Syntheses, antiviral activities and induced resistance mechanisms of novel quinazoline derivatives containing a dithioacetal moiety
[Display omitted] •Novel quinazoline derivatives containing dithioacetal moiety were designed and synthesized.•Compound 4b exhibited excellent activity against cucumber mosaic virus and potato virus Y.•Compound 4b can induce resistance of tobacco. A series of novel quinazoline derivatives containing...
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| Veröffentlicht in: | Bioorganic chemistry 2018-10, Vol.80, p.433-443 |
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| container_title | Bioorganic chemistry |
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| creator | Xie, Dandan Shi, Jing Zhang, Awei Lei, Zhiwei Zu, Guangcheng Fu, Yun Gan, Xiuhai Yin, Limin Song, Baoan Hu, Deyu |
| description | [Display omitted]
•Novel quinazoline derivatives containing dithioacetal moiety were designed and synthesized.•Compound 4b exhibited excellent activity against cucumber mosaic virus and potato virus Y.•Compound 4b can induce resistance of tobacco.
A series of novel quinazoline derivatives containing a dithioacetal moiety were designed and synthesized, and their structures were characterized by 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, and high-resolution mass spectrometry. Bioassay results indicated that compound 4b exhibited remarkable protective activity against cucumber mosaic virus (CMV, EC50 = 248.6 μg/mL) and curative activity against potato virus Y (EC50 = 350.5 μg/mL), which were better than those of ningnanmycin (357.7 μg/mL and 493.7 μg/mL, respectively). Moreover, compound 4b could increase the chlorophyll content in plants, improve photosynthesis, and effectively induce tobacco anti-CMV activity. |
| doi_str_mv | 10.1016/j.bioorg.2018.06.026 |
| format | Article |
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•Novel quinazoline derivatives containing dithioacetal moiety were designed and synthesized.•Compound 4b exhibited excellent activity against cucumber mosaic virus and potato virus Y.•Compound 4b can induce resistance of tobacco.
A series of novel quinazoline derivatives containing a dithioacetal moiety were designed and synthesized, and their structures were characterized by 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, and high-resolution mass spectrometry. Bioassay results indicated that compound 4b exhibited remarkable protective activity against cucumber mosaic virus (CMV, EC50 = 248.6 μg/mL) and curative activity against potato virus Y (EC50 = 350.5 μg/mL), which were better than those of ningnanmycin (357.7 μg/mL and 493.7 μg/mL, respectively). Moreover, compound 4b could increase the chlorophyll content in plants, improve photosynthesis, and effectively induce tobacco anti-CMV activity.</description><identifier>ISSN: 0045-2068</identifier><identifier>EISSN: 1090-2120</identifier><identifier>DOI: 10.1016/j.bioorg.2018.06.026</identifier><identifier>PMID: 29986188</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Acetals - chemical synthesis ; Acetals - chemistry ; Acetals - pharmacology ; Antiviral activity ; Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Cucumber mosaic virus ; Cucumovirus - drug effects ; Disease Resistance - drug effects ; Dithioacetal moiety ; Drug Design ; Induced resistance mechanism ; Nicotiana - virology ; Plant Diseases - prevention & control ; Plant Diseases - virology ; Potyvirus - drug effects ; Quinazoline derivatives ; Quinazolines - chemical synthesis ; Quinazolines - chemistry ; Quinazolines - pharmacology</subject><ispartof>Bioorganic chemistry, 2018-10, Vol.80, p.433-443</ispartof><rights>2018 Elsevier Inc.</rights><rights>Copyright © 2018 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c362t-85c7258f170ddca6dd86f556f0214595e83dc80884c14ad43a2644509a74d4223</citedby><cites>FETCH-LOGICAL-c362t-85c7258f170ddca6dd86f556f0214595e83dc80884c14ad43a2644509a74d4223</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bioorg.2018.06.026$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27923,27924,45994</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29986188$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Xie, Dandan</creatorcontrib><creatorcontrib>Shi, Jing</creatorcontrib><creatorcontrib>Zhang, Awei</creatorcontrib><creatorcontrib>Lei, Zhiwei</creatorcontrib><creatorcontrib>Zu, Guangcheng</creatorcontrib><creatorcontrib>Fu, Yun</creatorcontrib><creatorcontrib>Gan, Xiuhai</creatorcontrib><creatorcontrib>Yin, Limin</creatorcontrib><creatorcontrib>Song, Baoan</creatorcontrib><creatorcontrib>Hu, Deyu</creatorcontrib><title>Syntheses, antiviral activities and induced resistance mechanisms of novel quinazoline derivatives containing a dithioacetal moiety</title><title>Bioorganic chemistry</title><addtitle>Bioorg Chem</addtitle><description>[Display omitted]
•Novel quinazoline derivatives containing dithioacetal moiety were designed and synthesized.•Compound 4b exhibited excellent activity against cucumber mosaic virus and potato virus Y.•Compound 4b can induce resistance of tobacco.
A series of novel quinazoline derivatives containing a dithioacetal moiety were designed and synthesized, and their structures were characterized by 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, and high-resolution mass spectrometry. Bioassay results indicated that compound 4b exhibited remarkable protective activity against cucumber mosaic virus (CMV, EC50 = 248.6 μg/mL) and curative activity against potato virus Y (EC50 = 350.5 μg/mL), which were better than those of ningnanmycin (357.7 μg/mL and 493.7 μg/mL, respectively). Moreover, compound 4b could increase the chlorophyll content in plants, improve photosynthesis, and effectively induce tobacco anti-CMV activity.</description><subject>Acetals - chemical synthesis</subject><subject>Acetals - chemistry</subject><subject>Acetals - pharmacology</subject><subject>Antiviral activity</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Cucumber mosaic virus</subject><subject>Cucumovirus - drug effects</subject><subject>Disease Resistance - drug effects</subject><subject>Dithioacetal moiety</subject><subject>Drug Design</subject><subject>Induced resistance mechanism</subject><subject>Nicotiana - virology</subject><subject>Plant Diseases - prevention & control</subject><subject>Plant Diseases - virology</subject><subject>Potyvirus - drug effects</subject><subject>Quinazoline derivatives</subject><subject>Quinazolines - chemical synthesis</subject><subject>Quinazolines - chemistry</subject><subject>Quinazolines - pharmacology</subject><issn>0045-2068</issn><issn>1090-2120</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1r3DAQhkVpabZp_0EpOvZQO5Isy_KlUEL6AYEe0p6FIo2zs9hSIskLm2v_eLRs2mNPMwzvB_MQ8p6zljOuLnbtLcaY7lrBuG6ZaplQL8iGs5E1ggv2kmwYk30jmNJn5E3OO8Y4l4N6Tc7EOGrFtd6QPzeHULaQIX-iNhTcY7Izte64FYRcj55i8KsDTxNkzMUGB3QBt7UB85JpnGiIe5jpw4rBPsYZA1APCfe2ptQIF0OxGDDcUUs9li1G66DUniUilMNb8mqyc4Z3z_Oc_P569evye3P989uPyy_XjeuUKI3u3SB6PfGBee-s8l6rqe_VxASX_diD7rzTTGvpuLRedlYoKXs22kF6KUR3Tj6ecu9TfFghF7NgdjDPNkBcs6mkBj12UssqlSepSzHnBJO5T7jYdDCcmSN-szMn_OaI3zBlKv5q-_DcsN4u4P-Z_vKugs8nAdQ_9wjJZIdQgXpM4IrxEf_f8AQz_5sn</recordid><startdate>201810</startdate><enddate>201810</enddate><creator>Xie, Dandan</creator><creator>Shi, Jing</creator><creator>Zhang, Awei</creator><creator>Lei, Zhiwei</creator><creator>Zu, Guangcheng</creator><creator>Fu, Yun</creator><creator>Gan, Xiuhai</creator><creator>Yin, Limin</creator><creator>Song, Baoan</creator><creator>Hu, Deyu</creator><general>Elsevier 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>7X8</scope></search><sort><creationdate>201810</creationdate><title>Syntheses, antiviral activities and induced resistance mechanisms of novel quinazoline derivatives containing a dithioacetal moiety</title><author>Xie, Dandan ; Shi, Jing ; Zhang, Awei ; Lei, Zhiwei ; Zu, Guangcheng ; Fu, Yun ; Gan, Xiuhai ; Yin, Limin ; Song, Baoan ; Hu, Deyu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c362t-85c7258f170ddca6dd86f556f0214595e83dc80884c14ad43a2644509a74d4223</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Acetals - chemical synthesis</topic><topic>Acetals - chemistry</topic><topic>Acetals - pharmacology</topic><topic>Antiviral activity</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - pharmacology</topic><topic>Cucumber mosaic virus</topic><topic>Cucumovirus - drug effects</topic><topic>Disease Resistance - drug effects</topic><topic>Dithioacetal moiety</topic><topic>Drug Design</topic><topic>Induced resistance mechanism</topic><topic>Nicotiana - virology</topic><topic>Plant Diseases - prevention & control</topic><topic>Plant Diseases - virology</topic><topic>Potyvirus - drug effects</topic><topic>Quinazoline derivatives</topic><topic>Quinazolines - chemical synthesis</topic><topic>Quinazolines - chemistry</topic><topic>Quinazolines - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xie, Dandan</creatorcontrib><creatorcontrib>Shi, Jing</creatorcontrib><creatorcontrib>Zhang, Awei</creatorcontrib><creatorcontrib>Lei, Zhiwei</creatorcontrib><creatorcontrib>Zu, Guangcheng</creatorcontrib><creatorcontrib>Fu, Yun</creatorcontrib><creatorcontrib>Gan, Xiuhai</creatorcontrib><creatorcontrib>Yin, Limin</creatorcontrib><creatorcontrib>Song, Baoan</creatorcontrib><creatorcontrib>Hu, Deyu</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>Bioorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xie, Dandan</au><au>Shi, Jing</au><au>Zhang, Awei</au><au>Lei, Zhiwei</au><au>Zu, Guangcheng</au><au>Fu, Yun</au><au>Gan, Xiuhai</au><au>Yin, Limin</au><au>Song, Baoan</au><au>Hu, Deyu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Syntheses, antiviral activities and induced resistance mechanisms of novel quinazoline derivatives containing a dithioacetal moiety</atitle><jtitle>Bioorganic chemistry</jtitle><addtitle>Bioorg Chem</addtitle><date>2018-10</date><risdate>2018</risdate><volume>80</volume><spage>433</spage><epage>443</epage><pages>433-443</pages><issn>0045-2068</issn><eissn>1090-2120</eissn><abstract>[Display omitted]
•Novel quinazoline derivatives containing dithioacetal moiety were designed and synthesized.•Compound 4b exhibited excellent activity against cucumber mosaic virus and potato virus Y.•Compound 4b can induce resistance of tobacco.
A series of novel quinazoline derivatives containing a dithioacetal moiety were designed and synthesized, and their structures were characterized by 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, and high-resolution mass spectrometry. Bioassay results indicated that compound 4b exhibited remarkable protective activity against cucumber mosaic virus (CMV, EC50 = 248.6 μg/mL) and curative activity against potato virus Y (EC50 = 350.5 μg/mL), which were better than those of ningnanmycin (357.7 μg/mL and 493.7 μg/mL, respectively). Moreover, compound 4b could increase the chlorophyll content in plants, improve photosynthesis, and effectively induce tobacco anti-CMV activity.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>29986188</pmid><doi>10.1016/j.bioorg.2018.06.026</doi><tpages>11</tpages></addata></record> |
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| subjects | Acetals - chemical synthesis Acetals - chemistry Acetals - pharmacology Antiviral activity Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Cucumber mosaic virus Cucumovirus - drug effects Disease Resistance - drug effects Dithioacetal moiety Drug Design Induced resistance mechanism Nicotiana - virology Plant Diseases - prevention & control Plant Diseases - virology Potyvirus - drug effects Quinazoline derivatives Quinazolines - chemical synthesis Quinazolines - chemistry Quinazolines - pharmacology |
| title | Syntheses, antiviral activities and induced resistance mechanisms of novel quinazoline derivatives containing a dithioacetal moiety |
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