Spatial Configuration and Three-Dimensional Conformation Directed Design, Synthesis, Antiviral Activity, and Structure-Activity Relationships of Phenanthroindolizidine Analogues.
Identifieur interne : 000F42 ( Main/Exploration ); précédent : 000F41; suivant : 000F43Spatial Configuration and Three-Dimensional Conformation Directed Design, Synthesis, Antiviral Activity, and Structure-Activity Relationships of Phenanthroindolizidine Analogues.
Auteurs : Bo Su [République populaire de Chine] ; Chunlong Cai [République populaire de Chine] ; Meng Deng [République populaire de Chine] ; Qingmin Wang [République populaire de Chine]Source :
- Journal of agricultural and food chemistry [ 1520-5118 ] ; 2016.
Descripteurs français
- KwdFr :
- MESH :
- pharmacologie : Antiviraux, Indolizine, Phénanthrolines.
- synthèse chimique : Antiviraux.
- Antiviraux, Conception de médicament, Conformation moléculaire, Indolizine, Phénanthrolines, Relation structure-activité, Virus de la mosaïque du tabac.
English descriptors
- KwdEn :
- Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Drug Design, Indolizines (chemistry), Indolizines (pharmacology), Molecular Conformation, Phenanthrolines (chemistry), Phenanthrolines (pharmacology), Structure-Activity Relationship, Tobacco Mosaic Virus (drug effects).
- MESH :
- chemical , chemical synthesis : Antiviral Agents.
- chemical , chemistry : Antiviral Agents, Indolizines, Phenanthrolines.
- chemical , pharmacology : Antiviral Agents, Indolizines, Phenanthrolines.
- drug effects : Tobacco Mosaic Virus.
- Drug Design, Molecular Conformation, Structure-Activity Relationship.
Abstract
Our recent investigation on the antiviral activities against tobacco mosaic virus (TMV) of phenanthroindolizidine alkaloid analogues preliminarily revealed that the basic skeleton and substitution pattern at the C13a position of the molecule, which are closely related to the spatial arrangement of the molecule, have great effects on the biological activity. To further study the in-depth influence of spatial configuration and three-dimensional (3D) conformation of the molecules on their anti-TMV activities and related structure-activity relationship (SAR), a series of D-ring opened derivatives 3, 4, 5a-5j, 6, and 7, chiral 13a- and/or 14-substituted phenanthroindolizidine analogues 10-12 and 18-20, and their enantiomers ent-10-ent-12 and ent-18-ent-20 were synthesized and evaluated for their anti-TMV activities. Bioassay results showed that most of the chiral phenanthroindolizidines displayed good to excellent in vivo anti-TMV activity. Among these compounds, ent-11 showed more potent activity than Ningnanmycin (one of the most successful commercial antiviral agents), thus emerging as a potential inhibitor of the plant virus. Further SARs were also discussed for the first time under the chiral scenario, demonstrating that both spatial configuration and 3D conformation of the molecules are crucial for keeping high anti-TMV activity.
DOI: 10.1021/acs.jafc.5b06112
PubMed: 26923726
Affiliations:
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China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071</wicri:regionArea><placeName><settlement type="city">Tianjin</settlement></placeName></affiliation></author><author><name sortKey="Deng, Meng" sort="Deng, Meng" uniqKey="Deng M" first="Meng" last="Deng">Meng Deng</name><affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, People's Republic of China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory of Elemento-Organic Chemistry, Research Institute of 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300071</wicri:regionArea><placeName><settlement type="city">Tianjin</settlement></placeName></affiliation></author></analytic><series><title level="j">Journal of agricultural and food chemistry</title><idno type="eISSN">1520-5118</idno><imprint><date when="2016" type="published">2016</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>Drug Design</term><term>Indolizines (chemistry)</term><term>Indolizines (pharmacology)</term><term>Molecular Conformation</term><term>Phenanthrolines (chemistry)</term><term>Phenanthrolines (pharmacology)</term><term>Structure-Activity Relationship</term><term>Tobacco Mosaic Virus (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Antiviraux ()</term><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse 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xml:lang="fr"><term>Antiviraux</term><term>Indolizine</term><term>Phénanthrolines</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antiviraux</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Drug Design</term><term>Molecular Conformation</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Antiviraux</term><term>Conception de médicament</term><term>Conformation moléculaire</term><term>Indolizine</term><term>Phénanthrolines</term><term>Relation structure-activité</term><term>Virus de la mosaïque du tabac</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Our recent investigation on the antiviral activities against tobacco mosaic virus (TMV) of phenanthroindolizidine alkaloid analogues preliminarily revealed that the basic skeleton and substitution pattern at the C13a position of the molecule, which are closely related to the spatial arrangement of the molecule, have great effects on the biological activity. To further study the in-depth influence of spatial configuration and three-dimensional (3D) conformation of the molecules on their anti-TMV activities and related structure-activity relationship (SAR), a series of D-ring opened derivatives 3, 4, 5a-5j, 6, and 7, chiral 13a- and/or 14-substituted phenanthroindolizidine analogues 10-12 and 18-20, and their enantiomers ent-10-ent-12 and ent-18-ent-20 were synthesized and evaluated for their anti-TMV activities. Bioassay results showed that most of the chiral phenanthroindolizidines displayed good to excellent in vivo anti-TMV activity. Among these compounds, ent-11 showed more potent activity than Ningnanmycin (one of the most successful commercial antiviral agents), thus emerging as a potential inhibitor of the plant virus. Further SARs were also discussed for the first time under the chiral scenario, demonstrating that both spatial configuration and 3D conformation of the molecules are crucial for keeping high anti-TMV activity. </div></front></TEI><affiliations><list><country><li>République populaire de Chine</li></country><settlement><li>Tianjin</li></settlement></list><tree><country name="République populaire de Chine"><noRegion><name sortKey="Su, Bo" sort="Su, Bo" uniqKey="Su B" first="Bo" last="Su">Bo Su</name></noRegion><name sortKey="Cai, Chunlong" sort="Cai, Chunlong" uniqKey="Cai C" first="Chunlong" last="Cai">Chunlong Cai</name><name sortKey="Deng, Meng" sort="Deng, Meng" uniqKey="Deng M" first="Meng" last="Deng">Meng Deng</name><name sortKey="Wang, Qingmin" sort="Wang, Qingmin" uniqKey="Wang Q" first="Qingmin" last="Wang">Qingmin Wang</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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