Design, synthesis, antiviral activity, and structure-activity relationships (SARs) of two types of structurally novel phenanthroindo/quinolizidine analogues.
Identifieur interne : 001664 ( Main/Exploration ); précédent : 001663; suivant : 001665Design, synthesis, antiviral activity, and structure-activity relationships (SARs) of two types of structurally novel phenanthroindo/quinolizidine analogues.
Auteurs : Bo Su [République populaire de Chine] ; Fazhong Chen ; Lizhong Wang ; Qingmin WangSource :
- Journal of agricultural and food chemistry [ 1520-5118 ] ; 2014.
Descripteurs français
- KwdFr :
- Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Conception de médicament, Indolizidines (pharmacologie), Indolizidines (synthèse chimique), Indolizine (), Maladies des plantes (virologie), Phénanthrolines (), Phénanthrènes (pharmacologie), Phénanthrènes (synthèse chimique), Quinolizines (), Relation structure-activité, Virus de la mosaïque du tabac ().
- MESH :
- pharmacologie : Antiviraux, Indolizidines, Phénanthrènes.
- synthèse chimique : Antiviraux, Indolizidines, Phénanthrènes.
- virologie : Maladies des plantes.
- Conception de médicament, Indolizine, Phénanthrolines, Quinolizines, Relation structure-activité, Virus de la mosaïque du tabac.
English descriptors
- KwdEn :
- Antiviral Agents (chemical synthesis), Antiviral Agents (pharmacology), Drug Design, Indolizidines (chemical synthesis), Indolizidines (pharmacology), Indolizines (chemistry), Phenanthrenes (chemical synthesis), Phenanthrenes (pharmacology), Phenanthrolines (chemistry), Plant Diseases (virology), Quinolizines (chemistry), Structure-Activity Relationship, Tobacco Mosaic Virus (drug effects).
- MESH :
- chemical , chemical synthesis : Antiviral Agents, Indolizidines, Phenanthrenes.
- chemical , chemistry : Indolizines, Phenanthrolines, Quinolizines.
- chemical , pharmacology : Antiviral Agents, Indolizidines, Phenanthrenes.
- drug effects : Tobacco Mosaic Virus.
- virology : Plant Diseases.
- Drug Design, Structure-Activity Relationship.
Abstract
To investigate the influence of the variation of the original skeletons of natural phenanthroindo/quinolizidine alkaloids on antiviral activities, two types of structurally totally novel analogues 7a, 7b, 16a, and 16b were designed, synthesized, and evaluated against tobacco mosaic virus (TMV) for the first time. Bioassay results indicated that all four of the newly designed analogues showed good to excellent antiviral activities, among which analogue 16a dispalyed comparable activity with that of ningnanmycin, perhaps one of the most successful commercial antiviral agents, thus emerging as a potential inhibitor of plant virus and serving as a new lead for further optimization. Further structure-activity relationships are also discussed, demonstrating for the first time that the same changes of the original skeletons of phenanthroindolizidine and phenanthroquinolizidine exihibted totally different antiviral activities results, providing some original and useful information about the preferential conformation for maintaining high activities.
DOI: 10.1021/jf405562r
PubMed: 24467600
Affiliations:
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Engineering (Tianjin), Tianjin 300071, 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, Nankai University, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071</wicri:regionArea><placeName><settlement type="city">Tianjin</settlement></placeName></affiliation></author><author><name sortKey="Chen, Fazhong" sort="Chen, Fazhong" uniqKey="Chen F" first="Fazhong" last="Chen">Fazhong Chen</name></author><author><name sortKey="Wang, Lizhong" sort="Wang, Lizhong" uniqKey="Wang L" first="Lizhong" last="Wang">Lizhong Wang</name></author><author><name sortKey="Wang, Qingmin" sort="Wang, Qingmin" uniqKey="Wang Q" first="Qingmin" last="Wang">Qingmin Wang</name></author></analytic><series><title level="j">Journal of agricultural and food chemistry</title><idno type="eISSN">1520-5118</idno><imprint><date when="2014" type="published">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral Agents (chemical synthesis)</term><term>Antiviral Agents (pharmacology)</term><term>Drug Design</term><term>Indolizidines (chemical synthesis)</term><term>Indolizidines (pharmacology)</term><term>Indolizines (chemistry)</term><term>Phenanthrenes (chemical synthesis)</term><term>Phenanthrenes (pharmacology)</term><term>Phenanthrolines (chemistry)</term><term>Plant Diseases (virology)</term><term>Quinolizines (chemistry)</term><term>Structure-Activity Relationship</term><term>Tobacco Mosaic Virus (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse chimique)</term><term>Conception de médicament</term><term>Indolizidines (pharmacologie)</term><term>Indolizidines (synthèse chimique)</term><term>Indolizine ()</term><term>Maladies des plantes (virologie)</term><term>Phénanthrolines ()</term><term>Phénanthrènes (pharmacologie)</term><term>Phénanthrènes (synthèse chimique)</term><term>Quinolizines ()</term><term>Relation structure-activité</term><term>Virus de la mosaïque du tabac ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term><term>Indolizidines</term><term>Phenanthrenes</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Indolizines</term><term>Phenanthrolines</term><term>Quinolizines</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Indolizidines</term><term>Phenanthrenes</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Tobacco Mosaic Virus</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiviraux</term><term>Indolizidines</term><term>Phénanthrènes</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antiviraux</term><term>Indolizidines</term><term>Phénanthrènes</term></keywords><keywords scheme="MESH" qualifier="virologie" xml:lang="fr"><term>Maladies des plantes</term></keywords><keywords scheme="MESH" qualifier="virology" xml:lang="en"><term>Plant Diseases</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Drug Design</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Conception de médicament</term><term>Indolizine</term><term>Phénanthrolines</term><term>Quinolizines</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">To investigate the influence of the variation of the original skeletons of natural phenanthroindo/quinolizidine alkaloids on antiviral activities, two types of structurally totally novel analogues 7a, 7b, 16a, and 16b were designed, synthesized, and evaluated against tobacco mosaic virus (TMV) for the first time. Bioassay results indicated that all four of the newly designed analogues showed good to excellent antiviral activities, among which analogue 16a dispalyed comparable activity with that of ningnanmycin, perhaps one of the most successful commercial antiviral agents, thus emerging as a potential inhibitor of plant virus and serving as a new lead for further optimization. Further structure-activity relationships are also discussed, demonstrating for the first time that the same changes of the original skeletons of phenanthroindolizidine and phenanthroquinolizidine exihibted totally different antiviral activities results, providing some original and useful information about the preferential conformation for maintaining high activities. </div></front></TEI><affiliations><list><country><li>République populaire de Chine</li></country><settlement><li>Tianjin</li></settlement></list><tree><noCountry><name sortKey="Chen, Fazhong" sort="Chen, Fazhong" uniqKey="Chen F" first="Fazhong" last="Chen">Fazhong Chen</name><name sortKey="Wang, Lizhong" sort="Wang, Lizhong" uniqKey="Wang L" first="Lizhong" last="Wang">Lizhong Wang</name><name sortKey="Wang, Qingmin" sort="Wang, Qingmin" uniqKey="Wang Q" first="Qingmin" last="Wang">Qingmin Wang</name></noCountry><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></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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