Chemical synthesis, crystal structure, versatile evaluation of their biological activities and molecular simulations of novel pyrithiobac derivatives.
Identifieur interne : 000B70 ( Main/Exploration ); précédent : 000B69; suivant : 000B71Chemical synthesis, crystal structure, versatile evaluation of their biological activities and molecular simulations of novel pyrithiobac derivatives.
Auteurs : Ren-Jun Wu [République populaire de Chine] ; Kai-Xuan Zhou [République populaire de Chine] ; Haijin Yang [République populaire de Chine] ; Guo-Qing Song [République populaire de Chine] ; Yong-Hong Li [République populaire de Chine] ; Jia-Xin Fu [République populaire de Chine] ; Xiao Zhang [République populaire de Chine] ; Shu-Jing Yu [République populaire de Chine] ; Li-Zhong Wang [République populaire de Chine] ; Li-Xia Xiong [République populaire de Chine] ; Cong-Wei Niu [République populaire de Chine] ; Fu-Hang Song [République populaire de Chine] ; Haitao Yang [République populaire de Chine] ; Jian-Guo Wang [République populaire de Chine]Source :
- European journal of medicinal chemistry [ 1768-3254 ] ; 2019.
Descripteurs français
- KwdFr :
- Acetolactate synthase (antagonistes et inhibiteurs), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Benzoates (), Benzoates (pharmacologie), Benzoates (synthèse chimique), Champignons (), Conception de médicament, Herbicides (pharmacologie), Herbicides (synthèse chimique), Herbicides (usage thérapeutique), Modèles moléculaires, Structure moléculaire, Virus du SRAS ().
- MESH :
- antagonistes et inhibiteurs : Acetolactate synthase.
- pharmacologie : Antiviraux, Benzoates, Herbicides.
- synthèse chimique : Antiviraux, Benzoates, Herbicides.
- usage thérapeutique : Herbicides.
- Benzoates, Champignons, Conception de médicament, Modèles moléculaires, Structure moléculaire, Virus du SRAS.
English descriptors
- KwdEn :
- Acetolactate Synthase (antagonists & inhibitors), Antiviral Agents (chemical synthesis), Antiviral Agents (pharmacology), Benzoates (chemical synthesis), Benzoates (chemistry), Benzoates (pharmacology), Drug Design, Fungi (drug effects), Herbicides (chemical synthesis), Herbicides (pharmacology), Herbicides (therapeutic use), Models, Molecular, Molecular Structure, SARS Virus (drug effects).
- MESH :
- chemical , antagonists & inhibitors : Acetolactate Synthase.
- chemical , chemical synthesis : Antiviral Agents, Benzoates, Herbicides.
- chemical , chemistry : Benzoates.
- chemical , pharmacology : Antiviral Agents, Benzoates, Herbicides.
- drug effects : Fungi, SARS Virus.
- chemical , therapeutic use : Herbicides.
- Drug Design, Models, Molecular, Molecular Structure.
Abstract
Since pyrithiobac (PTB) is a successful commercial herbicide with very low toxicity against mammals, it is worth exploring its derivatives for an extensive study. Herein, a total of 35 novel compounds were chemically synthesized and single crystal of 6-6 was obtained to confirm the molecular structure of this family of compounds. The novel PTB derivatives were fully evaluated against various biological platforms. From the bioassay results, the best AHAS inhibitor 6-22 displayed weaker herbicidal activity but stronger anti-Candida activity than PTB did. For plant pathogenic fungi, 6-26 showed excellent activity at 50 mg/L dosage. Preliminary insecticidal activity and antiviral activity were also observed for some title compounds. Strikingly, 6-5 exhibited a promising inhibitory activity against SARS-CoV Mpro with IC50 of 4.471 μM and a low cellular cytotoxicity against mammalian 293 T cells. Based on the results of molecular modeling, HOMO-1 was considered to be a factor that affects AHAS inhibition and a possible binding mode of 6-5 with SARS-CoV Mpro was predicted. This is the first time that PTB derivatives have been studied as biological agents other than herbicides. The present research hence has suggested that more attentions should be paid to compounds belonging to this family to develop novel agrochemicals or medicines.
DOI: 10.1016/j.ejmech.2019.02.002
PubMed: 30784880
Affiliations:
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xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071</wicri:regionArea><wicri:noRegion>300071</wicri:noRegion></affiliation></author><author><name sortKey="Zhou, Kai Xuan" sort="Zhou, Kai Xuan" uniqKey="Zhou K" first="Kai-Xuan" last="Zhou">Kai-Xuan Zhou</name><affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Medicinal Chemical Biology, Nankai University, Tianjin, 300071, China; Tianjin International Joint Academy of Biotechnology and Medicine, Tianjin, 300457, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory of Medicinal Chemical Biology, Nankai University, Tianjin, 300071, China; Tianjin International Joint Academy of Biotechnology and Medicine, Tianjin, 300457</wicri:regionArea><wicri:noRegion>300457</wicri:noRegion></affiliation></author><author><name sortKey="Yang, Haijin" sort="Yang, Haijin" uniqKey="Yang H" first="Haijin" last="Yang">Haijin Yang</name><affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Microbial Resources, CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, China; School of Ocean Sciences, China University of Geosciences, Beijing, 100083, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory of Microbial Resources, CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, China; School of Ocean Sciences, China University of Geosciences, Beijing, 100083</wicri:regionArea><wicri:noRegion>100083</wicri:noRegion></affiliation></author><author><name sortKey="Song, Guo Qing" sort="Song, Guo Qing" uniqKey="Song G" first="Guo-Qing" last="Song">Guo-Qing Song</name><affiliation wicri:level="1"><nlm:affiliation>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071</wicri:regionArea><wicri:noRegion>300071</wicri:noRegion></affiliation></author><author><name sortKey="Li, Yong Hong" sort="Li, Yong Hong" uniqKey="Li Y" first="Yong-Hong" last="Li">Yong-Hong Li</name><affiliation wicri:level="1"><nlm:affiliation>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071</wicri:regionArea><wicri:noRegion>300071</wicri:noRegion></affiliation></author><author><name sortKey="Fu, Jia Xin" sort="Fu, Jia Xin" uniqKey="Fu J" first="Jia-Xin" last="Fu">Jia-Xin Fu</name><affiliation wicri:level="1"><nlm:affiliation>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071</wicri:regionArea><wicri:noRegion>300071</wicri:noRegion></affiliation></author><author><name sortKey="Zhang, Xiao" sort="Zhang, Xiao" uniqKey="Zhang X" first="Xiao" last="Zhang">Xiao Zhang</name><affiliation wicri:level="1"><nlm:affiliation>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071</wicri:regionArea><wicri:noRegion>300071</wicri:noRegion></affiliation></author><author><name sortKey="Yu, Shu Jing" sort="Yu, Shu Jing" uniqKey="Yu S" first="Shu-Jing" last="Yu">Shu-Jing Yu</name><affiliation wicri:level="1"><nlm:affiliation>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071</wicri:regionArea><wicri:noRegion>300071</wicri:noRegion></affiliation></author><author><name sortKey="Wang, Li Zhong" sort="Wang, Li Zhong" uniqKey="Wang L" first="Li-Zhong" last="Wang">Li-Zhong Wang</name><affiliation wicri:level="1"><nlm:affiliation>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071</wicri:regionArea><wicri:noRegion>300071</wicri:noRegion></affiliation></author><author><name sortKey="Xiong, Li Xia" sort="Xiong, Li Xia" uniqKey="Xiong L" first="Li-Xia" last="Xiong">Li-Xia Xiong</name><affiliation wicri:level="1"><nlm:affiliation>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071</wicri:regionArea><wicri:noRegion>300071</wicri:noRegion></affiliation></author><author><name sortKey="Niu, Cong Wei" sort="Niu, Cong Wei" uniqKey="Niu C" first="Cong-Wei" last="Niu">Cong-Wei Niu</name><affiliation wicri:level="1"><nlm:affiliation>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071</wicri:regionArea><wicri:noRegion>300071</wicri:noRegion></affiliation></author><author><name sortKey="Song, Fu Hang" sort="Song, Fu Hang" uniqKey="Song F" first="Fu-Hang" last="Song">Fu-Hang Song</name><affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Microbial Resources, CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101, China. Electronic address: songfuhang@163.com.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory of Microbial Resources, CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing, 100101</wicri:regionArea><wicri:noRegion>100101</wicri:noRegion></affiliation></author><author><name sortKey="Yang, Haitao" sort="Yang, Haitao" uniqKey="Yang H" first="Haitao" last="Yang">Haitao Yang</name><affiliation wicri:level="1"><nlm:affiliation>Tianjin International Joint Academy of Biotechnology and Medicine, Tianjin, 300457, China. Electronic address: yanght@tju.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Tianjin International Joint Academy of Biotechnology and Medicine, Tianjin, 300457</wicri:regionArea><wicri:noRegion>300457</wicri:noRegion></affiliation></author><author><name sortKey="Wang, Jian Guo" sort="Wang, Jian Guo" uniqKey="Wang J" first="Jian-Guo" last="Wang">Jian-Guo Wang</name><affiliation wicri:level="1"><nlm:affiliation>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071, China. Electronic address: nkwjg@nankai.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center (Tianjin), College of Chemistry, Nankai University, Tianjin, 300071</wicri:regionArea><wicri:noRegion>300071</wicri:noRegion></affiliation></author></analytic><series><title level="j">European journal of medicinal chemistry</title><idno type="eISSN">1768-3254</idno><imprint><date when="2019" type="published">2019</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Acetolactate Synthase (antagonists & inhibitors)</term><term>Antiviral Agents (chemical synthesis)</term><term>Antiviral Agents (pharmacology)</term><term>Benzoates (chemical synthesis)</term><term>Benzoates (chemistry)</term><term>Benzoates (pharmacology)</term><term>Drug Design</term><term>Fungi (drug effects)</term><term>Herbicides (chemical synthesis)</term><term>Herbicides (pharmacology)</term><term>Herbicides (therapeutic use)</term><term>Models, Molecular</term><term>Molecular Structure</term><term>SARS Virus (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Acetolactate synthase (antagonistes et inhibiteurs)</term><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse chimique)</term><term>Benzoates ()</term><term>Benzoates (pharmacologie)</term><term>Benzoates (synthèse chimique)</term><term>Champignons ()</term><term>Conception de médicament</term><term>Herbicides (pharmacologie)</term><term>Herbicides (synthèse chimique)</term><term>Herbicides (usage thérapeutique)</term><term>Modèles moléculaires</term><term>Structure moléculaire</term><term>Virus du SRAS ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>Acetolactate Synthase</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term><term>Benzoates</term><term>Herbicides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Benzoates</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Benzoates</term><term>Herbicides</term></keywords><keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Acetolactate synthase</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Fungi</term><term>SARS Virus</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiviraux</term><term>Benzoates</term><term>Herbicides</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antiviraux</term><term>Benzoates</term><term>Herbicides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="therapeutic use" xml:lang="en"><term>Herbicides</term></keywords><keywords scheme="MESH" qualifier="usage thérapeutique" xml:lang="fr"><term>Herbicides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Drug Design</term><term>Models, Molecular</term><term>Molecular Structure</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Benzoates</term><term>Champignons</term><term>Conception de médicament</term><term>Modèles moléculaires</term><term>Structure moléculaire</term><term>Virus du SRAS</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Since pyrithiobac (PTB) is a successful commercial herbicide with very low toxicity against mammals, it is worth exploring its derivatives for an extensive study. Herein, a total of 35 novel compounds were chemically synthesized and single crystal of 6-6 was obtained to confirm the molecular structure of this family of compounds. The novel PTB derivatives were fully evaluated against various biological platforms. From the bioassay results, the best AHAS inhibitor 6-22 displayed weaker herbicidal activity but stronger anti-Candida activity than PTB did. For plant pathogenic fungi, 6-26 showed excellent activity at 50 mg/L dosage. Preliminary insecticidal activity and antiviral activity were also observed for some title compounds. Strikingly, 6-5 exhibited a promising inhibitory activity against SARS-CoV M<sup>pro</sup> with IC<sub>50</sub> of 4.471 μM and a low cellular cytotoxicity against mammalian 293 T cells. Based on the results of molecular modeling, HOMO-1 was considered to be a factor that affects AHAS inhibition and a possible binding mode of 6-5 with SARS-CoV M<sup>pro</sup> was predicted. This is the first time that PTB derivatives have been studied as biological agents other than herbicides. The present research hence has suggested that more attentions should be paid to compounds belonging to this family to develop novel agrochemicals or medicines.</div></front></TEI><affiliations><list><country><li>République populaire de Chine</li></country></list><tree><country name="République populaire de Chine"><noRegion><name sortKey="Wu, Ren Jun" sort="Wu, Ren Jun" uniqKey="Wu R" first="Ren-Jun" last="Wu">Ren-Jun Wu</name></noRegion><name sortKey="Fu, Jia Xin" sort="Fu, Jia Xin" uniqKey="Fu J" first="Jia-Xin" last="Fu">Jia-Xin Fu</name><name sortKey="Li, Yong Hong" sort="Li, Yong Hong" uniqKey="Li Y" first="Yong-Hong" last="Li">Yong-Hong Li</name><name sortKey="Niu, Cong Wei" sort="Niu, Cong Wei" uniqKey="Niu C" first="Cong-Wei" last="Niu">Cong-Wei Niu</name><name sortKey="Song, Fu Hang" sort="Song, Fu Hang" uniqKey="Song F" first="Fu-Hang" last="Song">Fu-Hang Song</name><name sortKey="Song, Guo Qing" sort="Song, Guo Qing" uniqKey="Song G" first="Guo-Qing" last="Song">Guo-Qing Song</name><name sortKey="Wang, Jian Guo" sort="Wang, Jian Guo" uniqKey="Wang J" first="Jian-Guo" last="Wang">Jian-Guo Wang</name><name sortKey="Wang, Li Zhong" sort="Wang, Li Zhong" uniqKey="Wang L" first="Li-Zhong" last="Wang">Li-Zhong Wang</name><name sortKey="Xiong, Li Xia" sort="Xiong, Li Xia" uniqKey="Xiong L" first="Li-Xia" last="Xiong">Li-Xia Xiong</name><name sortKey="Yang, Haijin" sort="Yang, Haijin" uniqKey="Yang H" first="Haijin" last="Yang">Haijin Yang</name><name sortKey="Yang, Haitao" sort="Yang, Haitao" uniqKey="Yang H" first="Haitao" last="Yang">Haitao Yang</name><name sortKey="Yu, Shu Jing" sort="Yu, Shu Jing" uniqKey="Yu S" first="Shu-Jing" last="Yu">Shu-Jing Yu</name><name sortKey="Zhang, Xiao" sort="Zhang, Xiao" uniqKey="Zhang X" first="Xiao" last="Zhang">Xiao Zhang</name><name sortKey="Zhou, Kai Xuan" sort="Zhou, Kai Xuan" uniqKey="Zhou K" first="Kai-Xuan" last="Zhou">Kai-Xuan Zhou</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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