Heterocyclic lactam derivatives containing piperonyl moiety as potential antifungal agents.
Identifieur interne : 000484 ( Main/Exploration ); précédent : 000483; suivant : 000485Heterocyclic lactam derivatives containing piperonyl moiety as potential antifungal agents.
Auteurs : Shuangshuang Wang [République populaire de Chine] ; Longzhu Bao [République populaire de Chine] ; Di Song [République populaire de Chine] ; Jingjing Wang [République populaire de Chine] ; Xiufang Cao [République populaire de Chine]Source :
- Bioorganic & medicinal chemistry letters [ 1464-3405 ] ; 2019.
Descripteurs français
- KwdFr :
- Alcools benzyliques (composition chimique), Antifongiques (pharmacologie), Antifongiques (synthèse chimique), Champignons (effets des médicaments et des substances chimiques), Conception de médicament (MeSH), Lactames (pharmacologie), Lactames (synthèse chimique), Maladies des plantes (microbiologie), Oxazoles (pharmacologie), Relation structure-activité (MeSH), Structure moléculaire (MeSH), Tests de sensibilité microbienne (MeSH).
- MESH :
- composition chimique : Alcools benzyliques.
- effets des médicaments et des substances chimiques : Champignons.
- microbiologie : Maladies des plantes.
- pharmacologie : Antifongiques, Lactames, Oxazoles.
- synthèse chimique : Antifongiques, Lactames.
- Conception de médicament, Relation structure-activité, Structure moléculaire, Tests de sensibilité microbienne.
English descriptors
- KwdEn :
- Antifungal Agents (chemical synthesis), Antifungal Agents (pharmacology), Benzyl Alcohols (chemistry), Drug Design (MeSH), Fungi (drug effects), Lactams (chemical synthesis), Lactams (pharmacology), Microbial Sensitivity Tests (MeSH), Molecular Structure (MeSH), Oxazoles (pharmacology), Plant Diseases (microbiology), Structure-Activity Relationship (MeSH).
- MESH :
- chemical , chemical synthesis : Antifungal Agents, Lactams.
- chemical , chemistry : Benzyl Alcohols.
- chemical , pharmacology : Antifungal Agents, Lactams, Oxazoles.
- drug effects : Fungi.
- microbiology : Plant Diseases.
- Drug Design, Microbial Sensitivity Tests, Molecular Structure, Structure-Activity Relationship.
Abstract
To study the novel functionalized heterocyclic molecules with highly potential biological activity, two series of heterocyclic lactam derivatives containing the piperonyl moiety were designed and synthesized. The newly obtained compounds have been identified on the basis of analytical spectral data, including 1H NMR, 13C NMR, and ESI-MS. The target compounds were evaluated for their potential antifungal activities in vitro against twelve species of the plant pathogen fungi (Sclerotinia sclerotiorum, Rhizoctonia solani, Rap Sclerotinia stemrot, Fusarium graminearum, Phomopsis adianticola, Pestallozzia theae, Pestalotiopsis guepinii, Alternaria tenuis Nees, Monilinia fructicola, Colletotrichum gloeosporioides, Phytophthora capsici, Magnaporthe oryzae). Preliminary bioassays suggested that all prepared compounds I1-14 displayed broad-spectrum and moderate antifungal activities compared with the positive control hymexazol, especially for Sclerotinia sclerotiorum, Rap Sclerotinia stemrot, and Monilinia fructicola. In particular, the inhibition rate of compound I9 exhibited good inhibition activity reached 95.16% against Sclerotinia sclerotiorum, and compounds I5, I12 against Phytophthora capsici were 93.44%, 91.25%. Further studies revealed that compounds I5 (IC50 = 19.13 µM) and I12 (IC50 = 9.12 µM) exhibited obviously antifungal activities against Phytophthora capsici, which were better than that of commercial agricultural fungicide hymexazol (IC50 = 325.45 µM). Therefore, these target compounds could be further studied and explored as a lead skeleton for discovery of novel antifungal agents.
DOI: 10.1016/j.bmcl.2019.126661
PubMed: 31515187
Affiliations:
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Electronic address: caoxiufang@mail.hzau.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Science, Huazhong Agricultural University, Wuhan 430070</wicri:regionArea><placeName><settlement type="city">Wuhan</settlement><region type="région">Hubei</region></placeName></affiliation></author></analytic><series><title level="j">Bioorganic & medicinal chemistry letters</title><idno type="eISSN">1464-3405</idno><imprint><date when="2019" type="published">2019</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antifungal Agents (chemical synthesis)</term><term>Antifungal Agents (pharmacology)</term><term>Benzyl Alcohols (chemistry)</term><term>Drug Design (MeSH)</term><term>Fungi (drug effects)</term><term>Lactams (chemical synthesis)</term><term>Lactams (pharmacology)</term><term>Microbial Sensitivity Tests (MeSH)</term><term>Molecular Structure (MeSH)</term><term>Oxazoles (pharmacology)</term><term>Plant Diseases (microbiology)</term><term>Structure-Activity Relationship (MeSH)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Alcools benzyliques (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>Lactames (pharmacologie)</term><term>Lactames (synthèse chimique)</term><term>Maladies des plantes (microbiologie)</term><term>Oxazoles (pharmacologie)</term><term>Relation structure-activité (MeSH)</term><term>Structure moléculaire (MeSH)</term><term>Tests de sensibilité microbienne (MeSH)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antifungal Agents</term><term>Lactams</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Benzyl Alcohols</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antifungal Agents</term><term>Lactams</term><term>Oxazoles</term></keywords><keywords scheme="MESH" qualifier="composition chimique" xml:lang="fr"><term>Alcools benzyliques</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="microbiologie" xml:lang="fr"><term>Maladies des plantes</term></keywords><keywords scheme="MESH" qualifier="microbiology" xml:lang="en"><term>Plant Diseases</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antifongiques</term><term>Lactames</term><term>Oxazoles</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antifongiques</term><term>Lactames</term></keywords><keywords scheme="MESH" xml:lang="en"><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 structure-activité</term><term>Structure moléculaire</term><term>Tests de sensibilité microbienne</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">To study the novel functionalized heterocyclic molecules with highly potential biological activity, two series of heterocyclic lactam derivatives containing the piperonyl moiety were designed and synthesized. The newly obtained compounds have been identified on the basis of analytical spectral data, including <sup>1</sup>H NMR, <sup>13</sup>C NMR, and ESI-MS. The target compounds were evaluated for their potential antifungal activities in vitro against twelve species of the plant pathogen fungi (Sclerotinia sclerotiorum, Rhizoctonia solani, Rap Sclerotinia stemrot, Fusarium graminearum, Phomopsis adianticola, Pestallozzia theae, Pestalotiopsis guepinii, Alternaria tenuis Nees, Monilinia fructicola, Colletotrichum gloeosporioides, Phytophthora capsici, Magnaporthe oryzae). Preliminary bioassays suggested that all prepared compounds I1-14 displayed broad-spectrum and moderate antifungal activities compared with the positive control hymexazol, especially for Sclerotinia sclerotiorum, Rap Sclerotinia stemrot, and Monilinia fructicola. In particular, the inhibition rate of compound I9 exhibited good inhibition activity reached 95.16% against Sclerotinia sclerotiorum, and compounds I5, I12 against Phytophthora capsici were 93.44%, 91.25%. Further studies revealed that compounds I5 (IC<sub>50</sub> = 19.13 µM) and I12 (IC<sub>50</sub> = 9.12 µM) exhibited obviously antifungal activities against Phytophthora capsici, which were better than that of commercial agricultural fungicide hymexazol (IC<sub>50</sub> = 325.45 µM). Therefore, these target compounds could be further studied and explored as a lead skeleton for discovery of novel antifungal agents.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">31515187</PMID><DateCompleted><Year>2020</Year><Month>10</Month><Day>22</Day></DateCompleted><DateRevised><Year>2020</Year><Month>10</Month><Day>22</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1464-3405</ISSN><JournalIssue CitedMedium="Internet"><Volume>29</Volume><Issue>20</Issue><PubDate><Year>2019</Year><Month>10</Month><Day>15</Day></PubDate></JournalIssue><Title>Bioorganic & medicinal chemistry letters</Title><ISOAbbreviation>Bioorg Med Chem Lett</ISOAbbreviation></Journal><ArticleTitle>Heterocyclic lactam derivatives containing piperonyl moiety as potential antifungal agents.</ArticleTitle><Pagination><MedlinePgn>126661</MedlinePgn></Pagination><ELocationID EIdType="pii" ValidYN="Y">S0960-894X(19)30611-0</ELocationID><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.bmcl.2019.126661</ELocationID><Abstract><AbstractText>To study the novel functionalized heterocyclic molecules with highly potential biological activity, two series of heterocyclic lactam derivatives containing the piperonyl moiety were designed and synthesized. The newly obtained compounds have been identified on the basis of analytical spectral data, including <sup>1</sup>H NMR, <sup>13</sup>C NMR, and ESI-MS. The target compounds were evaluated for their potential antifungal activities in vitro against twelve species of the plant pathogen fungi (Sclerotinia sclerotiorum, Rhizoctonia solani, Rap Sclerotinia stemrot, Fusarium graminearum, Phomopsis adianticola, Pestallozzia theae, Pestalotiopsis guepinii, Alternaria tenuis Nees, Monilinia fructicola, Colletotrichum gloeosporioides, Phytophthora capsici, Magnaporthe oryzae). Preliminary bioassays suggested that all prepared compounds I1-14 displayed broad-spectrum and moderate antifungal activities compared with the positive control hymexazol, especially for Sclerotinia sclerotiorum, Rap Sclerotinia stemrot, and Monilinia fructicola. In particular, the inhibition rate of compound I9 exhibited good inhibition activity reached 95.16% against Sclerotinia sclerotiorum, and compounds I5, I12 against Phytophthora capsici were 93.44%, 91.25%. Further studies revealed that compounds I5 (IC<sub>50</sub> = 19.13 µM) and I12 (IC<sub>50</sub> = 9.12 µM) exhibited obviously antifungal activities against Phytophthora capsici, which were better than that of commercial agricultural fungicide hymexazol (IC<sub>50</sub> = 325.45 µM). Therefore, these target compounds could be further studied and explored as a lead skeleton for discovery of novel antifungal agents.</AbstractText><CopyrightInformation>Copyright © 2019 Elsevier Ltd. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Wang</LastName><ForeName>Shuangshuang</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>College of Science, Huazhong Agricultural University, Wuhan 430070, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Bao</LastName><ForeName>Longzhu</ForeName><Initials>L</Initials><AffiliationInfo><Affiliation>College of Science, Huazhong Agricultural University, Wuhan 430070, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Song</LastName><ForeName>Di</ForeName><Initials>D</Initials><AffiliationInfo><Affiliation>College of Science, Huazhong Agricultural University, Wuhan 430070, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Wang</LastName><ForeName>Jingjing</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>College of Science, Huazhong Agricultural University, Wuhan 430070, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Cao</LastName><ForeName>Xiufang</ForeName><Initials>X</Initials><AffiliationInfo><Affiliation>College of Science, Huazhong Agricultural University, Wuhan 430070, China. Electronic address: caoxiufang@mail.hzau.edu.cn.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2019</Year><Month>09</Month><Day>03</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Bioorg Med Chem Lett</MedlineTA><NlmUniqueID>9107377</NlmUniqueID><ISSNLinking>0960-894X</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000935">Antifungal Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D001592">Benzyl Alcohols</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D007769">Lactams</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010080">Oxazoles</NameOfSubstance></Chemical><Chemical><RegistryNumber>20T2M875LO</RegistryNumber><NameOfSubstance UI="C531211">hymexazol</NameOfSubstance></Chemical><Chemical><RegistryNumber>4163K563GS</RegistryNumber><NameOfSubstance UI="C041611">piperonyl alcohol</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000935" MajorTopicYN="N">Antifungal Agents</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001592" MajorTopicYN="N">Benzyl Alcohols</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015195" MajorTopicYN="N">Drug Design</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D005658" MajorTopicYN="N">Fungi</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D007769" MajorTopicYN="N">Lactams</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</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="D010080" MajorTopicYN="N">Oxazoles</DescriptorName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010935" MajorTopicYN="N">Plant Diseases</DescriptorName><QualifierName UI="Q000382" MajorTopicYN="Y">microbiology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="Y">Antifungal activities</Keyword><Keyword MajorTopicYN="Y">Lactam</Keyword><Keyword MajorTopicYN="Y">Piperonyl</Keyword><Keyword MajorTopicYN="Y">Plant pathogenic fungi</Keyword><Keyword MajorTopicYN="Y">Synthesis</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2019</Year><Month>05</Month><Day>05</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2019</Year><Month>08</Month><Day>08</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2019</Year><Month>09</Month><Day>01</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2019</Year><Month>9</Month><Day>14</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>10</Month><Day>23</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2019</Year><Month>9</Month><Day>14</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">31515187</ArticleId><ArticleId IdType="pii">S0960-894X(19)30611-0</ArticleId><ArticleId IdType="doi">10.1016/j.bmcl.2019.126661</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>République populaire de Chine</li></country><region><li>Hubei</li></region><settlement><li>Wuhan</li></settlement></list><tree><country name="République populaire de Chine"><region name="Hubei"><name sortKey="Wang, Shuangshuang" sort="Wang, Shuangshuang" uniqKey="Wang S" first="Shuangshuang" last="Wang">Shuangshuang Wang</name></region><name sortKey="Bao, Longzhu" sort="Bao, Longzhu" uniqKey="Bao L" first="Longzhu" last="Bao">Longzhu Bao</name><name sortKey="Cao, Xiufang" sort="Cao, Xiufang" uniqKey="Cao X" first="Xiufang" last="Cao">Xiufang Cao</name><name sortKey="Song, Di" sort="Song, Di" uniqKey="Song D" first="Di" last="Song">Di Song</name><name sortKey="Wang, Jingjing" sort="Wang, Jingjing" uniqKey="Wang J" first="Jingjing" last="Wang">Jingjing Wang</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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