Synthesis and Larvicidal Activity of Palmarumycin B6 Analogues

doi:10.6023/cjoc202109018

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (2): 519-525.DOI: 10.6023/cjoc202109018 Previous Articles Next Articles

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Palmarumycin B₆类似物的合成及杀蚊活性

刘鑫磊, 许磊川, 安鑫鲲, 蒋家珍, 王明安^*()

中国农业大学应用化学系农药创新研究中心北京 100193

收稿日期:2021-09-13 修回日期:2021-09-29 发布日期:2022-02-24
通讯作者: 王明安
基金资助:
国家自然科学基金(21772229)

Synthesis and Larvicidal Activity of Palmarumycin B₆ Analogues

Xinlei Liu, Leichuan Xu, Xinkun An, Jiazhen Jiang, Ming'an Wang()

Innovation Center of Pesticide Research, Department of Applied Chemistry, China Agricultural University, Beijing 100193

Received:2021-09-13 Revised:2021-09-29 Published:2022-02-24
Contact: Ming'an Wang
Supported by:
National Natural Science Foundation of China(21772229)

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Abstract

In order to improve the biological activity of naturally occurring Palmarumycin B₆, the synthesis of Palmarumycin B₆ chlorine- and fluorine-containing analogues at A ring has been achieved via ketalization of substituted 1-tetralone enol ether with 1,8-dihydroxynaphthalene and the benzyl oxidation involving pyridinium dichromate and t-BuOOH as the key steps. Their structures were fully characterized by ¹H NMR, ¹³C NMR, and HR-ESI-MS data. Their larvicidal activities were evaluated and showed that 6-chloro-5-hydroxy-2,3-dihydro-4H-spiro[naphthalene-1,2'-naphtho[1,8-de]-[1,3]dioxin]-4-one (4m) and 6-fluoro-5-hydroxy-2,3-dihydro-4H-spiro[naphthalene-1,2'-naphtho[1,8-de][1,3]dioxin]-4-one (4i) were the most active compounds with the LC₅₀values of 11.51 and 23.25 µg/mL against Aedes albopictus, and they would be the potential lead structure to be optimized. The halogen atoms at C-6, 5-hydroxy and 4-carbonyl play a critical role for the larvicidal activities of this type of Palmarumycin B₆ analogues.

Key words: spirobisnaphthalene, Palmarumycin B6, ketalization, benzyl oxidation, larvicidal activity

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Xinlei Liu, Leichuan Xu, Xinkun An, Jiazhen Jiang, Ming'an Wang. Synthesis and Larvicidal Activity of Palmarumycin B₆ Analogues[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 519-525.

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Fig. & Tab. 5

Figure 1. Representing naturally occurring spirobisnaphthalene synthesized in our laboratory[22⇓-24]

Scheme 1. Design strategy of Palmarumycin B6 chlorine- and fluorine-containing analogues

Scheme 3. Synthesis exploration of Palmarumycins B6 6,8- dihalogen analogues

Scheme 4. Structures of Palmarumycins B6, its regioisomer and their synthetic intermediates[23]

Compd.	LC₅₀	Compd.	LC₅₀	Compd.	LC₅₀
3a	>200	4a	>200	4j	97.08
3b	>200	4b	187.24	4k	67.36
3c	>200	4c	>200	4l	130.27
3d	>200	4d	>200	4m	11.51^[23]
3e	>200	4e	155.49	4n	80.11^[23]
3f	143.28	4f	127.61	Rotenone	3.75
3g	>200	4g	170.53	Juglone	6.19
3h	122.17	4h	82.31
3i	>200	4i	23.25

Table 1. LC50 (µg/mL) values for larvicidal activity against A. albopictus of the title compounds 3 and 4

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Palmarumycin B₆类似物的合成及杀蚊活性

Synthesis and Larvicidal Activity of Palmarumycin B₆ Analogues

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Palmarumycin B6类似物的合成及杀蚊活性