Design, synthesis, antiviral activity, and SARs of 13a-substituted phenanthroindolizidine alkaloid derivatives.
Identifieur interne : 001665 ( Main/Exploration ); précédent : 001664; suivant : 001666Design, synthesis, antiviral activity, and SARs of 13a-substituted phenanthroindolizidine alkaloid derivatives.
Auteurs : Bo Su [République populaire de Chine] ; Chunlong Cai [République populaire de Chine] ; Meng Deng [République populaire de Chine] ; Demin Liang [République populaire de Chine] ; Lizhong Wang [République populaire de Chine] ; Qingmin Wang [République populaire de Chine]Source :
- Bioorganic & medicinal chemistry letters [ 1464-3405 ] ; 2014.
Descripteurs français
- KwdFr :
- ARN viral (), Alcaloïdes (), Alcaloïdes (pharmacologie), Alcaloïdes (synthèse chimique), Antiviraux (), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Conception de médicament, Indolizine (), Indolizine (pharmacologie), Indolizine (synthèse chimique), Phénanthrolines (), Phénanthrolines (pharmacologie), Phénanthrolines (synthèse chimique), Relation dose-effet des médicaments, Relation structure-activité, Tests de sensibilité microbienne, Virus de la mosaïque du tabac ().
- MESH :
- pharmacologie : Alcaloïdes, Antiviraux, Indolizine, Phénanthrolines.
- synthèse chimique : Alcaloïdes, Antiviraux, Indolizine, Phénanthrolines.
- ARN viral, Alcaloïdes, Antiviraux, Conception de médicament, Indolizine, Phénanthrolines, Relation dose-effet des médicaments, Relation structure-activité, Tests de sensibilité microbienne, Virus de la mosaïque du tabac.
English descriptors
- KwdEn :
- Alkaloids (chemical synthesis), Alkaloids (chemistry), Alkaloids (pharmacology), Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Dose-Response Relationship, Drug, Drug Design, Indolizines (chemical synthesis), Indolizines (chemistry), Indolizines (pharmacology), Microbial Sensitivity Tests, Phenanthrolines (chemical synthesis), Phenanthrolines (chemistry), Phenanthrolines (pharmacology), RNA, Viral (drug effects), Structure-Activity Relationship, Tobacco Mosaic Virus (drug effects).
- MESH :
- chemical , chemical synthesis : Alkaloids, Antiviral Agents, Indolizines, Phenanthrolines.
- chemical , chemistry : Alkaloids, Antiviral Agents, Indolizines, Phenanthrolines.
- chemical , drug effects : RNA, Viral.
- chemical , pharmacology : Alkaloids, Antiviral Agents, Indolizines, Phenanthrolines.
- drug effects : Tobacco Mosaic Virus.
- Dose-Response Relationship, Drug, Drug Design, Microbial Sensitivity Tests, Structure-Activity Relationship.
Abstract
On the basis of our previous structure-activity relationship (SAR) and antiviral mechanism studies, a series of 13a-substituted phenanthroindolizidine alkaloid analogues (3a-16a, 3b, 4b, 6b, 7b, 10b, and 14b) were designed targeting tobacco mosaic virus (TMV) RNA, synthesized, and evaluated for their antiviral activity against TMV for the first time. The bioassay results showed that most of the synthesized compounds (such as 4a, 6a, 7a, 11a, 14a, 6b, and 14b) exhibited good to excellent antiviral activity against TMV both in vitro and in vivo. Especially, for inactivation effect and curative effect, compounds 4a, 6a, 7a, 11a, 14a, and 14b showed higher activity at both concentrations (500 μg mL(-1) and 100 μg mL(-1)) than commercial Ningnanmycin. Preliminary SARs showed that the substituted groups with hydrogen donor at 13a position were found to be favorable for keeping high antiviral activity. The present work demonstrates that 13a-substituted phenanthroindolizidines can be used as possible lead compounds for developing anti-TMV agents.
DOI: 10.1016/j.bmcl.2014.04.101
PubMed: 24835986
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="Cai, Chunlong" sort="Cai, Chunlong" uniqKey="Cai C" first="Chunlong" last="Cai">Chunlong Cai</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, 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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type="city">Tianjin</settlement></placeName></affiliation></author><author><name sortKey="Liang, Demin" sort="Liang, Demin" uniqKey="Liang D" first="Demin" last="Liang">Demin Liang</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, 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="Wang, Lizhong" sort="Wang, Lizhong" uniqKey="Wang L" first="Lizhong" last="Wang">Lizhong Wang</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, 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="Wang, Qingmin" sort="Wang, Qingmin" uniqKey="Wang Q" first="Qingmin" last="Wang">Qingmin Wang</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, China. Electronic address: wang98h@263.net.</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></analytic><series><title level="j">Bioorganic & medicinal chemistry letters</title><idno type="eISSN">1464-3405</idno><imprint><date when="2014" type="published">2014</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Alkaloids (chemical synthesis)</term><term>Alkaloids (chemistry)</term><term>Alkaloids (pharmacology)</term><term>Antiviral Agents (chemical synthesis)</term><term>Antiviral Agents (chemistry)</term><term>Antiviral Agents (pharmacology)</term><term>Dose-Response Relationship, Drug</term><term>Drug Design</term><term>Indolizines (chemical synthesis)</term><term>Indolizines (chemistry)</term><term>Indolizines (pharmacology)</term><term>Microbial Sensitivity Tests</term><term>Phenanthrolines (chemical synthesis)</term><term>Phenanthrolines (chemistry)</term><term>Phenanthrolines (pharmacology)</term><term>RNA, Viral (drug effects)</term><term>Structure-Activity Relationship</term><term>Tobacco Mosaic Virus (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>ARN viral ()</term><term>Alcaloïdes ()</term><term>Alcaloïdes (pharmacologie)</term><term>Alcaloïdes (synthèse chimique)</term><term>Antiviraux ()</term><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse chimique)</term><term>Conception de médicament</term><term>Indolizine ()</term><term>Indolizine (pharmacologie)</term><term>Indolizine (synthèse chimique)</term><term>Phénanthrolines ()</term><term>Phénanthrolines (pharmacologie)</term><term>Phénanthrolines (synthèse chimique)</term><term>Relation dose-effet des médicaments</term><term>Relation structure-activité</term><term>Tests de sensibilité microbienne</term><term>Virus de la mosaïque du tabac ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Alkaloids</term><term>Antiviral Agents</term><term>Indolizines</term><term>Phenanthrolines</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Alkaloids</term><term>Antiviral Agents</term><term>Indolizines</term><term>Phenanthrolines</term></keywords><keywords scheme="MESH" type="chemical" qualifier="drug effects" xml:lang="en"><term>RNA, Viral</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Alkaloids</term><term>Antiviral Agents</term><term>Indolizines</term><term>Phenanthrolines</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>Alcaloïdes</term><term>Antiviraux</term><term>Indolizine</term><term>Phénanthrolines</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Alcaloïdes</term><term>Antiviraux</term><term>Indolizine</term><term>Phénanthrolines</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Dose-Response Relationship, Drug</term><term>Drug Design</term><term>Microbial Sensitivity Tests</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>ARN viral</term><term>Alcaloïdes</term><term>Antiviraux</term><term>Conception de médicament</term><term>Indolizine</term><term>Phénanthrolines</term><term>Relation dose-effet des médicaments</term><term>Relation structure-activité</term><term>Tests de sensibilité microbienne</term><term>Virus de la mosaïque du tabac</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">On the basis of our previous structure-activity relationship (SAR) and antiviral mechanism studies, a series of 13a-substituted phenanthroindolizidine alkaloid analogues (3a-16a, 3b, 4b, 6b, 7b, 10b, and 14b) were designed targeting tobacco mosaic virus (TMV) RNA, synthesized, and evaluated for their antiviral activity against TMV for the first time. The bioassay results showed that most of the synthesized compounds (such as 4a, 6a, 7a, 11a, 14a, 6b, and 14b) exhibited good to excellent antiviral activity against TMV both in vitro and in vivo. Especially, for inactivation effect and curative effect, compounds 4a, 6a, 7a, 11a, 14a, and 14b showed higher activity at both concentrations (500 μg mL(-1) and 100 μg mL(-1)) than commercial Ningnanmycin. Preliminary SARs showed that the substituted groups with hydrogen donor at 13a position were found to be favorable for keeping high antiviral activity. The present work demonstrates that 13a-substituted phenanthroindolizidines can be used as possible lead compounds for developing anti-TMV agents.</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="Liang, Demin" sort="Liang, Demin" uniqKey="Liang D" first="Demin" last="Liang">Demin Liang</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></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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