PhytophthoraV1, Main, Exploration, bibRecord, 000657

Synthesis and Fungicidal Activity of Lansiumamide A and B and Their Derivatives.

Identifieur interne : 000657 ( Main/Exploration ); précédent : 000656; suivant : 000658

Synthesis and Fungicidal Activity of Lansiumamide A and B and Their Derivatives.

Auteurs : Huiyou Xu [République populaire de Chine] ; Ting Chen [République populaire de Chine] ; Luanbin Huang [République populaire de Chine] ; Qiuju Shen [République populaire de Chine] ; Zengwei Lian [République populaire de Chine] ; Yan Shi [République populaire de Chine] ; Ming-An Ouyang [République populaire de Chine] ; Liyan Song [République populaire de Chine]

Source :

Molecules (Basel, Switzerland) [ 1420-3049 ] ; 2018.

RBID : pubmed:29933580

Descripteurs français

KwdFr :
- Alkylation (MeSH), Ascomycota (croissance et développement), Ascomycota (effets des médicaments et des substances chimiques), Botrytis (croissance et développement), Botrytis (effets des médicaments et des substances chimiques), Cinnamates (pharmacologie), Cinnamates (synthèse chimique), Esters (MeSH), Fongicides industriels (pharmacologie), Fongicides industriels (synthèse chimique), Fusarium (croissance et développement), Fusarium (effets des médicaments et des substances chimiques), Phytophthora (croissance et développement), Phytophthora (effets des médicaments et des substances chimiques), Relation structure-activité (MeSH), Styrènes (pharmacologie), Styrènes (synthèse chimique), Tests de sensibilité microbienne (MeSH).
MESH :
- croissance et développement : Ascomycota, Botrytis, Fusarium, Phytophthora.
- effets des médicaments et des substances chimiques : Ascomycota, Botrytis, Fusarium, Phytophthora.
- pharmacologie : Cinnamates, Fongicides industriels, Styrènes.
- synthèse chimique : Cinnamates, Fongicides industriels, Styrènes.
- Alkylation, Esters, Relation structure-activité, Tests de sensibilité microbienne.

English descriptors

KwdEn :
- Alkylation (MeSH), Ascomycota (drug effects), Ascomycota (growth & development), Botrytis (drug effects), Botrytis (growth & development), Cinnamates (chemical synthesis), Cinnamates (pharmacology), Esters (MeSH), Fungicides, Industrial (chemical synthesis), Fungicides, Industrial (pharmacology), Fusarium (drug effects), Fusarium (growth & development), Microbial Sensitivity Tests (MeSH), Phytophthora (drug effects), Phytophthora (growth & development), Structure-Activity Relationship (MeSH), Styrenes (chemical synthesis), Styrenes (pharmacology).
MESH :
- chemical , chemical synthesis : Cinnamates, Fungicides, Industrial, Styrenes.
- drug effects : Ascomycota, Botrytis, Fusarium, Phytophthora.
- growth & development : Ascomycota, Botrytis, Fusarium, Phytophthora.
- chemical , pharmacology : Cinnamates, Fungicides, Industrial, Styrenes.
- Alkylation, Esters, Microbial Sensitivity Tests, Structure-Activity Relationship.

Abstract

A efficient 2-step protocol has been applied for the synthesis of Lansiumamide B (N-methyl-N-cis-styryl-cinnamamide, 2) derivatives by various substitution on the amide nitrogen with alkyl, allyl, propargyl, benzyl or ester groups. The structures of nine new compounds were characterized by HRMS, ¹H NMR, and ¹³C NMR spectra. These compounds were tested in vitro against 10 strains of phytopathogenic fungi and showed a wide antifungal spectrum. The relationship between different substituents on the amide nitrogen and antifungal activity of Lansiumamide B derivatives were compared and analyzed. The result indicates that the length and steric hindrance of N-substitution have a significant impact on biological activities. It is noteworthy that the methyl or ethyl substituent on the amide nitrogen is critical for the antifungal activities.

DOI: 10.3390/molecules23071499
PubMed: 29933580
PubMed Central: PMC6099640

Affiliations:

Links toward previous steps (curation, corpus...)

to stream Main, to step Corpus: 000733
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Le document en format XML

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</placeName>
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<author><name sortKey="Lian, Zengwei" sort="Lian, Zengwei" uniqKey="Lian Z" first="Zengwei" last="Lian">Zengwei Lian</name>
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Alkylation (MeSH)</term>
<term>Ascomycota (drug effects)</term>
<term>Ascomycota (growth & development)</term>
<term>Botrytis (drug effects)</term>
<term>Botrytis (growth & development)</term>
<term>Cinnamates (chemical synthesis)</term>
<term>Cinnamates (pharmacology)</term>
<term>Esters (MeSH)</term>
<term>Fungicides, Industrial (chemical synthesis)</term>
<term>Fungicides, Industrial (pharmacology)</term>
<term>Fusarium (drug effects)</term>
<term>Fusarium (growth & development)</term>
<term>Microbial Sensitivity Tests (MeSH)</term>
<term>Phytophthora (drug effects)</term>
<term>Phytophthora (growth & development)</term>
<term>Structure-Activity Relationship (MeSH)</term>
<term>Styrenes (chemical synthesis)</term>
<term>Styrenes (pharmacology)</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Alkylation (MeSH)</term>
<term>Ascomycota (croissance et développement)</term>
<term>Ascomycota (effets des médicaments et des substances chimiques)</term>
<term>Botrytis (croissance et développement)</term>
<term>Botrytis (effets des médicaments et des substances chimiques)</term>
<term>Cinnamates (pharmacologie)</term>
<term>Cinnamates (synthèse chimique)</term>
<term>Esters (MeSH)</term>
<term>Fongicides industriels (pharmacologie)</term>
<term>Fongicides industriels (synthèse chimique)</term>
<term>Fusarium (croissance et développement)</term>
<term>Fusarium (effets des médicaments et des substances chimiques)</term>
<term>Phytophthora (croissance et développement)</term>
<term>Phytophthora (effets des médicaments et des substances chimiques)</term>
<term>Relation structure-activité (MeSH)</term>
<term>Styrènes (pharmacologie)</term>
<term>Styrènes (synthèse chimique)</term>
<term>Tests de sensibilité microbienne (MeSH)</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Cinnamates</term>
<term>Fungicides, Industrial</term>
<term>Styrenes</term>
</keywords>
<keywords scheme="MESH" qualifier="croissance et développement" xml:lang="fr"><term>Ascomycota</term>
<term>Botrytis</term>
<term>Fusarium</term>
<term>Phytophthora</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Ascomycota</term>
<term>Botrytis</term>
<term>Fusarium</term>
<term>Phytophthora</term>
</keywords>
<keywords scheme="MESH" qualifier="effets des médicaments et des substances chimiques" xml:lang="fr"><term>Ascomycota</term>
<term>Botrytis</term>
<term>Fusarium</term>
<term>Phytophthora</term>
</keywords>
<keywords scheme="MESH" qualifier="growth & development" xml:lang="en"><term>Ascomycota</term>
<term>Botrytis</term>
<term>Fusarium</term>
<term>Phytophthora</term>
</keywords>
<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Cinnamates</term>
<term>Fongicides industriels</term>
<term>Styrènes</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Cinnamates</term>
<term>Fungicides, Industrial</term>
<term>Styrenes</term>
</keywords>
<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Cinnamates</term>
<term>Fongicides industriels</term>
<term>Styrènes</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Alkylation</term>
<term>Esters</term>
<term>Microbial Sensitivity Tests</term>
<term>Structure-Activity Relationship</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Alkylation</term>
<term>Esters</term>
<term>Relation structure-activité</term>
<term>Tests de sensibilité microbienne</term>
</keywords>
</textClass>
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<front><div type="abstract" xml:lang="en">A efficient 2-step protocol has been applied for the synthesis of Lansiumamide B (<i>N</i>
-methyl-<i>N</i>
-<i>cis</i>
-styryl-cinnamamide, <b>2</b>
) derivatives by various substitution on the amide nitrogen with alkyl, allyl, propargyl, benzyl or ester groups. The structures of nine new compounds were characterized by HRMS, ¹H NMR, and <sup>13</sup>
C NMR spectra. These compounds were tested in vitro against 10 strains of phytopathogenic fungi and showed a wide antifungal spectrum. The relationship between different substituents on the amide nitrogen and antifungal activity of Lansiumamide B derivatives were compared and analyzed. The result indicates that the length and steric hindrance of <i>N</i>
-substitution have a significant impact on biological activities. It is noteworthy that the methyl or ethyl substituent on the amide nitrogen is critical for the antifungal activities.</div>
</front>
</TEI>
<pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">29933580</PMID>
<DateCompleted><Year>2018</Year>
<Month>10</Month>
<Day>15</Day>
</DateCompleted>
<DateRevised><Year>2018</Year>
<Month>12</Month>
<Day>07</Day>
</DateRevised>
<Article PubModel="Electronic"><Journal><ISSN IssnType="Electronic">1420-3049</ISSN>
<JournalIssue CitedMedium="Internet"><Volume>23</Volume>
<Issue>7</Issue>
<PubDate><Year>2018</Year>
<Month>Jun</Month>
<Day>21</Day>
</PubDate>
</JournalIssue>
<Title>Molecules (Basel, Switzerland)</Title>
<ISOAbbreviation>Molecules</ISOAbbreviation>
</Journal>
<ArticleTitle>Synthesis and Fungicidal Activity of Lansiumamide A and B and Their Derivatives.</ArticleTitle>
<ELocationID EIdType="pii" ValidYN="Y">E1499</ELocationID>
<ELocationID EIdType="doi" ValidYN="Y">10.3390/molecules23071499</ELocationID>
<Abstract><AbstractText>A efficient 2-step protocol has been applied for the synthesis of Lansiumamide B (<i>N</i>
-methyl-<i>N</i>
-<i>cis</i>
-styryl-cinnamamide, <b>2</b>
) derivatives by various substitution on the amide nitrogen with alkyl, allyl, propargyl, benzyl or ester groups. The structures of nine new compounds were characterized by HRMS, ¹H NMR, and <sup>13</sup>
C NMR spectra. These compounds were tested in vitro against 10 strains of phytopathogenic fungi and showed a wide antifungal spectrum. The relationship between different substituents on the amide nitrogen and antifungal activity of Lansiumamide B derivatives were compared and analyzed. The result indicates that the length and steric hindrance of <i>N</i>
-substitution have a significant impact on biological activities. It is noteworthy that the methyl or ethyl substituent on the amide nitrogen is critical for the antifungal activities.</AbstractText>
</Abstract>
<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Xu</LastName>
<ForeName>Huiyou</ForeName>
<Initials>H</Initials>
<AffiliationInfo><Affiliation>Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China. huiyouxu@126.com.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Chen</LastName>
<ForeName>Ting</ForeName>
<Initials>T</Initials>
<AffiliationInfo><Affiliation>Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China. fafuchenting@163.com.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Huang</LastName>
<ForeName>Luanbin</ForeName>
<Initials>L</Initials>
<AffiliationInfo><Affiliation>Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China. h17746075243@163.com.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Shen</LastName>
<ForeName>Qiuju</ForeName>
<Initials>Q</Initials>
<AffiliationInfo><Affiliation>Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China. m18759775477@163.com.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Lian</LastName>
<ForeName>Zengwei</ForeName>
<Initials>Z</Initials>
<AffiliationInfo><Affiliation>Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China. fafuzengweilian@126.com.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Shi</LastName>
<ForeName>Yan</ForeName>
<Initials>Y</Initials>
<AffiliationInfo><Affiliation>Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China. shiyanshelly@163.com.</Affiliation>
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<Author ValidYN="Y"><LastName>Ouyang</LastName>
<ForeName>Ming-An</ForeName>
<Initials>MA</Initials>
<AffiliationInfo><Affiliation>Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China. minganouyang@163.com.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Song</LastName>
<ForeName>Liyan</ForeName>
<Initials>L</Initials>
<AffiliationInfo><Affiliation>Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China. songliyan@fafu.edu.cn.</Affiliation>
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<ArticleDate DateType="Electronic"><Year>2018</Year>
<Month>06</Month>
<Day>21</Day>
</ArticleDate>
</Article>
<MedlineJournalInfo><Country>Switzerland</Country>
<MedlineTA>Molecules</MedlineTA>
<NlmUniqueID>100964009</NlmUniqueID>
<ISSNLinking>1420-3049</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList><Chemical><RegistryNumber>0</RegistryNumber>
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<Chemical><RegistryNumber>0</RegistryNumber>
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<Chemical><RegistryNumber>0</RegistryNumber>
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<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="C000593604">N-methyl-N-styrylcinnamamide</NameOfSubstance>
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<Chemical><RegistryNumber>0</RegistryNumber>
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</MeshHeading>
<MeshHeading><DescriptorName UI="D001203" MajorTopicYN="N">Ascomycota</DescriptorName>
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<QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName>
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</MeshHeading>
<MeshHeading><DescriptorName UI="D008826" MajorTopicYN="N">Microbial Sensitivity Tests</DescriptorName>
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<QualifierName UI="Q000254" MajorTopicYN="N">growth & development</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName>
</MeshHeading>
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<QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName>
</MeshHeading>
</MeshHeadingList>
<KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Lansiumamide B</Keyword>
<Keyword MajorTopicYN="N">SAR</Keyword>
<Keyword MajorTopicYN="N">antifungal activity</Keyword>
<Keyword MajorTopicYN="N">chemical synthesis</Keyword>
<Keyword MajorTopicYN="N">derivatives</Keyword>
</KeywordList>
</MedlineCitation>
<PubmedData><History><PubMedPubDate PubStatus="received"><Year>2018</Year>
<Month>05</Month>
<Day>29</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="revised"><Year>2018</Year>
<Month>06</Month>
<Day>12</Day>
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<PubMedPubDate PubStatus="accepted"><Year>2018</Year>
<Month>06</Month>
<Day>21</Day>
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<PubMedPubDate PubStatus="entrez"><Year>2018</Year>
<Month>6</Month>
<Day>24</Day>
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<PubMedPubDate PubStatus="medline"><Year>2018</Year>
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</ReferenceList>
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<affiliations><list><country><li>République populaire de Chine</li>
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<region><li>Fujian</li>
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<settlement><li>Fuzhou</li>
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<tree><country name="République populaire de Chine"><region name="Fujian"><name sortKey="Xu, Huiyou" sort="Xu, Huiyou" uniqKey="Xu H" first="Huiyou" last="Xu">Huiyou Xu</name>
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<name sortKey="Chen, Ting" sort="Chen, Ting" uniqKey="Chen T" first="Ting" last="Chen">Ting Chen</name>
<name sortKey="Huang, Luanbin" sort="Huang, Luanbin" uniqKey="Huang L" first="Luanbin" last="Huang">Luanbin Huang</name>
<name sortKey="Lian, Zengwei" sort="Lian, Zengwei" uniqKey="Lian Z" first="Zengwei" last="Lian">Zengwei Lian</name>
<name sortKey="Ouyang, Ming An" sort="Ouyang, Ming An" uniqKey="Ouyang M" first="Ming-An" last="Ouyang">Ming-An Ouyang</name>
<name sortKey="Shen, Qiuju" sort="Shen, Qiuju" uniqKey="Shen Q" first="Qiuju" last="Shen">Qiuju Shen</name>
<name sortKey="Shi, Yan" sort="Shi, Yan" uniqKey="Shi Y" first="Yan" last="Shi">Yan Shi</name>
<name sortKey="Song, Liyan" sort="Song, Liyan" uniqKey="Song L" first="Liyan" last="Song">Liyan Song</name>
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Synthesis and Fungicidal Activity of Lansiumamide A and B and Their Derivatives.

Synthesis and Fungicidal Activity of Lansiumamide A and B and Their Derivatives.

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