新型昆虫拒食和杀蜱诺卡酮衍生物。
Novel Insect Antifeedant and Ixodicidal Nootkatone Derivatives.
机构信息
Department of Organic Chemistry, Institute of Biotechnology, University of Granada, 18071 Granada, Spain.
Faculty of Veterinary, Complutense University of Madrid (UCM), 28040 Madrid, Spain.
出版信息
Biomolecules. 2019 Nov 16;9(11):742. doi: 10.3390/biom9110742.
Naturally occurring nootkatone, with reported insecticidal and acaricidal properties, has been used as a lead to generate molecular diversity and, consequently, new insect antifeedant and ixodicidal compounds. A total of 22 derivatives were generated by subjecting this molecule to several reactions including dehydrogenation with the iodine/DMSO system, oxidation with SeO, epoxidation with CPBA, oxidation or carbon homologations of the α-carbonyl position with TMSOTf (trimethylsilyl trifluoromethanesulfonate) followed by Rubottom and Dess Martin periodane oxidations, condensation with formaldehyde using Yb(OTf) as catalyst and dehydroxilation using the Grieco protocol. The insect antifeedant (against and ) and ixodicidal (against the tick ) activities of these compounds were tested. Compound was the most active substance against and , and twice more efficient than nootkatone in the antitick test.
天然存在的诺卡酮具有杀虫和杀螨特性，已被用作产生分子多样性的先导化合物，从而生成新的昆虫拒食剂和杀蜱化合物。通过对该分子进行几种反应，包括用碘/DMSO 体系脱氢、用 SeO 氧化、用 CPBA 环氧化、用 TMSOTf（三甲基硅基三氟甲烷磺酸酯）对α-羰基位置进行氧化或同碳加成，然后进行 Rubottom 和 Dess Martin 过碘烷氧化、用 Yb(OTf) 作为催化剂与甲醛缩合以及用 Grieco 方案进行脱羟，共生成了 22 种衍生物。对这些化合物的昆虫拒食（针对 和 ）和杀蜱（针对蜱虫）活性进行了测试。化合物 对 和 是最有效的物质，在抗蜱试验中的效率比诺卡酮高两倍。
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