Novel α,β-unsaturated amide derivatives bearing α-amino phosphonate moiety as potential antiviral agents.
Identifieur interne : 000D98 ( Main/Exploration ); précédent : 000D97; suivant : 000D99Novel α,β-unsaturated amide derivatives bearing α-amino phosphonate moiety as potential antiviral agents.
Auteurs : Xianmin Lan [République populaire de Chine] ; Dandan Xie [République populaire de Chine] ; Limin Yin [République populaire de Chine] ; Zhenzhen Wang [République populaire de Chine] ; Jin Chen [République populaire de Chine] ; Awei Zhang [République populaire de Chine] ; Baoan Song [République populaire de Chine] ; Deyu Hu [République populaire de Chine]Source :
- Bioorganic & medicinal chemistry letters [ 1464-3405 ] ; 2017.
Descripteurs français
- KwdFr :
- Amides (), Amides (pharmacologie), Amides (synthèse chimique), Antiviraux (), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Cucumovirus (), Phosphonates (), Phosphonates (pharmacologie), Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire, Tests de sensibilité microbienne, Virus de la mosaïque du tabac ().
- MESH :
- pharmacologie : Amides, Antiviraux, Phosphonates.
- synthèse chimique : Amides, Antiviraux.
- Amides, Antiviraux, Cucumovirus, Phosphonates, Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire, Tests de sensibilité microbienne, Virus de la mosaïque du tabac.
English descriptors
- KwdEn :
- Amides (chemical synthesis), Amides (chemistry), Amides (pharmacology), Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Cucumovirus (drug effects), Dose-Response Relationship, Drug, Microbial Sensitivity Tests, Molecular Structure, Organophosphonates (chemistry), Organophosphonates (pharmacology), Structure-Activity Relationship, Tobacco Mosaic Virus (drug effects).
- MESH :
- chemical , chemical synthesis : Amides, Antiviral Agents.
- chemical , chemistry : Amides, Antiviral Agents, Organophosphonates.
- chemical , pharmacology : Amides, Antiviral Agents, Organophosphonates.
- drug effects : Cucumovirus, Tobacco Mosaic Virus.
- Dose-Response Relationship, Drug, Microbial Sensitivity Tests, Molecular Structure, Structure-Activity Relationship.
Abstract
Based on flexible construction and broad bioactivity of ferulic acid, a series of novel α,β-unsaturated amide derivatives bearing α-aminophosphonate moiety were designed, synthesized and systematically evaluated for their antiviral activity. Bioassay results indicated that some compounds exhibited good antiviral activities against cucumber mosaic virus (CMV) and tobacco mosaic virus (TMV) in vivo. Especially, compound g18 showed excellent curative and protective activities against CMV, with half-maximal effective concentration (EC50) values of 284.67μg/mL and 216.30μg/mL, which were obviously superior to that of Ningnanmycin (352.08μg/mL and 262.53μg/mL). Preliminary structure-activity relationships (SARs) analysis revealed that the introduction of electron-withdrawing group at the 2-position or 4-position of the aromatic ring is favorable for antiviral activity. Present work provides a promising template for development of potential inhibitor of plant virus.
DOI: 10.1016/j.bmcl.2017.08.048
PubMed: 28866271
Affiliations:
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District, Guiyang 550025, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025</wicri:regionArea><wicri:noRegion>Guiyang 550025</wicri:noRegion></affiliation></author><author><name sortKey="Xie, Dandan" sort="Xie, Dandan" uniqKey="Xie D" first="Dandan" last="Xie">Dandan Xie</name><affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory Breeding Base of Green Pesticide and 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550025</wicri:regionArea><wicri:noRegion>Guiyang 550025</wicri:noRegion></affiliation></author><author><name sortKey="Wang, Zhenzhen" sort="Wang, Zhenzhen" uniqKey="Wang Z" first="Zhenzhen" last="Wang">Zhenzhen Wang</name><affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025</wicri:regionArea><wicri:noRegion>Guiyang 550025</wicri:noRegion></affiliation></author><author><name sortKey="Chen, Jin" sort="Chen, Jin" uniqKey="Chen J" first="Jin" last="Chen">Jin Chen</name><affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025</wicri:regionArea><wicri:noRegion>Guiyang 550025</wicri:noRegion></affiliation></author><author><name sortKey="Zhang, Awei" sort="Zhang, Awei" uniqKey="Zhang A" first="Awei" last="Zhang">Awei Zhang</name><affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025</wicri:regionArea><wicri:noRegion>Guiyang 550025</wicri:noRegion></affiliation></author><author><name sortKey="Song, Baoan" sort="Song, Baoan" uniqKey="Song B" first="Baoan" last="Song">Baoan Song</name><affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025</wicri:regionArea><wicri:noRegion>Guiyang 550025</wicri:noRegion></affiliation></author><author><name sortKey="Hu, Deyu" sort="Hu, Deyu" uniqKey="Hu D" first="Deyu" last="Hu">Deyu Hu</name><affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China. Electronic address: dyhu@gzu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025</wicri:regionArea><wicri:noRegion>Guiyang 550025</wicri:noRegion></affiliation></author></analytic><series><title level="j">Bioorganic & medicinal chemistry letters</title><idno type="eISSN">1464-3405</idno><imprint><date when="2017" type="published">2017</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amides (chemical synthesis)</term><term>Amides (chemistry)</term><term>Amides (pharmacology)</term><term>Antiviral Agents (chemical synthesis)</term><term>Antiviral Agents (chemistry)</term><term>Antiviral Agents (pharmacology)</term><term>Cucumovirus (drug effects)</term><term>Dose-Response Relationship, Drug</term><term>Microbial Sensitivity Tests</term><term>Molecular Structure</term><term>Organophosphonates (chemistry)</term><term>Organophosphonates (pharmacology)</term><term>Structure-Activity Relationship</term><term>Tobacco Mosaic Virus (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Amides ()</term><term>Amides (pharmacologie)</term><term>Amides (synthèse chimique)</term><term>Antiviraux ()</term><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse chimique)</term><term>Cucumovirus ()</term><term>Phosphonates ()</term><term>Phosphonates (pharmacologie)</term><term>Relation dose-effet des médicaments</term><term>Relation structure-activité</term><term>Structure moléculaire</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>Amides</term><term>Antiviral Agents</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Amides</term><term>Antiviral Agents</term><term>Organophosphonates</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Amides</term><term>Antiviral Agents</term><term>Organophosphonates</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Cucumovirus</term><term>Tobacco Mosaic Virus</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Amides</term><term>Antiviraux</term><term>Phosphonates</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Amides</term><term>Antiviraux</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Dose-Response Relationship, Drug</term><term>Microbial Sensitivity Tests</term><term>Molecular Structure</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Amides</term><term>Antiviraux</term><term>Cucumovirus</term><term>Phosphonates</term><term>Relation dose-effet des médicaments</term><term>Relation structure-activité</term><term>Structure moléculaire</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">Based on flexible construction and broad bioactivity of ferulic acid, a series of novel α,β-unsaturated amide derivatives bearing α-aminophosphonate moiety were designed, synthesized and systematically evaluated for their antiviral activity. Bioassay results indicated that some compounds exhibited good antiviral activities against cucumber mosaic virus (CMV) and tobacco mosaic virus (TMV) in vivo. Especially, compound g18 showed excellent curative and protective activities against CMV, with half-maximal effective concentration (EC<sub>50</sub>) values of 284.67μg/mL and 216.30μg/mL, which were obviously superior to that of Ningnanmycin (352.08μg/mL and 262.53μg/mL). Preliminary structure-activity relationships (SARs) analysis revealed that the introduction of electron-withdrawing group at the 2-position or 4-position of the aromatic ring is favorable for antiviral activity. Present work provides a promising template for development of potential inhibitor of plant virus.</div></front></TEI><affiliations><list><country><li>République populaire de Chine</li></country></list><tree><country name="République populaire de Chine"><noRegion><name sortKey="Lan, Xianmin" sort="Lan, Xianmin" uniqKey="Lan X" first="Xianmin" last="Lan">Xianmin Lan</name></noRegion><name sortKey="Chen, Jin" sort="Chen, Jin" uniqKey="Chen J" first="Jin" last="Chen">Jin Chen</name><name sortKey="Hu, Deyu" sort="Hu, Deyu" uniqKey="Hu D" first="Deyu" last="Hu">Deyu Hu</name><name sortKey="Song, Baoan" sort="Song, Baoan" uniqKey="Song B" first="Baoan" last="Song">Baoan Song</name><name sortKey="Wang, Zhenzhen" sort="Wang, Zhenzhen" uniqKey="Wang Z" first="Zhenzhen" last="Wang">Zhenzhen Wang</name><name sortKey="Xie, Dandan" sort="Xie, Dandan" uniqKey="Xie D" first="Dandan" last="Xie">Dandan Xie</name><name sortKey="Yin, Limin" sort="Yin, Limin" uniqKey="Yin L" first="Limin" last="Yin">Limin Yin</name><name sortKey="Zhang, Awei" sort="Zhang, Awei" uniqKey="Zhang A" first="Awei" last="Zhang">Awei Zhang</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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