Novel N-Cycloalkylcarbonyl-N'-arylthioureas: Synthesis, Design, Antifungal Activity and Gene Toxicity.
Identifieur interne : 000104 ( Main/Exploration ); précédent : 000103; suivant : 000105Novel N-Cycloalkylcarbonyl-N'-arylthioureas: Synthesis, Design, Antifungal Activity and Gene Toxicity.
Auteurs : Olena V. Kholodniak [Ukraine, Allemagne] ; Maksym S. Kazunin [Ukraine] ; Fatuma Meyer [Allemagne] ; Sergiy I. Kovalenko [Ukraine] ; Karl G. Steffens [Allemagne]Source :
- Chemistry & biodiversity [ 1612-1880 ] ; 2020.
Abstract
A synthesis method of novel N-cycloalkylcarbonyl-N'-arylthioureas was developed. It consists of sequential addition of equimolecular amounts of ammonium isothiocyanate and substituted anilines to cycloalkylcarbonyl chlorides. The identity and purity of products were confirmed by LC/MS spectra, their structure by elemental analysis, IR and 1 H-NMR spectra. Preliminary antimicrobial screening for standard microorganisms and molecular docking allowed to select several structures for antifungal and genetic toxicity studies. Conducted in vitro screening of 9 compounds for antifungal potential against 11 phytopathogenic fungi and three Phytophthora strains revealed that two N-(arylcarbamothioyl) cyclopropanecarboxamides at a concentration of 50 μg/ml exhibited activities comparable to the standard antifungal agent 'Cyproconazole'. Analysis of mutagenicity of novel thioureas using the Salmonella reverse mutagenicity assay ('Ames Test') showed a low gene-toxicity profile.
DOI: 10.1002/cbdv.202000212
PubMed: 32372529
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Kholodniak</name><affiliation wicri:level="1"><nlm:affiliation>Zaporizhzhia State Medical University, Organic and Bioorganic Chemistry Department, Mayakovs'ky Ave. 26, 69035, Zaporizhzhia, Ukraine.</nlm:affiliation><country xml:lang="fr">Ukraine</country><wicri:regionArea>Zaporizhzhia State Medical University, Organic and Bioorganic Chemistry Department, Mayakovs'ky Ave. 26, 69035, Zaporizhzhia</wicri:regionArea><wicri:noRegion>Zaporizhzhia</wicri:noRegion></affiliation><affiliation wicri:level="1"><nlm:affiliation>Neubrandenburg University of Applied Sciences, Faculty of Agriculture and Food Science, Brodaer Str. 2, 17033, Neubrandenburg, Germany.</nlm:affiliation><country xml:lang="fr">Allemagne</country><wicri:regionArea>Neubrandenburg University of Applied Sciences, Faculty of Agriculture and Food Science, Brodaer Str. 2, 17033, Neubrandenburg</wicri:regionArea><wicri:noRegion>17033, Neubrandenburg</wicri:noRegion><wicri:noRegion>17033, Neubrandenburg</wicri:noRegion><wicri:noRegion>Neubrandenburg</wicri:noRegion></affiliation></author><author><name sortKey="Kazunin, Maksym S" sort="Kazunin, Maksym S" uniqKey="Kazunin M" first="Maksym S" last="Kazunin">Maksym S. Kazunin</name><affiliation wicri:level="1"><nlm:affiliation>Zaporizhzhia State Medical University, Organic and Bioorganic Chemistry Department, Mayakovs'ky Ave. 26, 69035, Zaporizhzhia, Ukraine.</nlm:affiliation><country xml:lang="fr">Ukraine</country><wicri:regionArea>Zaporizhzhia State Medical University, Organic and Bioorganic Chemistry Department, Mayakovs'ky Ave. 26, 69035, Zaporizhzhia</wicri:regionArea><wicri:noRegion>Zaporizhzhia</wicri:noRegion></affiliation></author><author><name sortKey="Meyer, Fatuma" sort="Meyer, Fatuma" uniqKey="Meyer F" first="Fatuma" last="Meyer">Fatuma Meyer</name><affiliation wicri:level="1"><nlm:affiliation>Neubrandenburg University of Applied Sciences, Faculty of Agriculture and Food Science, Brodaer Str. 2, 17033, Neubrandenburg, Germany.</nlm:affiliation><country xml:lang="fr">Allemagne</country><wicri:regionArea>Neubrandenburg University of Applied Sciences, Faculty of Agriculture and Food Science, Brodaer Str. 2, 17033, Neubrandenburg</wicri:regionArea><wicri:noRegion>17033, Neubrandenburg</wicri:noRegion><wicri:noRegion>17033, Neubrandenburg</wicri:noRegion><wicri:noRegion>Neubrandenburg</wicri:noRegion></affiliation></author><author><name sortKey="Kovalenko, Sergiy I" sort="Kovalenko, Sergiy I" uniqKey="Kovalenko S" first="Sergiy I" last="Kovalenko">Sergiy I. Kovalenko</name><affiliation wicri:level="1"><nlm:affiliation>Zaporizhzhia State Medical University, Organic and Bioorganic Chemistry Department, Mayakovs'ky Ave. 26, 69035, Zaporizhzhia, Ukraine.</nlm:affiliation><country xml:lang="fr">Ukraine</country><wicri:regionArea>Zaporizhzhia State Medical University, Organic and Bioorganic Chemistry Department, Mayakovs'ky Ave. 26, 69035, Zaporizhzhia</wicri:regionArea><wicri:noRegion>Zaporizhzhia</wicri:noRegion></affiliation></author><author><name sortKey="Steffens, Karl G" sort="Steffens, Karl G" uniqKey="Steffens K" first="Karl G" last="Steffens">Karl G. Steffens</name><affiliation wicri:level="1"><nlm:affiliation>Neubrandenburg University of Applied Sciences, Faculty of Agriculture and Food Science, Brodaer Str. 2, 17033, Neubrandenburg, Germany.</nlm:affiliation><country xml:lang="fr">Allemagne</country><wicri:regionArea>Neubrandenburg University of Applied Sciences, Faculty of Agriculture and Food Science, Brodaer Str. 2, 17033, Neubrandenburg</wicri:regionArea><wicri:noRegion>17033, Neubrandenburg</wicri:noRegion><wicri:noRegion>17033, Neubrandenburg</wicri:noRegion><wicri:noRegion>Neubrandenburg</wicri:noRegion></affiliation></author></analytic><series><title level="j">Chemistry & biodiversity</title><idno type="eISSN">1612-1880</idno><imprint><date when="2020" type="published">2020</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A synthesis method of novel N-cycloalkylcarbonyl-N'-arylthioureas was developed. It consists of sequential addition of equimolecular amounts of ammonium isothiocyanate and substituted anilines to cycloalkylcarbonyl chlorides. The identity and purity of products were confirmed by LC/MS spectra, their structure by elemental analysis, IR and <sup>1</sup> H-NMR spectra. Preliminary antimicrobial screening for standard microorganisms and molecular docking allowed to select several structures for antifungal and genetic toxicity studies. Conducted in vitro screening of 9 compounds for antifungal potential against 11 phytopathogenic fungi and three Phytophthora strains revealed that two N-(arylcarbamothioyl) cyclopropanecarboxamides at a concentration of 50 μg/ml exhibited activities comparable to the standard antifungal agent 'Cyproconazole'. Analysis of mutagenicity of novel thioureas using the Salmonella reverse mutagenicity assay ('Ames Test') showed a low gene-toxicity profile.</div></front></TEI><pubmed><MedlineCitation Status="In-Process" Owner="NLM"><PMID Version="1">32372529</PMID><DateRevised><Year>2020</Year><Month>11</Month><Day>04</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1612-1880</ISSN><JournalIssue CitedMedium="Internet"><Volume>17</Volume><Issue>7</Issue><PubDate><Year>2020</Year><Month>Jul</Month></PubDate></JournalIssue><Title>Chemistry & biodiversity</Title><ISOAbbreviation>Chem Biodivers</ISOAbbreviation></Journal><ArticleTitle>Novel N-Cycloalkylcarbonyl-N'-arylthioureas: Synthesis, Design, Antifungal Activity and Gene Toxicity.</ArticleTitle><Pagination><MedlinePgn>e2000212</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1002/cbdv.202000212</ELocationID><Abstract><AbstractText>A synthesis method of novel N-cycloalkylcarbonyl-N'-arylthioureas was developed. It consists of sequential addition of equimolecular amounts of ammonium isothiocyanate and substituted anilines to cycloalkylcarbonyl chlorides. The identity and purity of products were confirmed by LC/MS spectra, their structure by elemental analysis, IR and <sup>1</sup> H-NMR spectra. Preliminary antimicrobial screening for standard microorganisms and molecular docking allowed to select several structures for antifungal and genetic toxicity studies. Conducted in vitro screening of 9 compounds for antifungal potential against 11 phytopathogenic fungi and three Phytophthora strains revealed that two N-(arylcarbamothioyl) cyclopropanecarboxamides at a concentration of 50 μg/ml exhibited activities comparable to the standard antifungal agent 'Cyproconazole'. Analysis of mutagenicity of novel thioureas using the Salmonella reverse mutagenicity assay ('Ames Test') showed a low gene-toxicity profile.</AbstractText><CopyrightInformation>© 2020 Wiley-VHCA AG, Zurich, Switzerland.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Kholodniak</LastName><ForeName>Olena V</ForeName><Initials>OV</Initials><Identifier Source="ORCID">http://orcid.org/0000-0002-0518-4262</Identifier><AffiliationInfo><Affiliation>Zaporizhzhia State Medical University, Organic and Bioorganic Chemistry Department, Mayakovs'ky Ave. 26, 69035, Zaporizhzhia, Ukraine.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Neubrandenburg University of Applied Sciences, Faculty of Agriculture and Food Science, Brodaer Str. 2, 17033, Neubrandenburg, Germany.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kazunin</LastName><ForeName>Maksym S</ForeName><Initials>MS</Initials><Identifier Source="ORCID">http://orcid.org/0000-0003-2562-8665</Identifier><AffiliationInfo><Affiliation>Zaporizhzhia State Medical University, Organic and Bioorganic Chemistry Department, Mayakovs'ky Ave. 26, 69035, Zaporizhzhia, Ukraine.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Meyer</LastName><ForeName>Fatuma</ForeName><Initials>F</Initials><AffiliationInfo><Affiliation>Neubrandenburg University of Applied Sciences, Faculty of Agriculture and Food Science, Brodaer Str. 2, 17033, Neubrandenburg, Germany.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kovalenko</LastName><ForeName>Sergiy I</ForeName><Initials>SI</Initials><Identifier Source="ORCID">http://orcid.org/0000-0001-8017-9108</Identifier><AffiliationInfo><Affiliation>Zaporizhzhia State Medical University, Organic and Bioorganic Chemistry Department, Mayakovs'ky Ave. 26, 69035, Zaporizhzhia, Ukraine.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Steffens</LastName><ForeName>Karl G</ForeName><Initials>KG</Initials><AffiliationInfo><Affiliation>Neubrandenburg University of Applied Sciences, Faculty of Agriculture and Food Science, Brodaer Str. 2, 17033, Neubrandenburg, Germany.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2020</Year><Month>06</Month><Day>23</Day></ArticleDate></Article><MedlineJournalInfo><Country>Switzerland</Country><MedlineTA>Chem Biodivers</MedlineTA><NlmUniqueID>101197449</NlmUniqueID><ISSNLinking>1612-1872</ISSNLinking></MedlineJournalInfo><CitationSubset>IM</CitationSubset><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">N-cycloalkylcarbonyl-N′-arylthioureas</Keyword><Keyword MajorTopicYN="N">gene toxicity</Keyword><Keyword MajorTopicYN="N">mutagenicity</Keyword><Keyword MajorTopicYN="N">spectral data, anti-phytopathogens</Keyword><Keyword MajorTopicYN="N">synthesis</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2020</Year><Month>03</Month><Day>30</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2020</Year><Month>05</Month><Day>05</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2020</Year><Month>5</Month><Day>7</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>5</Month><Day>7</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2020</Year><Month>5</Month><Day>7</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">32372529</ArticleId><ArticleId IdType="doi">10.1002/cbdv.202000212</ArticleId></ArticleIdList><ReferenceList><Reference><Citation>M. 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Kovalenko</name></country><country name="Allemagne"><noRegion><name sortKey="Kholodniak, Olena V" sort="Kholodniak, Olena V" uniqKey="Kholodniak O" first="Olena V" last="Kholodniak">Olena V. Kholodniak</name></noRegion><name sortKey="Meyer, Fatuma" sort="Meyer, Fatuma" uniqKey="Meyer F" first="Fatuma" last="Meyer">Fatuma Meyer</name><name sortKey="Steffens, Karl G" sort="Steffens, Karl G" uniqKey="Steffens K" first="Karl G" last="Steffens">Karl G. Steffens</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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