Furan-site transformations of obacunone as potent insecticidal agents
Furan ring is a key pharmacophore for insecticidal activity of limoninoids. To develop natural-product-based insecticidal agents, a series of furan-site transformations (2, 3 and 3a–j) of obacunone were synthesized by selective bromination and following coupling reactions without altering other func...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2018-12-01
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| Series: | Heliyon |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844018358845 |
| _version_ | 1811341950116167680 |
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| author | Ping Xiang Qing-Hao Cao Qing-Miao Dong Xiao-Jun Yang Jiang-Jiang Tang Hongjin Bai |
| author_facet | Ping Xiang Qing-Hao Cao Qing-Miao Dong Xiao-Jun Yang Jiang-Jiang Tang Hongjin Bai |
| author_sort | Ping Xiang |
| collection | DOAJ |
| description | Furan ring is a key pharmacophore for insecticidal activity of limoninoids. To develop natural-product-based insecticidal agents, a series of furan-site transformations (2, 3 and 3a–j) of obacunone were synthesized by selective bromination and following coupling reactions without altering other functional groups. Bioassays indicated that derivatives 3e, 3f and 3j displayed more potent insecticidal activity than obacunone and toosendanin against the instar larvae of Mythimna separate Walker. Besides, their structure–activity relationships were discussed. |
| first_indexed | 2024-04-13T19:03:09Z |
| format | Article |
| id | doaj.art-f4f7c29b99d047049c97715641e18cc8 |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-04-13T19:03:09Z |
| publishDate | 2018-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-f4f7c29b99d047049c97715641e18cc82022-12-22T02:34:03ZengElsevierHeliyon2405-84402018-12-01412e01064Furan-site transformations of obacunone as potent insecticidal agentsPing Xiang0Qing-Hao Cao1Qing-Miao Dong2Xiao-Jun Yang3Jiang-Jiang Tang4Hongjin Bai5College of Plant Protection, Northwest A&F University, Yangling, 712100, PR China; Xinjiang Production & Construction Corps Key Laboratory of Protection and Utilization of Biological Resources in Tarim Basin, Tarim University, Alar 843300, PR ChinaShaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, 712100, Shaanxi, PR ChinaShaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, 712100, Shaanxi, PR ChinaSchool of Chemistry & Chemical Engineering, Yanan University, Yanan 716000, Shaanxi, PR ChinaXinjiang Production & Construction Corps Key Laboratory of Protection and Utilization of Biological Resources in Tarim Basin, Tarim University, Alar 843300, PR China; Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, 712100, Shaanxi, PR China; Corresponding author.Xinjiang Production & Construction Corps Key Laboratory of Protection and Utilization of Biological Resources in Tarim Basin, Tarim University, Alar 843300, PR China; Engineering Laboratory of Chemical Resources Utilization in South Xinjiang of Xinjiang Production & Construction Corps, Tarim University, Alar 843300, PR ChinaFuran ring is a key pharmacophore for insecticidal activity of limoninoids. To develop natural-product-based insecticidal agents, a series of furan-site transformations (2, 3 and 3a–j) of obacunone were synthesized by selective bromination and following coupling reactions without altering other functional groups. Bioassays indicated that derivatives 3e, 3f and 3j displayed more potent insecticidal activity than obacunone and toosendanin against the instar larvae of Mythimna separate Walker. Besides, their structure–activity relationships were discussed.http://www.sciencedirect.com/science/article/pii/S2405844018358845Natural product chemistry |
| spellingShingle | Ping Xiang Qing-Hao Cao Qing-Miao Dong Xiao-Jun Yang Jiang-Jiang Tang Hongjin Bai Furan-site transformations of obacunone as potent insecticidal agents Heliyon Natural product chemistry |
| title | Furan-site transformations of obacunone as potent insecticidal agents |
| title_full | Furan-site transformations of obacunone as potent insecticidal agents |
| title_fullStr | Furan-site transformations of obacunone as potent insecticidal agents |
| title_full_unstemmed | Furan-site transformations of obacunone as potent insecticidal agents |
| title_short | Furan-site transformations of obacunone as potent insecticidal agents |
| title_sort | furan site transformations of obacunone as potent insecticidal agents |
| topic | Natural product chemistry |
| url | http://www.sciencedirect.com/science/article/pii/S2405844018358845 |
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