Design, Synthesis and Antifungal Activities of 6‐Substituted 3‐Butylphthalide Derivatives against Phytopathogenic Fungi
In order to discover novel potential antifungal agents, a series of 6‐substituted 3‐butylphthalide derivatives were designed, synthesized and evaluated for their antifungal activities against nine phytopathogenic fungi. Preliminary bioassay tests showed that five 3‐butylphthalide derivatives exhibit...
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| Veröffentlicht in: | Chemistry & biodiversity 2020-10, Vol.17 (10), p.e2000435-n/a |
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| creator | Li, Yong Luo, Zhongfu Luo, Bilan Lan, Qing Fan, Judi Xue, Wei Miao, Jing Li, Yi Tang, Lei Fan, Lingling |
| description | In order to discover novel potential antifungal agents, a series of 6‐substituted 3‐butylphthalide derivatives were designed, synthesized and evaluated for their antifungal activities against nine phytopathogenic fungi. Preliminary bioassay tests showed that five 3‐butylphthalide derivatives exhibited more potent antifungal activities than hymexazol at the concentration of 50 μg/mL. Especially, 3‐butyl‐6‐nitro‐2‐benzofuran‐1(3H)‐one and 3‐butyl‐6‐hydroxy‐5‐nitro‐2‐benzofuran‐1(3H)‐one had significant fungicidal activity against some phytopathogenic fungi. The EC50 of 3‐butyl‐6‐nitro‐2‐benzofuran‐1(3H)‐one against FS, FO and FG were 6.6, 9.6 and 16.0 μg/mL, respectively. The EC50 of 3‐butyl‐6‐hydroxy‐5‐nitro‐2‐benzofuran‐1(3H)‐one against BC, PO, VM, SS and AS were 6.3, 5.9, 10.0, 4.5 and 8.4 μg/mL, respectively. The preliminary structure–activity relationships (SARs) of all target compounds were also investigated. |
| doi_str_mv | 10.1002/cbdv.202000435 |
| format | Article |
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Preliminary bioassay tests showed that five 3‐butylphthalide derivatives exhibited more potent antifungal activities than hymexazol at the concentration of 50 μg/mL. Especially, 3‐butyl‐6‐nitro‐2‐benzofuran‐1(3H)‐one and 3‐butyl‐6‐hydroxy‐5‐nitro‐2‐benzofuran‐1(3H)‐one had significant fungicidal activity against some phytopathogenic fungi. The EC50 of 3‐butyl‐6‐nitro‐2‐benzofuran‐1(3H)‐one against FS, FO and FG were 6.6, 9.6 and 16.0 μg/mL, respectively. The EC50 of 3‐butyl‐6‐hydroxy‐5‐nitro‐2‐benzofuran‐1(3H)‐one against BC, PO, VM, SS and AS were 6.3, 5.9, 10.0, 4.5 and 8.4 μg/mL, respectively. The preliminary structure–activity relationships (SARs) of all target compounds were also investigated.</description><identifier>ISSN: 1612-1872</identifier><identifier>EISSN: 1612-1880</identifier><identifier>DOI: 10.1002/cbdv.202000435</identifier><identifier>PMID: 32687253</identifier><language>eng</language><publisher>Switzerland: Wiley Subscription Services, Inc</publisher><subject>Antifungal activity ; Antifungal agents ; Antifungal Agents - chemical synthesis ; Antifungal Agents - chemistry ; Antifungal Agents - pharmacology ; Apium - chemistry ; Benzofuran ; Benzofurans - chemical synthesis ; Benzofurans - chemistry ; Benzofurans - pharmacology ; Bioassays ; butylphthalide derivatives ; Derivatives ; Drug Design ; Fungi ; Fungi - drug effects ; Fungicidal activity ; Fungicides ; Ligusticum - chemistry ; Microbial Sensitivity Tests ; Molecular Structure ; Phytopathogenic fungi ; Seeds - chemistry ; Structure-Activity Relationship ; Substitutes ; synthesis</subject><ispartof>Chemistry & biodiversity, 2020-10, Vol.17 (10), p.e2000435-n/a</ispartof><rights>2020 Wiley‐VHCA AG, Zurich, Switzerland</rights><rights>2020 Wiley-VHCA AG, Zurich, Switzerland.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3735-385c04ca83f33e9a712f1cb7a2672796d60a31f17d59c331c54ad826d5e566dc3</citedby><cites>FETCH-LOGICAL-c3735-385c04ca83f33e9a712f1cb7a2672796d60a31f17d59c331c54ad826d5e566dc3</cites><orcidid>0000-0001-5607-3813</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbdv.202000435$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbdv.202000435$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32687253$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Yong</creatorcontrib><creatorcontrib>Luo, Zhongfu</creatorcontrib><creatorcontrib>Luo, Bilan</creatorcontrib><creatorcontrib>Lan, Qing</creatorcontrib><creatorcontrib>Fan, Judi</creatorcontrib><creatorcontrib>Xue, Wei</creatorcontrib><creatorcontrib>Miao, Jing</creatorcontrib><creatorcontrib>Li, Yi</creatorcontrib><creatorcontrib>Tang, Lei</creatorcontrib><creatorcontrib>Fan, Lingling</creatorcontrib><title>Design, Synthesis and Antifungal Activities of 6‐Substituted 3‐Butylphthalide Derivatives against Phytopathogenic Fungi</title><title>Chemistry & biodiversity</title><addtitle>Chem Biodivers</addtitle><description>In order to discover novel potential antifungal agents, a series of 6‐substituted 3‐butylphthalide derivatives were designed, synthesized and evaluated for their antifungal activities against nine phytopathogenic fungi. Preliminary bioassay tests showed that five 3‐butylphthalide derivatives exhibited more potent antifungal activities than hymexazol at the concentration of 50 μg/mL. Especially, 3‐butyl‐6‐nitro‐2‐benzofuran‐1(3H)‐one and 3‐butyl‐6‐hydroxy‐5‐nitro‐2‐benzofuran‐1(3H)‐one had significant fungicidal activity against some phytopathogenic fungi. The EC50 of 3‐butyl‐6‐nitro‐2‐benzofuran‐1(3H)‐one against FS, FO and FG were 6.6, 9.6 and 16.0 μg/mL, respectively. The EC50 of 3‐butyl‐6‐hydroxy‐5‐nitro‐2‐benzofuran‐1(3H)‐one against BC, PO, VM, SS and AS were 6.3, 5.9, 10.0, 4.5 and 8.4 μg/mL, respectively. The preliminary structure–activity relationships (SARs) of all target compounds were also investigated.</description><subject>Antifungal activity</subject><subject>Antifungal agents</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>Apium - chemistry</subject><subject>Benzofuran</subject><subject>Benzofurans - chemical synthesis</subject><subject>Benzofurans - chemistry</subject><subject>Benzofurans - pharmacology</subject><subject>Bioassays</subject><subject>butylphthalide derivatives</subject><subject>Derivatives</subject><subject>Drug Design</subject><subject>Fungi</subject><subject>Fungi - drug effects</subject><subject>Fungicidal activity</subject><subject>Fungicides</subject><subject>Ligusticum - chemistry</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Phytopathogenic fungi</subject><subject>Seeds - chemistry</subject><subject>Structure-Activity Relationship</subject><subject>Substitutes</subject><subject>synthesis</subject><issn>1612-1872</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkctKAzEUhoMoVqtblxJw48LWXCaZmWUvVgVBwct2SJNMJ2WaqZNMZXDjI_iMPomRagU3rnJy-P6PAz8ARxj1MULkXE7Vqk8QQQhFlG2BPcwx6eEkQdubOSYdsO_cPPBhn-yCDiU8bBndA69j7czMnsH71voizA4Kq-DAepM3diZKOJDerIw32sEqh_zj7f2-mTpvfOO1gjT8h41vy2XhC1EapeFY12YlQigkxEwY6zy8K1pfLYUvqpm2RsJJcJsDsJOL0unD77cLHicXD6Or3s3t5fVocNOTNKasRxMmUSRFQnNKdSpiTHIsp7EgPCZxyhVHguIcx4qlklIsWSRUQrhimnGuJO2C07V3WVfPjXY-WxgndVkKq6vGZSQijCUpJ2lAT_6g86qpbbguUCzilPEIBaq_pmRdOVfrPFvWZiHqNsMo-6ol-6ol29QSAsff2ma60GqD__QQgHQNvJhSt__ostFw_PQr_wSoPJv0</recordid><startdate>202010</startdate><enddate>202010</enddate><creator>Li, Yong</creator><creator>Luo, Zhongfu</creator><creator>Luo, Bilan</creator><creator>Lan, Qing</creator><creator>Fan, Judi</creator><creator>Xue, Wei</creator><creator>Miao, Jing</creator><creator>Li, Yi</creator><creator>Tang, Lei</creator><creator>Fan, Lingling</creator><general>Wiley Subscription Services, Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-5607-3813</orcidid></search><sort><creationdate>202010</creationdate><title>Design, Synthesis and Antifungal Activities of 6‐Substituted 3‐Butylphthalide Derivatives against Phytopathogenic Fungi</title><author>Li, Yong ; Luo, Zhongfu ; Luo, Bilan ; Lan, Qing ; Fan, Judi ; Xue, Wei ; Miao, Jing ; Li, Yi ; Tang, Lei ; Fan, Lingling</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3735-385c04ca83f33e9a712f1cb7a2672796d60a31f17d59c331c54ad826d5e566dc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Antifungal activity</topic><topic>Antifungal agents</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - pharmacology</topic><topic>Apium - chemistry</topic><topic>Benzofuran</topic><topic>Benzofurans - chemical synthesis</topic><topic>Benzofurans - chemistry</topic><topic>Benzofurans - pharmacology</topic><topic>Bioassays</topic><topic>butylphthalide derivatives</topic><topic>Derivatives</topic><topic>Drug Design</topic><topic>Fungi</topic><topic>Fungi - drug effects</topic><topic>Fungicidal activity</topic><topic>Fungicides</topic><topic>Ligusticum - chemistry</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Phytopathogenic fungi</topic><topic>Seeds - chemistry</topic><topic>Structure-Activity Relationship</topic><topic>Substitutes</topic><topic>synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Yong</creatorcontrib><creatorcontrib>Luo, Zhongfu</creatorcontrib><creatorcontrib>Luo, Bilan</creatorcontrib><creatorcontrib>Lan, Qing</creatorcontrib><creatorcontrib>Fan, Judi</creatorcontrib><creatorcontrib>Xue, Wei</creatorcontrib><creatorcontrib>Miao, Jing</creatorcontrib><creatorcontrib>Li, Yi</creatorcontrib><creatorcontrib>Tang, Lei</creatorcontrib><creatorcontrib>Fan, Lingling</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry & biodiversity</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Yong</au><au>Luo, Zhongfu</au><au>Luo, Bilan</au><au>Lan, Qing</au><au>Fan, Judi</au><au>Xue, Wei</au><au>Miao, Jing</au><au>Li, Yi</au><au>Tang, Lei</au><au>Fan, Lingling</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, Synthesis and Antifungal Activities of 6‐Substituted 3‐Butylphthalide Derivatives against Phytopathogenic Fungi</atitle><jtitle>Chemistry & biodiversity</jtitle><addtitle>Chem Biodivers</addtitle><date>2020-10</date><risdate>2020</risdate><volume>17</volume><issue>10</issue><spage>e2000435</spage><epage>n/a</epage><pages>e2000435-n/a</pages><issn>1612-1872</issn><eissn>1612-1880</eissn><abstract>In order to discover novel potential antifungal agents, a series of 6‐substituted 3‐butylphthalide derivatives were designed, synthesized and evaluated for their antifungal activities against nine phytopathogenic fungi. Preliminary bioassay tests showed that five 3‐butylphthalide derivatives exhibited more potent antifungal activities than hymexazol at the concentration of 50 μg/mL. Especially, 3‐butyl‐6‐nitro‐2‐benzofuran‐1(3H)‐one and 3‐butyl‐6‐hydroxy‐5‐nitro‐2‐benzofuran‐1(3H)‐one had significant fungicidal activity against some phytopathogenic fungi. The EC50 of 3‐butyl‐6‐nitro‐2‐benzofuran‐1(3H)‐one against FS, FO and FG were 6.6, 9.6 and 16.0 μg/mL, respectively. The EC50 of 3‐butyl‐6‐hydroxy‐5‐nitro‐2‐benzofuran‐1(3H)‐one against BC, PO, VM, SS and AS were 6.3, 5.9, 10.0, 4.5 and 8.4 μg/mL, respectively. The preliminary structure–activity relationships (SARs) of all target compounds were also investigated.</abstract><cop>Switzerland</cop><pub>Wiley Subscription Services, Inc</pub><pmid>32687253</pmid><doi>10.1002/cbdv.202000435</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-5607-3813</orcidid></addata></record> |
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| subjects | Antifungal activity Antifungal agents Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Antifungal Agents - pharmacology Apium - chemistry Benzofuran Benzofurans - chemical synthesis Benzofurans - chemistry Benzofurans - pharmacology Bioassays butylphthalide derivatives Derivatives Drug Design Fungi Fungi - drug effects Fungicidal activity Fungicides Ligusticum - chemistry Microbial Sensitivity Tests Molecular Structure Phytopathogenic fungi Seeds - chemistry Structure-Activity Relationship Substitutes synthesis |
| title | Design, Synthesis and Antifungal Activities of 6‐Substituted 3‐Butylphthalide Derivatives against Phytopathogenic Fungi |
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