Design, synthesis and antifungal activity of threoninamide carbamate derivatives via pharmacophore model.
Identifieur interne : 000252 ( Main/Exploration ); précédent : 000251; suivant : 000253Design, synthesis and antifungal activity of threoninamide carbamate derivatives via pharmacophore model.
Auteurs : Xiu-Jiang Du [République populaire de Chine] ; Xing-Jie Peng [République populaire de Chine] ; Rui-Qi Zhao [République populaire de Chine] ; Wei-Guang Zhao [République populaire de Chine] ; Wei-Li Dong [République populaire de Chine] ; Xing-Hai Liu [République populaire de Chine]Source :
- Journal of enzyme inhibition and medicinal chemistry [ 1475-6374 ] ; 2020.
Descripteurs français
- KwdFr :
- Amides (composition chimique), Amides (pharmacologie), Amides (synthèse chimique), Antifongiques (composition chimique), Antifongiques (pharmacologie), Antifongiques (synthèse chimique), Champignons (effets des médicaments et des substances chimiques), Conception de médicament (MeSH), Relation dose-effet des médicaments (MeSH), Relation structure-activité (MeSH), Structure moléculaire (MeSH), Tests de sensibilité microbienne (MeSH), Thréonine (composition chimique), Thréonine (pharmacologie), Thréonine (synthèse chimique).
- MESH :
- composition chimique : Amides, Antifongiques, Thréonine.
- effets des médicaments et des substances chimiques : Champignons.
- pharmacologie : Amides, Antifongiques, Thréonine.
- synthèse chimique : Amides, Antifongiques, Thréonine.
- Conception de médicament, Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire, Tests de sensibilité microbienne.
English descriptors
- KwdEn :
- Amides (chemical synthesis), Amides (chemistry), Amides (pharmacology), Antifungal Agents (chemical synthesis), Antifungal Agents (chemistry), Antifungal Agents (pharmacology), Dose-Response Relationship, Drug (MeSH), Drug Design (MeSH), Fungi (drug effects), Microbial Sensitivity Tests (MeSH), Molecular Structure (MeSH), Structure-Activity Relationship (MeSH), Threonine (chemical synthesis), Threonine (chemistry), Threonine (pharmacology).
- MESH :
- chemical , chemical synthesis : Amides, Antifungal Agents, Threonine.
- chemical , chemistry : Amides, Antifungal Agents, Threonine.
- chemical , pharmacology : Amides, Antifungal Agents, Threonine.
- drug effects : Fungi.
- Dose-Response Relationship, Drug, Drug Design, Microbial Sensitivity Tests, Molecular Structure, Structure-Activity Relationship.
Abstract
Thirty-six novel threoninamide carbamate derivatives were designed and synthesised using active fragment-based pharmacophore model. Antifungal activities of these compounds were tested against Oomycete fungi Phytophthora capsici in vitro and in vivo. Interestingly, compound I-1, I-2, I-3, I-6 and I-7 exhibited moderate control effect (>50%) against Pseudoperonospora cubensis in greenhouse at 6.25 μg/mL, which is better than that of control. Meanwhile most of these compounds exhibited significant inhibitory against P. capsici. The other nine fungi were also tested. More importantly, some compounds exhibited remarkably high activities against Sclerotinia sclerotiorum, P. piricola and R. solan in vitro with EC50 values of 3.74-9.76 μg/mL. It is possible that the model is reliabile and this method can be used to discover lead compounds for the development of fungicides.
DOI: 10.1080/14756366.2020.1729144
PubMed: 32148108
PubMed Central: PMC7144198
Affiliations:
Links toward previous steps (curation, corpus...)
Le document en format XML
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type="city">Tianjin</settlement></placeName></affiliation></author><author><name sortKey="Peng, Xing Jie" sort="Peng, Xing Jie" uniqKey="Peng X" first="Xing-Jie" last="Peng">Xing-Jie Peng</name><affiliation wicri:level="3"><nlm:affiliation>State Key Laboratory of Elemental Organic Chemistry, Nankai University, Tianjin, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory of Elemental Organic Chemistry, Nankai University, Tianjin</wicri:regionArea><placeName><settlement type="city">Tianjin</settlement></placeName></affiliation></author><author><name sortKey="Zhao, Rui Qi" sort="Zhao, Rui Qi" uniqKey="Zhao R" first="Rui-Qi" last="Zhao">Rui-Qi Zhao</name><affiliation wicri:level="3"><nlm:affiliation>State Key Laboratory of Elemental Organic Chemistry, Nankai University, Tianjin, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory of Elemental Organic Chemistry, Nankai University, Tianjin</wicri:regionArea><placeName><settlement type="city">Tianjin</settlement></placeName></affiliation></author><author><name sortKey="Zhao, Wei Guang" sort="Zhao, Wei Guang" uniqKey="Zhao W" first="Wei-Guang" last="Zhao">Wei-Guang Zhao</name><affiliation wicri:level="3"><nlm:affiliation>State Key Laboratory of Elemental Organic Chemistry, Nankai University, Tianjin, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory of Elemental Organic Chemistry, Nankai University, Tianjin</wicri:regionArea><placeName><settlement type="city">Tianjin</settlement></placeName></affiliation></author><author><name sortKey="Dong, Wei Li" sort="Dong, Wei Li" uniqKey="Dong W" first="Wei-Li" last="Dong">Wei-Li Dong</name><affiliation wicri:level="3"><nlm:affiliation>Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics (Theranostics), School of Pharmacy, Tianjin Medical University, Tianjin, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics (Theranostics), School of Pharmacy, Tianjin Medical University, Tianjin</wicri:regionArea><placeName><settlement type="city">Tianjin</settlement></placeName></affiliation></author><author><name sortKey="Liu, Xing Hai" sort="Liu, Xing Hai" uniqKey="Liu X" first="Xing-Hai" last="Liu">Xing-Hai Liu</name><affiliation wicri:level="3"><nlm:affiliation>College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Chemical Engineering, Zhejiang University of Technology, Hangzhou</wicri:regionArea><placeName><settlement type="city">Hangzhou</settlement><region type="province">Zhejiang</region></placeName></affiliation></author></analytic><series><title level="j">Journal of enzyme inhibition and medicinal chemistry</title><idno type="eISSN">1475-6374</idno><imprint><date when="2020" type="published">2020</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>Antifungal Agents (chemical synthesis)</term><term>Antifungal Agents (chemistry)</term><term>Antifungal Agents (pharmacology)</term><term>Dose-Response Relationship, Drug (MeSH)</term><term>Drug Design (MeSH)</term><term>Fungi (drug effects)</term><term>Microbial Sensitivity Tests (MeSH)</term><term>Molecular Structure (MeSH)</term><term>Structure-Activity Relationship (MeSH)</term><term>Threonine (chemical synthesis)</term><term>Threonine (chemistry)</term><term>Threonine (pharmacology)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Amides (composition chimique)</term><term>Amides (pharmacologie)</term><term>Amides (synthèse chimique)</term><term>Antifongiques (composition chimique)</term><term>Antifongiques (pharmacologie)</term><term>Antifongiques (synthèse chimique)</term><term>Champignons (effets des médicaments et des substances chimiques)</term><term>Conception de médicament (MeSH)</term><term>Relation dose-effet des médicaments (MeSH)</term><term>Relation structure-activité (MeSH)</term><term>Structure moléculaire (MeSH)</term><term>Tests de sensibilité microbienne (MeSH)</term><term>Thréonine (composition chimique)</term><term>Thréonine (pharmacologie)</term><term>Thréonine (synthèse chimique)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Amides</term><term>Antifungal Agents</term><term>Threonine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Amides</term><term>Antifungal Agents</term><term>Threonine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Amides</term><term>Antifungal Agents</term><term>Threonine</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Amides</term><term>Antifongiques</term><term>Thréonine</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Fungi</term></keywords><keywords scheme="MESH" qualifier="effets des médicaments et des substances chimiques" xml:lang="fr"><term>Champignons</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Amides</term><term>Antifongiques</term><term>Thréonine</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Amides</term><term>Antifongiques</term><term>Thréonine</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Dose-Response Relationship, Drug</term><term>Drug Design</term><term>Microbial Sensitivity Tests</term><term>Molecular Structure</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Conception de médicament</term><term>Relation dose-effet des médicaments</term><term>Relation structure-activité</term><term>Structure moléculaire</term><term>Tests de sensibilité microbienne</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Thirty-six novel threoninamide carbamate derivatives were designed and synthesised using active fragment-based pharmacophore model. Antifungal activities of these compounds were tested against <i>Oomycete</i> fungi <i>Phytophthora capsici in vitro</i> and <i>in vivo.</i> Interestingly, compound <b>I-1, I-2, I-3, I-6</b> and <b>I-7</b> exhibited moderate control effect (>50%) against <i>Pseudoperonospora cubensis</i> in greenhouse at 6.25 μg/mL, which is better than that of control. Meanwhile most of these compounds exhibited significant inhibitory against <i>P. capsici</i>. The other nine fungi were also tested. More importantly, some compounds exhibited remarkably high activities against <i>Sclerotinia sclerotiorum</i>, <i>P. piricola</i> and <i>R. solan in vitro</i> with EC<sub>50</sub> values of 3.74-9.76 μg/mL. It is possible that the model is reliabile and this method can be used to discover lead compounds for the development of fungicides.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">32148108</PMID><DateCompleted><Year>2020</Year><Month>10</Month><Day>26</Day></DateCompleted><DateRevised><Year>2020</Year><Month>10</Month><Day>26</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Electronic">1475-6374</ISSN><JournalIssue CitedMedium="Internet"><Volume>35</Volume><Issue>1</Issue><PubDate><Year>2020</Year><Month>Dec</Month></PubDate></JournalIssue><Title>Journal of enzyme inhibition and medicinal chemistry</Title><ISOAbbreviation>J Enzyme Inhib Med Chem</ISOAbbreviation></Journal><ArticleTitle>Design, synthesis and antifungal activity of threoninamide carbamate derivatives via pharmacophore model.</ArticleTitle><Pagination><MedlinePgn>682-691</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1080/14756366.2020.1729144</ELocationID><Abstract><AbstractText>Thirty-six novel threoninamide carbamate derivatives were designed and synthesised using active fragment-based pharmacophore model. Antifungal activities of these compounds were tested against <i>Oomycete</i> fungi <i>Phytophthora capsici in vitro</i> and <i>in vivo.</i> Interestingly, compound <b>I-1, I-2, I-3, I-6</b> and <b>I-7</b> exhibited moderate control effect (>50%) against <i>Pseudoperonospora cubensis</i> in greenhouse at 6.25 μg/mL, which is better than that of control. Meanwhile most of these compounds exhibited significant inhibitory against <i>P. capsici</i>. The other nine fungi were also tested. More importantly, some compounds exhibited remarkably high activities against <i>Sclerotinia sclerotiorum</i>, <i>P. piricola</i> and <i>R. solan in vitro</i> with EC<sub>50</sub> values of 3.74-9.76 μg/mL. It is possible that the model is reliabile and this method can be used to discover lead compounds for the development of fungicides.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Du</LastName><ForeName>Xiu-Jiang</ForeName><Initials>XJ</Initials><AffiliationInfo><Affiliation>State Key Laboratory of Elemental Organic Chemistry, Nankai University, Tianjin, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Peng</LastName><ForeName>Xing-Jie</ForeName><Initials>XJ</Initials><AffiliationInfo><Affiliation>State Key Laboratory of Elemental Organic Chemistry, Nankai University, Tianjin, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zhao</LastName><ForeName>Rui-Qi</ForeName><Initials>RQ</Initials><AffiliationInfo><Affiliation>State Key Laboratory of Elemental Organic Chemistry, Nankai University, Tianjin, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zhao</LastName><ForeName>Wei-Guang</ForeName><Initials>WG</Initials><AffiliationInfo><Affiliation>State Key Laboratory of Elemental Organic Chemistry, Nankai University, Tianjin, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Dong</LastName><ForeName>Wei-Li</ForeName><Initials>WL</Initials><AffiliationInfo><Affiliation>Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics (Theranostics), School of Pharmacy, Tianjin Medical University, Tianjin, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Liu</LastName><ForeName>Xing-Hai</ForeName><Initials>XH</Initials><AffiliationInfo><Affiliation>College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, China.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>J Enzyme Inhib Med Chem</MedlineTA><NlmUniqueID>101150203</NlmUniqueID><ISSNLinking>1475-6366</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000577">Amides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000935">Antifungal Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>2ZD004190S</RegistryNumber><NameOfSubstance UI="D013912">Threonine</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000577" MajorTopicYN="N">Amides</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D000935" MajorTopicYN="N">Antifungal Agents</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004305" MajorTopicYN="N">Dose-Response Relationship, Drug</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015195" MajorTopicYN="Y">Drug Design</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D005658" MajorTopicYN="N">Fungi</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008826" MajorTopicYN="N">Microbial Sensitivity Tests</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013912" MajorTopicYN="N">Threonine</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="N">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Pharmacophore model</Keyword><Keyword MajorTopicYN="N">SAR</Keyword><Keyword MajorTopicYN="N">antifungal activity</Keyword><Keyword MajorTopicYN="N">synthesis</Keyword><Keyword MajorTopicYN="N">threoninamide carbamate derivatives</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="entrez"><Year>2020</Year><Month>3</Month><Day>10</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate 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IdType="pubmed">31050111</ArticleId></ArticleIdList></Reference></ReferenceList></PubmedData></pubmed><affiliations><list><country><li>République populaire de Chine</li></country><region><li>Zhejiang</li></region><settlement><li>Hangzhou</li><li>Tianjin</li></settlement></list><tree><country name="République populaire de Chine"><noRegion><name sortKey="Du, Xiu Jiang" sort="Du, Xiu Jiang" uniqKey="Du X" first="Xiu-Jiang" last="Du">Xiu-Jiang Du</name></noRegion><name sortKey="Dong, Wei Li" sort="Dong, Wei Li" uniqKey="Dong W" first="Wei-Li" last="Dong">Wei-Li Dong</name><name sortKey="Liu, Xing Hai" sort="Liu, Xing Hai" uniqKey="Liu X" first="Xing-Hai" last="Liu">Xing-Hai Liu</name><name sortKey="Peng, Xing Jie" sort="Peng, Xing Jie" uniqKey="Peng X" first="Xing-Jie" last="Peng">Xing-Jie Peng</name><name sortKey="Zhao, Rui Qi" sort="Zhao, Rui Qi" uniqKey="Zhao R" first="Rui-Qi" last="Zhao">Rui-Qi Zhao</name><name sortKey="Zhao, Wei Guang" sort="Zhao, Wei Guang" uniqKey="Zhao W" 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