</name></author></analytic><series><title level="j">Bioorganic & medicinal chemistry letters</title><idno type="eISSN">1464-3405</idno><imprint><date when="2010" type="published">2010</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Boronic Acids (chemical synthesis)</term><term>Boronic Acids (pharmacology)</term><term>Boronic Acids (therapeutic use)</term><term>Catalytic Domain</term><term>Drug Design</term><term>Hepacivirus (drug effects)</term><term>Hepacivirus (enzymology)</term><term>Molecular Structure</term><term>Serine (chemistry)</term><term>Structure-Activity Relationship</term><term>Viral Nonstructural Proteins (antagonists & inhibitors)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>Viral Nonstructural Proteins</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Boronic Acids</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Serine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Boronic Acids</term></keywords><keywords scheme="MESH" type="chemical" qualifier="therapeutic use" xml:lang="en"><term>Boronic Acids</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Hepacivirus</term></keywords><keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>Hepacivirus</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Catalytic Domain</term><term>Drug Design</term><term>Molecular Structure</term><term>Structure-Activity Relationship</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">We have designed and synthesized a novel series of alpha-amino cyclic boronates and incorporated them successfully in several acyclic templates at the P1 position. These compounds are inhibitors of the HCV NS3 serine protease, and structural studies show that they inhibit the NS3 protease by trapping the Ser-139 hydroxyl group in the active site. Synthetic methodologies and SARs of this series of compounds are described.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">20493689</PMID><DateCompleted><Year>2010</Year><Month>09</Month><Day>13</Day></DateCompleted><DateRevised><Year>2013</Year><Month>11</Month><Day>21</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1464-3405</ISSN><JournalIssue CitedMedium="Internet"><Volume>20</Volume><Issue>12</Issue><PubDate><Year>2010</Year><Month>Jun</Month><Day>15</Day></PubDate></JournalIssue><Title>Bioorganic & medicinal chemistry letters</Title><ISOAbbreviation>Bioorg. Med. Chem. Lett.</ISOAbbreviation></Journal><ArticleTitle>Synthesis and evaluation of novel alpha-amino cyclic boronates as inhibitors of HCV NS3 protease.</ArticleTitle><Pagination><MedlinePgn>3550-6</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.bmcl.2010.04.129</ELocationID><Abstract><AbstractText>We have designed and synthesized a novel series of alpha-amino cyclic boronates and incorporated them successfully in several acyclic templates at the P1 position. These compounds are inhibitors of the HCV NS3 serine protease, and structural studies show that they inhibit the NS3 protease by trapping the Ser-139 hydroxyl group in the active site. Synthetic methodologies and SARs of this series of compounds are described.</AbstractText><CopyrightInformation>Copyright 2010 Elsevier Ltd. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Li</LastName><ForeName>Xianfeng</ForeName><Initials>X</Initials><AffiliationInfo><Affiliation>Anacor Pharmaceuticals, Inc., Palo Alto, CA 94303, USA. xli@anacor.com</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zhang</LastName><ForeName>Yong-Kang</ForeName><Initials>YK</Initials></Author><Author ValidYN="Y"><LastName>Liu</LastName><ForeName>Yang</ForeName><Initials>Y</Initials></Author><Author ValidYN="Y"><LastName>Ding</LastName><ForeName>Charles Z</ForeName><Initials>CZ</Initials></Author><Author ValidYN="Y"><LastName>Li</LastName><ForeName>Qun</ForeName><Initials>Q</Initials></Author><Author ValidYN="Y"><LastName>Zhou</LastName><ForeName>Yasheen</ForeName><Initials>Y</Initials></Author><Author ValidYN="Y"><LastName>Plattner</LastName><ForeName>Jacob J</ForeName><Initials>JJ</Initials></Author><Author ValidYN="Y"><LastName>Baker</LastName><ForeName>Stephen J</ForeName><Initials>SJ</Initials></Author><Author ValidYN="Y"><LastName>Qian</LastName><ForeName>Xuelei</ForeName><Initials>X</Initials></Author><Author ValidYN="Y"><LastName>Fan</LastName><ForeName>Dazhong</ForeName><Initials>D</Initials></Author><Author ValidYN="Y"><LastName>Liao</LastName><ForeName>Liang</ForeName><Initials>L</Initials></Author><Author ValidYN="Y"><LastName>Ni</LastName><ForeName>Zhi-Jie</ForeName><Initials>ZJ</Initials></Author><Author ValidYN="Y"><LastName>White</LastName><ForeName>Gemma V</ForeName><Initials>GV</Initials></Author><Author ValidYN="Y"><LastName>Mordaunt</LastName><ForeName>Jackie E</ForeName><Initials>JE</Initials></Author><Author ValidYN="Y"><LastName>Lazarides</LastName><ForeName>Linos X</ForeName><Initials>LX</Initials></Author><Author ValidYN="Y"><LastName>Slater</LastName><ForeName>Martin J</ForeName><Initials>MJ</Initials></Author><Author ValidYN="Y"><LastName>Jarvest</LastName><ForeName>Richard L</ForeName><Initials>RL</Initials></Author><Author ValidYN="Y"><LastName>Thommes</LastName><ForeName>Pia</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>Ellis</LastName><ForeName>Malcolm</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Edge</LastName><ForeName>Colin M</ForeName><Initials>CM</Initials></Author><Author ValidYN="Y"><LastName>Hubbard</LastName><ForeName>Julia A</ForeName><Initials>JA</Initials></Author><Author ValidYN="Y"><LastName>Somers</LastName><ForeName>Don</ForeName><Initials>D</Initials></Author><Author ValidYN="Y"><LastName>Rowland</LastName><ForeName>Paul</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>Nassau</LastName><ForeName>Pamela</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>McDowell</LastName><ForeName>Bill</ForeName><Initials>B</Initials></Author><Author ValidYN="Y"><LastName>Skarzynski</LastName><ForeName>Tadeusz J</ForeName><Initials>TJ</Initials></Author><Author ValidYN="Y"><LastName>Kazmierski</LastName><ForeName>Wieslaw M</ForeName><Initials>WM</Initials></Author><Author ValidYN="Y"><LastName>Grimes</LastName><ForeName>Richard M</ForeName><Initials>RM</Initials></Author><Author ValidYN="Y"><LastName>Wright</LastName><ForeName>Lois L</ForeName><Initials>LL</Initials></Author><Author ValidYN="Y"><LastName>Smith</LastName><ForeName>Gary K</ForeName><Initials>GK</Initials></Author><Author ValidYN="Y"><LastName>Zou</LastName><ForeName>Wuxin</ForeName><Initials>W</Initials></Author><Author ValidYN="Y"><LastName>Wright</LastName><ForeName>Jon</ForeName><Initials>J</Initials></Author><Author ValidYN="Y"><LastName>Pennicott</LastName><ForeName>Lewis E</ForeName><Initials>LE</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2010</Year><Month>05</Month><Day>20</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Bioorg Med Chem Lett</MedlineTA><NlmUniqueID>9107377</NlmUniqueID><ISSNLinking>0960-894X</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D001897">Boronic Acids</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C084422">NS3 protein, hepatitis C virus</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D017361">Viral Nonstructural Proteins</NameOfSubstance></Chemical><Chemical><RegistryNumber>452VLY9402</RegistryNumber><NameOfSubstance UI="D012694">Serine</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D001897" MajorTopicYN="N">Boronic Acids</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName><QualifierName UI="Q000627" MajorTopicYN="N">therapeutic use</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D020134" MajorTopicYN="N">Catalytic Domain</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015195" MajorTopicYN="N">Drug Design</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D016174" MajorTopicYN="N">Hepacivirus</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName><QualifierName UI="Q000201" MajorTopicYN="N">enzymology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D012694" MajorTopicYN="N">Serine</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D017361" MajorTopicYN="N">Viral Nonstructural Proteins</DescriptorName><QualifierName UI="Q000037" MajorTopicYN="Y">antagonists & inhibitors</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2010</Year><Month>03</Month><Day>16</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2010</Year><Month>04</Month><Day>26</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2010</Year><Month>04</Month><Day>27</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2010</Year><Month>5</Month><Day>25</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2010</Year><Month>5</Month><Day>25</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2010</Year><Month>9</Month><Day>14</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">20493689</ArticleId><ArticleId IdType="pii">S0960-894X(10)00607-4</ArticleId><ArticleId IdType="doi">10.1016/j.bmcl.2010.04.129</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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