Nootkatone thioether derivative containing 1,3,4-oxadiazole ring as well as preparation method and application of notkatone thioether derivative

Abstract

The invention discloses a series of novel nookatone thioether derivatives each containing a 1,3,4-oxadiazole ring, and a preparation method and application of the novel nookatone thioether derivatives. According to the series of compounds, nootkatone serves as a raw material, chlorine atoms are introduced to the allyl position of nootkatone to synthesize 13-chloro nootkatone, the 13-chloro nootkatone and 5-aryl-2-sulfydryl-1,3,4-oxadiazole are subjected to a substitution reaction to generate a series of novel nootkatone derivatives, and the structural general formula of the nootkatone derivatives is shown in the formula (I). According to the nootkatone thioether derivatives, the 1,3,4-oxadiazole group has various biological activities, especially in the aspect of insecticidal activity, after the nootkatone thioether derivative is combined with nootkatone, the derivative has good insecticidal activity, and the nootkatone thioether derivative is expected to be used for preparing a novel natural product insecticide; and the compound is simple in preparation process, low in cost and relatively non-toxic to non-standard target biological fish and shrimp seeds. In the formula, R is selected from non-substituted or substituted phenyl or pyridyl, and the substituted phenyl is phenyl substituted by halogen, C1-C4 alkyl, C1-C4 alkoxy, nitro or cyano.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and relates to nokatone derivatives, in particular to a series of nokatone sulfide derivatives containing 1,3,4-oxadiazole rings with insecticidal activity, a preparation method thereof and the Application of a series of derivatives in the preparation of natural product insecticides. Background technique [0002] [0003] Nootkatone, also known as pomelo ketone, cedarone, the English name is (+)-Nootkatone, the system name is (4R,4aS,6R)-4,4a,5,6,7,8-hexahydro-4 ,4a-Dimethyl-6-(1-methylvinyl)-naphthen-2(3H)-one, a bicyclic sesquiterpene ketone belonging to the Yarcanane series. The pure product of nokadone is a white crystal with a pungent fragrance. Erdtman, H. and Hirose, Y. In 1962, nokatone was first isolated from the heartwood of the Alaskan cork Callitropsis nootkatensis. [0004] Studies in recent years have shown that nokadone has a wide range of biological activities, including ins...

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Problems solved by technology

In addition, studies have shown that nokadone has an anti-proliferative effect [Gliszczyńska A, A, Janeczko T, et al. Microbial transformation of (+)-nootkatone and the antiproliferative activity of its metabolites [J]. Bioorganic & Medicinal Chemistry, 2011, 19 (7): 2464-2469.], anti-platelet aggregation effect [Seo E J, Lee D U, Kwak J H, et al.Antiplatelet effects of Cyperus rotundus and its component(+)-nootkatone[J].Journal ofEthnopharmacology,2011,135(1):48-54.] and anti-obesity effects[Murase T,Misawa K, HaramizuS, et al. Nootkatone, a characteristic constituent of grapefruit, stimulates energy metabolism and prevents diet-induced obesity by activating AMPK [J]. American Journal of Physiology-Endocrinology and Metabolism, 2010, 299(2): E256-E27 , there are few studies on the structure optimization and derivative synthesis of nokadone

Although nokatone parent has a certain insecticidal activity, its insecticidal action spectrum is narrow, mainly targeting vector insects, such as mosquitoes and ticks, and its activity is general, mainly for repellent activity, which is difficult to meet market demand, so it is structured Optimization, in order to develop nokatone derivatives with better insecticidal properties, and prepare natural product insecticides with better efficacy and less toxicity

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