Facile Synthesis of Novel Vanillin Derivatives Incorporating a Bis(2-hydroxyethyl)dithhioacetal Moiety as Antiviral Agents
A series of vanillin derivatives incorporating a bis(2-hydroxyethyl)dithioacetal moiety was designed and synthesized via a facile method. A plausible reaction pathway was proposed and verified by computational studies. Bioassay results demonstrated that target compounds possessed good to excellent...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2017-06, Vol.65 (23), p.4582-4588 |
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| container_end_page | 4588 |
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| container_issue | 23 |
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| container_title | Journal of agricultural and food chemistry |
| container_volume | 65 |
| creator | Zhang, Jian Zhao, Lei Zhu, Chun Wu, Zengxue Zhang, Guoping Gan, Xiuhai Liu, Dengyue Pan, Jianke Hu, Deyu Song, Baoan |
| description | A series of vanillin derivatives incorporating a bis(2-hydroxyethyl)dithioacetal moiety was designed and synthesized via a facile method. A plausible reaction pathway was proposed and verified by computational studies. Bioassay results demonstrated that target compounds possessed good to excellent activities against potato virus Y (PVY) and cucumber mosaic virus (CMV), of which, compound 6f incorporating a bis(2-hydroxyethyl)dithioacetal moiety, exhibited the best curative and protection activities against PVY and CMV in vivo, with 50% effective concentration values of 217.6, 205.7 μg/mL and 206.3, 186.2 μg/mL, respectively, better than those of ribavirin (848.0, 808.1 μg/mL and 858.2, 766.5 μg/mL, respectively), dufulin (462.6, 454.8 μg/mL and 471.2, 465.4 μg/mL, respectively), and ningnanmycin (440.5, 425.3 μg/mL and 426.1, 405.3 μg/mL, respectively). Current studies provide support for the application of vanillin derivatives incorporating bis(2-hydroxyethyl)dithioacetal as new antiviral agents. |
| doi_str_mv | 10.1021/acs.jafc.7b01035 |
| format | Article |
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A plausible reaction pathway was proposed and verified by computational studies. Bioassay results demonstrated that target compounds possessed good to excellent activities against potato virus Y (PVY) and cucumber mosaic virus (CMV), of which, compound 6f incorporating a bis(2-hydroxyethyl)dithioacetal moiety, exhibited the best curative and protection activities against PVY and CMV in vivo, with 50% effective concentration values of 217.6, 205.7 μg/mL and 206.3, 186.2 μg/mL, respectively, better than those of ribavirin (848.0, 808.1 μg/mL and 858.2, 766.5 μg/mL, respectively), dufulin (462.6, 454.8 μg/mL and 471.2, 465.4 μg/mL, respectively), and ningnanmycin (440.5, 425.3 μg/mL and 426.1, 405.3 μg/mL, respectively). Current studies provide support for the application of vanillin derivatives incorporating bis(2-hydroxyethyl)dithioacetal as new antiviral agents.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/acs.jafc.7b01035</identifier><identifier>PMID: 28545296</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Benzaldehydes - chemistry ; Benzaldehydes - pharmacology ; Cucumovirus - drug effects ; Drug Design ; Structure-Activity Relationship ; Tobacco Mosaic Virus - drug effects</subject><ispartof>Journal of agricultural and food chemistry, 2017-06, Vol.65 (23), p.4582-4588</ispartof><rights>Copyright © 2017 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a336t-90433602d5be35bc668d7b7628857aa0a366845677ccfac382e853c90fc2ab3f3</citedby><cites>FETCH-LOGICAL-a336t-90433602d5be35bc668d7b7628857aa0a366845677ccfac382e853c90fc2ab3f3</cites><orcidid>0000-0002-4237-6167</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.jafc.7b01035$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jafc.7b01035$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28545296$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Jian</creatorcontrib><creatorcontrib>Zhao, Lei</creatorcontrib><creatorcontrib>Zhu, Chun</creatorcontrib><creatorcontrib>Wu, Zengxue</creatorcontrib><creatorcontrib>Zhang, Guoping</creatorcontrib><creatorcontrib>Gan, Xiuhai</creatorcontrib><creatorcontrib>Liu, Dengyue</creatorcontrib><creatorcontrib>Pan, Jianke</creatorcontrib><creatorcontrib>Hu, Deyu</creatorcontrib><creatorcontrib>Song, Baoan</creatorcontrib><title>Facile Synthesis of Novel Vanillin Derivatives Incorporating a Bis(2-hydroxyethyl)dithhioacetal Moiety as Antiviral Agents</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>A series of vanillin derivatives incorporating a bis(2-hydroxyethyl)dithioacetal moiety was designed and synthesized via a facile method. A plausible reaction pathway was proposed and verified by computational studies. Bioassay results demonstrated that target compounds possessed good to excellent activities against potato virus Y (PVY) and cucumber mosaic virus (CMV), of which, compound 6f incorporating a bis(2-hydroxyethyl)dithioacetal moiety, exhibited the best curative and protection activities against PVY and CMV in vivo, with 50% effective concentration values of 217.6, 205.7 μg/mL and 206.3, 186.2 μg/mL, respectively, better than those of ribavirin (848.0, 808.1 μg/mL and 858.2, 766.5 μg/mL, respectively), dufulin (462.6, 454.8 μg/mL and 471.2, 465.4 μg/mL, respectively), and ningnanmycin (440.5, 425.3 μg/mL and 426.1, 405.3 μg/mL, respectively). Current studies provide support for the application of vanillin derivatives incorporating bis(2-hydroxyethyl)dithioacetal as new antiviral agents.</description><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Benzaldehydes - chemistry</subject><subject>Benzaldehydes - pharmacology</subject><subject>Cucumovirus - drug effects</subject><subject>Drug Design</subject><subject>Structure-Activity Relationship</subject><subject>Tobacco Mosaic Virus - drug effects</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kE1vEzEQhi0EoqFw54R8LBIbxna8uzmGQqFSgQMf19Wsd7bryrGD7UQsvx6XBG6cRjN63leah7HnApYCpHiNJi3vcDTLpgcBSj9gC6ElVFqI9iFbQGGqVtfijD1J6Q4AWt3AY3YmW73Scl0v2K8rNNYR_zL7PFGyiYeRfwoHcvw7euuc9fwtRXvAbA-U-LU3Ie5CLKu_5cjf2HQhq2keYvg5U55m93KweZpsQEMZHf8YLOWZY-IbXypsLLfNLfmcnrJHI7pEz07znH27evf18kN18_n99eXmpkKl6lytYVUmyEH3pHRv6rodmr6pZVueQQRU5bLSddMYM6JRraRWK7OG0Ujs1ajO2cWxdxfDjz2l3G1tMuQcegr71Ik1KFFLKVcFhSNqYkgp0tjtot1inDsB3b3xrhjv7o13J-Ml8uLUvu-3NPwL_FVcgFdH4E807KMvz_6_7zf0zI4G</recordid><startdate>20170614</startdate><enddate>20170614</enddate><creator>Zhang, Jian</creator><creator>Zhao, Lei</creator><creator>Zhu, Chun</creator><creator>Wu, Zengxue</creator><creator>Zhang, Guoping</creator><creator>Gan, Xiuhai</creator><creator>Liu, Dengyue</creator><creator>Pan, Jianke</creator><creator>Hu, Deyu</creator><creator>Song, Baoan</creator><general>American Chemical Society</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>7X8</scope><orcidid>https://orcid.org/0000-0002-4237-6167</orcidid></search><sort><creationdate>20170614</creationdate><title>Facile Synthesis of Novel Vanillin Derivatives Incorporating a Bis(2-hydroxyethyl)dithhioacetal Moiety as Antiviral Agents</title><author>Zhang, Jian ; Zhao, Lei ; Zhu, Chun ; Wu, Zengxue ; Zhang, Guoping ; Gan, Xiuhai ; Liu, Dengyue ; Pan, Jianke ; Hu, Deyu ; Song, Baoan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a336t-90433602d5be35bc668d7b7628857aa0a366845677ccfac382e853c90fc2ab3f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - pharmacology</topic><topic>Benzaldehydes - chemistry</topic><topic>Benzaldehydes - pharmacology</topic><topic>Cucumovirus - drug effects</topic><topic>Drug Design</topic><topic>Structure-Activity Relationship</topic><topic>Tobacco Mosaic Virus - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Jian</creatorcontrib><creatorcontrib>Zhao, Lei</creatorcontrib><creatorcontrib>Zhu, Chun</creatorcontrib><creatorcontrib>Wu, Zengxue</creatorcontrib><creatorcontrib>Zhang, Guoping</creatorcontrib><creatorcontrib>Gan, Xiuhai</creatorcontrib><creatorcontrib>Liu, Dengyue</creatorcontrib><creatorcontrib>Pan, Jianke</creatorcontrib><creatorcontrib>Hu, Deyu</creatorcontrib><creatorcontrib>Song, Baoan</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Jian</au><au>Zhao, Lei</au><au>Zhu, Chun</au><au>Wu, Zengxue</au><au>Zhang, Guoping</au><au>Gan, Xiuhai</au><au>Liu, Dengyue</au><au>Pan, Jianke</au><au>Hu, Deyu</au><au>Song, Baoan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Facile Synthesis of Novel Vanillin Derivatives Incorporating a Bis(2-hydroxyethyl)dithhioacetal Moiety as Antiviral Agents</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2017-06-14</date><risdate>2017</risdate><volume>65</volume><issue>23</issue><spage>4582</spage><epage>4588</epage><pages>4582-4588</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><abstract>A series of vanillin derivatives incorporating a bis(2-hydroxyethyl)dithioacetal moiety was designed and synthesized via a facile method. A plausible reaction pathway was proposed and verified by computational studies. Bioassay results demonstrated that target compounds possessed good to excellent activities against potato virus Y (PVY) and cucumber mosaic virus (CMV), of which, compound 6f incorporating a bis(2-hydroxyethyl)dithioacetal moiety, exhibited the best curative and protection activities against PVY and CMV in vivo, with 50% effective concentration values of 217.6, 205.7 μg/mL and 206.3, 186.2 μg/mL, respectively, better than those of ribavirin (848.0, 808.1 μg/mL and 858.2, 766.5 μg/mL, respectively), dufulin (462.6, 454.8 μg/mL and 471.2, 465.4 μg/mL, respectively), and ningnanmycin (440.5, 425.3 μg/mL and 426.1, 405.3 μg/mL, respectively). Current studies provide support for the application of vanillin derivatives incorporating bis(2-hydroxyethyl)dithioacetal as new antiviral agents.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>28545296</pmid><doi>10.1021/acs.jafc.7b01035</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-4237-6167</orcidid></addata></record> |
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| subjects | Antiviral Agents - chemistry Antiviral Agents - pharmacology Benzaldehydes - chemistry Benzaldehydes - pharmacology Cucumovirus - drug effects Drug Design Structure-Activity Relationship Tobacco Mosaic Virus - drug effects |
| title | Facile Synthesis of Novel Vanillin Derivatives Incorporating a Bis(2-hydroxyethyl)dithhioacetal Moiety as Antiviral Agents |
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