Design, synthesis and antiviral activity of 2-(3-amino-4-piperazinylphenyl)chromone derivatives.
Identifieur interne : 000B10 ( Main/Exploration ); précédent : 000B09; suivant : 000B11Design, synthesis and antiviral activity of 2-(3-amino-4-piperazinylphenyl)chromone derivatives.
Auteurs : Mi Kyoung Kim [Corée du Sud] ; Hyunjun Yoon ; Dale Lynn Barnard ; Youhoon ChongSource :
- Chemical & pharmaceutical bulletin [ 1347-5223 ] ; 2013.
Descripteurs français
- KwdFr :
- MESH :
- pharmacologie : 4H-1-Benzopyran-4-ones, Antiviraux.
- synthèse chimique : 4H-1-Benzopyran-4-ones, Antiviraux.
- 4H-1-Benzopyran-4-ones, Antiviraux, Conception de médicament, Hepacivirus, Humains, Pipérazines, Relation structure-activité, Virus du SRAS.
English descriptors
- KwdEn :
- Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Chromones (chemical synthesis), Chromones (chemistry), Chromones (pharmacology), Drug Design, Hepacivirus (drug effects), Humans, Piperazine, Piperazines (chemistry), SARS Virus (drug effects), Structure-Activity Relationship.
- MESH :
- chemical , chemical synthesis : Antiviral Agents, Chromones.
- chemical , chemistry : Antiviral Agents, Chromones, Piperazines.
- chemical , pharmacology : Antiviral Agents, Chromones.
- drug effects : Hepacivirus, SARS Virus.
- Drug Design, Humans, Piperazine, Structure-Activity Relationship.
Abstract
Previously, we have confirmed that the antiviral activities of the chromone derivatives were controlled by the type as well as the position of the substituents attached to the chromone core structure. In the course of our ongoing efforts to optimize the antiviral activity of the chromone derivatives, we have been attempting to derivatize the chromone scaffold via introduction of various substituents. In this proof-of-concept study, we introduced a 3-amino-4-piperazinylphenyl functionality to the chromone scaffold and evaluated the antiviral activities of the resulting chromone derivatives. The synthesized 2-(3-amino-4-piperazinylphenyl)-chromones showed severe acute respiratory syndrome-corona virus (SARS-CoV)-specific antiviral activity. In particular, the 2-pyridinylpiperazinylphenyl substituents provided the resulting chromone derivatives with selective antiviral activity. Taken together, this result indicates the possible pharmacophoric role of the 2-pyridinylpiperazine functionality attached to the chromone scaffold, which warrants further in-depth structure-activity relationship study.
DOI: 10.1248/cpb.c12-01050
PubMed: 23546009
Affiliations:
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Le document en format XML
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sortKey="Barnard, Dale Lynn" sort="Barnard, Dale Lynn" uniqKey="Barnard D" first="Dale Lynn" last="Barnard">Dale Lynn Barnard</name></author><author><name sortKey="Chong, Youhoon" sort="Chong, Youhoon" uniqKey="Chong Y" first="Youhoon" last="Chong">Youhoon Chong</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2013">2013</date><idno type="RBID">pubmed:23546009</idno><idno type="pmid">23546009</idno><idno type="doi">10.1248/cpb.c12-01050</idno><idno type="wicri:Area/PubMed/Corpus">000656</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000656</idno><idno type="wicri:Area/PubMed/Curation">000656</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">000656</idno><idno type="wicri:Area/PubMed/Checkpoint">000650</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">000650</idno><idno type="wicri:Area/Ncbi/Merge">000323</idno><idno 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type="city">Séoul</settlement><region type="capital">Région capitale de Séoul</region></placeName></affiliation></author><author><name sortKey="Yoon, Hyunjun" sort="Yoon, Hyunjun" uniqKey="Yoon H" first="Hyunjun" last="Yoon">Hyunjun Yoon</name></author><author><name sortKey="Barnard, Dale Lynn" sort="Barnard, Dale Lynn" uniqKey="Barnard D" first="Dale Lynn" last="Barnard">Dale Lynn Barnard</name></author><author><name sortKey="Chong, Youhoon" sort="Chong, Youhoon" uniqKey="Chong Y" first="Youhoon" last="Chong">Youhoon Chong</name></author></analytic><series><title level="j">Chemical & pharmaceutical bulletin</title><idno type="eISSN">1347-5223</idno><imprint><date when="2013" type="published">2013</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral Agents (chemical synthesis)</term><term>Antiviral Agents (chemistry)</term><term>Antiviral Agents (pharmacology)</term><term>Chromones (chemical synthesis)</term><term>Chromones (chemistry)</term><term>Chromones (pharmacology)</term><term>Drug Design</term><term>Hepacivirus (drug effects)</term><term>Humans</term><term>Piperazine</term><term>Piperazines (chemistry)</term><term>SARS Virus (drug effects)</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>4H-1-Benzopyran-4-ones ()</term><term>4H-1-Benzopyran-4-ones (pharmacologie)</term><term>4H-1-Benzopyran-4-ones (synthèse chimique)</term><term>Antiviraux ()</term><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse chimique)</term><term>Conception de médicament</term><term>Hepacivirus ()</term><term>Humains</term><term>Pipérazines ()</term><term>Relation structure-activité</term><term>Virus du SRAS ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term><term>Chromones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Chromones</term><term>Piperazines</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Chromones</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Hepacivirus</term><term>SARS Virus</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>4H-1-Benzopyran-4-ones</term><term>Antiviraux</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>4H-1-Benzopyran-4-ones</term><term>Antiviraux</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Drug Design</term><term>Humans</term><term>Piperazine</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>4H-1-Benzopyran-4-ones</term><term>Antiviraux</term><term>Conception de médicament</term><term>Hepacivirus</term><term>Humains</term><term>Pipérazines</term><term>Relation structure-activité</term><term>Virus du SRAS</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Previously, we have confirmed that the antiviral activities of the chromone derivatives were controlled by the type as well as the position of the substituents attached to the chromone core structure. In the course of our ongoing efforts to optimize the antiviral activity of the chromone derivatives, we have been attempting to derivatize the chromone scaffold via introduction of various substituents. In this proof-of-concept study, we introduced a 3-amino-4-piperazinylphenyl functionality to the chromone scaffold and evaluated the antiviral activities of the resulting chromone derivatives. The synthesized 2-(3-amino-4-piperazinylphenyl)-chromones showed severe acute respiratory syndrome-corona virus (SARS-CoV)-specific antiviral activity. In particular, the 2-pyridinylpiperazinylphenyl substituents provided the resulting chromone derivatives with selective antiviral activity. Taken together, this result indicates the possible pharmacophoric role of the 2-pyridinylpiperazine functionality attached to the chromone scaffold, which warrants further in-depth structure-activity relationship study.</div></front></TEI><affiliations><list><country><li>Corée du Sud</li></country><region><li>Région capitale de Séoul</li></region><settlement><li>Séoul</li></settlement></list><tree><noCountry><name sortKey="Barnard, Dale Lynn" sort="Barnard, Dale Lynn" uniqKey="Barnard D" first="Dale Lynn" last="Barnard">Dale Lynn Barnard</name><name sortKey="Chong, Youhoon" sort="Chong, Youhoon" uniqKey="Chong Y" first="Youhoon" last="Chong">Youhoon Chong</name><name sortKey="Yoon, Hyunjun" sort="Yoon, Hyunjun" uniqKey="Yoon H" first="Hyunjun" last="Yoon">Hyunjun Yoon</name></noCountry><country name="Corée du Sud"><region name="Région capitale de Séoul"><name sortKey="Kim, Mi Kyoung" sort="Kim, Mi Kyoung" uniqKey="Kim M" first="Mi Kyoung" last="Kim">Mi Kyoung Kim</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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