Regioselective hemisynthesis and insecticidal activity of C8-hydrazones/acylhydrazones/sulfonylhydrazones coumarin-type derivatives of osthole
A series of new osthole derivatives containing hydrazone/acylhydrazone/sulfonylhydrazone skeletons at the C-8 position were regioselectively prepared. Among them, benzoylhydrazone 3b (R1 = 4-CH3Ph) showed the most potent insecticidal activity against Mythimna separata Walker. [Display omitted] Ostho...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2021-05, Vol.40, p.127962-127962, Article 127962 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Ren, Zili Lv, Min Sun, Zhiqiang Li, Tianze Zhang, Shaoyong Xu, Hui |
| description | A series of new osthole derivatives containing hydrazone/acylhydrazone/sulfonylhydrazone skeletons at the C-8 position were regioselectively prepared. Among them, benzoylhydrazone 3b (R1 = 4-CH3Ph) showed the most potent insecticidal activity against Mythimna separata Walker.
[Display omitted]
Osthole, a coumarin-type natural product, is isolated from Chinese traditional herbal medicine Cnidium monnieri. In order to improve the pesticidal activity of osthole, and high value-added application of the plant Cnidium monnieri, a series of new derivatives containing hydrazone/acylhydrazone/sulfonylhydrazone skeletons at the C-8 position of osthole were regioselectively semi-prepared. The steric structure of 3c was determined by the X-ray crystal structure. Against Mythimna separata Walker, benzoylhydrazone 3b (R1 = 4-CH3Ph) showed 1.6 folds potent insecticidal activity of the precursor osthole. Introduction of the acylhydrazones on the 3′-methyl-2′-butylenyl fragment at the C-8 position of osthole can improve the insecticidal activity. These will provide a foundation for future structural modifications of osthole as pesticidal agents. |
| doi_str_mv | 10.1016/j.bmcl.2021.127962 |
| format | Article |
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[Display omitted]
Osthole, a coumarin-type natural product, is isolated from Chinese traditional herbal medicine Cnidium monnieri. In order to improve the pesticidal activity of osthole, and high value-added application of the plant Cnidium monnieri, a series of new derivatives containing hydrazone/acylhydrazone/sulfonylhydrazone skeletons at the C-8 position of osthole were regioselectively semi-prepared. The steric structure of 3c was determined by the X-ray crystal structure. Against Mythimna separata Walker, benzoylhydrazone 3b (R1 = 4-CH3Ph) showed 1.6 folds potent insecticidal activity of the precursor osthole. Introduction of the acylhydrazones on the 3′-methyl-2′-butylenyl fragment at the C-8 position of osthole can improve the insecticidal activity. These will provide a foundation for future structural modifications of osthole as pesticidal agents.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2021.127962</identifier><identifier>PMID: 33741463</identifier><language>eng</language><publisher>OXFORD: Elsevier Ltd</publisher><subject>Chemistry ; Chemistry, Medicinal ; Chemistry, Organic ; Cnidium monnieri ; Coumarin-type ; Insecticidal activity ; Life Sciences & Biomedicine ; Osthole ; Pharmacology & Pharmacy ; Physical Sciences ; Plant-derived product ; Science & Technology</subject><ispartof>Bioorganic & medicinal chemistry letters, 2021-05, Vol.40, p.127962-127962, Article 127962</ispartof><rights>2021 Elsevier Ltd</rights><rights>Copyright © 2021 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>true</woscitedreferencessubscribed><woscitedreferencescount>15</woscitedreferencescount><woscitedreferencesoriginalsourcerecordid>wos000663617900003</woscitedreferencesoriginalsourcerecordid><citedby>FETCH-LOGICAL-c356t-5dbdaea746fe5e72a96abcefcfe9efb73bf23f8616608a72805229eeb314cfe3</citedby><cites>FETCH-LOGICAL-c356t-5dbdaea746fe5e72a96abcefcfe9efb73bf23f8616608a72805229eeb314cfe3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2021.127962$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27928,27929,45999</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33741463$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ren, Zili</creatorcontrib><creatorcontrib>Lv, Min</creatorcontrib><creatorcontrib>Sun, Zhiqiang</creatorcontrib><creatorcontrib>Li, Tianze</creatorcontrib><creatorcontrib>Zhang, Shaoyong</creatorcontrib><creatorcontrib>Xu, Hui</creatorcontrib><title>Regioselective hemisynthesis and insecticidal activity of C8-hydrazones/acylhydrazones/sulfonylhydrazones coumarin-type derivatives of osthole</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>BIOORG MED CHEM LETT</addtitle><addtitle>Bioorg Med Chem Lett</addtitle><description>A series of new osthole derivatives containing hydrazone/acylhydrazone/sulfonylhydrazone skeletons at the C-8 position were regioselectively prepared. Among them, benzoylhydrazone 3b (R1 = 4-CH3Ph) showed the most potent insecticidal activity against Mythimna separata Walker.
[Display omitted]
Osthole, a coumarin-type natural product, is isolated from Chinese traditional herbal medicine Cnidium monnieri. In order to improve the pesticidal activity of osthole, and high value-added application of the plant Cnidium monnieri, a series of new derivatives containing hydrazone/acylhydrazone/sulfonylhydrazone skeletons at the C-8 position of osthole were regioselectively semi-prepared. The steric structure of 3c was determined by the X-ray crystal structure. Against Mythimna separata Walker, benzoylhydrazone 3b (R1 = 4-CH3Ph) showed 1.6 folds potent insecticidal activity of the precursor osthole. Introduction of the acylhydrazones on the 3′-methyl-2′-butylenyl fragment at the C-8 position of osthole can improve the insecticidal activity. These will provide a foundation for future structural modifications of osthole as pesticidal agents.</description><subject>Chemistry</subject><subject>Chemistry, Medicinal</subject><subject>Chemistry, Organic</subject><subject>Cnidium monnieri</subject><subject>Coumarin-type</subject><subject>Insecticidal activity</subject><subject>Life Sciences & Biomedicine</subject><subject>Osthole</subject><subject>Pharmacology & Pharmacy</subject><subject>Physical Sciences</subject><subject>Plant-derived product</subject><subject>Science & Technology</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>HGBXW</sourceid><recordid>eNqNkctq3DAYhUVpaKZpX6CL4mWheKKbZRu6KaY3CARCFtkJWf7V0eCRppI8xX2IPnNlPA1Zla50-84vzjkIvSF4SzAR1_ttf9DjlmJKtoTWraDP0IZwwUvGcfUcbXArcNm0_OESvYxxjzHhmPMX6JKxmmeQbdDvO_hufYQRdLInKHZwsHF2aQfRxkK5obAuLm_aDmos1ELZNBfeFF1T7uYhqF_eQbxWeh6fHOM0Gu-eXhXaTwcVrCvTfIRigGBPavkzLsN8TDs_wit0YdQY4fV5vUL3nz_dd1_Lm9sv37qPN6VmlUhlNfSDAlVzYaCCmqpWqF6D0QZaMH3NekOZaQQRAjeqpg2uKG0BekZ4ZtgVereOPQb_Y4KYZHatYRyVAz9FSSvMOG8qKjJKV1QHH2MAI4_BZh-zJFguNci9XGqQSw1yrSGL3p7nT_0BhkfJ39wz0KzAT-i9idqC0_CIYYyFYILUbd5h1tmUg_Ku85NLWfr-_6WZ_rDSkNM8WQjyrBhsyLXKwdt_GfkDAk_AKw</recordid><startdate>20210515</startdate><enddate>20210515</enddate><creator>Ren, Zili</creator><creator>Lv, Min</creator><creator>Sun, Zhiqiang</creator><creator>Li, Tianze</creator><creator>Zhang, Shaoyong</creator><creator>Xu, Hui</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>1KM</scope><scope>BLEPL</scope><scope>DTL</scope><scope>HGBXW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20210515</creationdate><title>Regioselective hemisynthesis and insecticidal activity of C8-hydrazones/acylhydrazones/sulfonylhydrazones coumarin-type derivatives of osthole</title><author>Ren, Zili ; Lv, Min ; Sun, Zhiqiang ; Li, Tianze ; Zhang, Shaoyong ; Xu, Hui</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-5dbdaea746fe5e72a96abcefcfe9efb73bf23f8616608a72805229eeb314cfe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Chemistry</topic><topic>Chemistry, Medicinal</topic><topic>Chemistry, Organic</topic><topic>Cnidium monnieri</topic><topic>Coumarin-type</topic><topic>Insecticidal activity</topic><topic>Life Sciences & Biomedicine</topic><topic>Osthole</topic><topic>Pharmacology & Pharmacy</topic><topic>Physical Sciences</topic><topic>Plant-derived product</topic><topic>Science & Technology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ren, Zili</creatorcontrib><creatorcontrib>Lv, Min</creatorcontrib><creatorcontrib>Sun, Zhiqiang</creatorcontrib><creatorcontrib>Li, Tianze</creatorcontrib><creatorcontrib>Zhang, Shaoyong</creatorcontrib><creatorcontrib>Xu, Hui</creatorcontrib><collection>Index Chemicus</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>Web of Science - Science Citation Index Expanded - 2021</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ren, Zili</au><au>Lv, Min</au><au>Sun, Zhiqiang</au><au>Li, Tianze</au><au>Zhang, Shaoyong</au><au>Xu, Hui</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regioselective hemisynthesis and insecticidal activity of C8-hydrazones/acylhydrazones/sulfonylhydrazones coumarin-type derivatives of osthole</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><stitle>BIOORG MED CHEM LETT</stitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2021-05-15</date><risdate>2021</risdate><volume>40</volume><spage>127962</spage><epage>127962</epage><pages>127962-127962</pages><artnum>127962</artnum><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A series of new osthole derivatives containing hydrazone/acylhydrazone/sulfonylhydrazone skeletons at the C-8 position were regioselectively prepared. Among them, benzoylhydrazone 3b (R1 = 4-CH3Ph) showed the most potent insecticidal activity against Mythimna separata Walker.
[Display omitted]
Osthole, a coumarin-type natural product, is isolated from Chinese traditional herbal medicine Cnidium monnieri. In order to improve the pesticidal activity of osthole, and high value-added application of the plant Cnidium monnieri, a series of new derivatives containing hydrazone/acylhydrazone/sulfonylhydrazone skeletons at the C-8 position of osthole were regioselectively semi-prepared. The steric structure of 3c was determined by the X-ray crystal structure. Against Mythimna separata Walker, benzoylhydrazone 3b (R1 = 4-CH3Ph) showed 1.6 folds potent insecticidal activity of the precursor osthole. Introduction of the acylhydrazones on the 3′-methyl-2′-butylenyl fragment at the C-8 position of osthole can improve the insecticidal activity. These will provide a foundation for future structural modifications of osthole as pesticidal agents.</abstract><cop>OXFORD</cop><pub>Elsevier Ltd</pub><pmid>33741463</pmid><doi>10.1016/j.bmcl.2021.127962</doi><tpages>5</tpages></addata></record> |
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| subjects | Chemistry Chemistry, Medicinal Chemistry, Organic Cnidium monnieri Coumarin-type Insecticidal activity Life Sciences & Biomedicine Osthole Pharmacology & Pharmacy Physical Sciences Plant-derived product Science & Technology |
| title | Regioselective hemisynthesis and insecticidal activity of C8-hydrazones/acylhydrazones/sulfonylhydrazones coumarin-type derivatives of osthole |
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