Page 228 - 《精细化工》2021年第3期

·648· 精细化工 FINE CHEMICALS 第 38 卷

（后二者均为 B 级活性水平）。(E)-Ⅴb 和(Z)-Ⅴc 对 resolution of citral[J]. Helvetica Chimica Acta, 2016, 99(5): 373-377.
[8] HUO X Y, GUO L, CHEN X F, et al. Design, synthesis, and
黄瓜枯萎病菌的相对抑制率均为 73.7%（B 级活性
antifungal activity of novel aryl-1, 2, 3-triazole-β-carboline hybrids[J].
水平）。显然，目标化合物(E)-Ⅴm 对西瓜炭疽病菌 Molecules, 2018, 23(6): 1344-1353.
和玉米小斑病菌的相对抑制率均高达 95.2%（A 级 [9] KHAZIR J, MIR B A, CHASHOO G, et al. Synthesis and anticancer
activity of N-9- and N-7-substituted 1, 2, 3-triazole analogues of 2,
活性水平，优于阳性对照百菌清），值得进一步研究。 6-di-substituted purine[J]. Medicinal Chemistry Research, 2020,
总体上，(E)式比(Z)式异构体抑菌活性要好，且有时 29(1): 33-45.
差异明显，如对西瓜炭疽病菌，(E)-Ⅴm 是(Z)-Ⅴm [10] CHEN X L, XIAO Y X, WANG G L, et al. Synthesis of novel 1, 2,
3-triazole-containing pyridine-pyrazole amide derivatives based on
的 6.7 倍，而对黄瓜枯萎病菌，(E)-Ⅴb 是(Z)-Ⅴb 的 one-pot click reaction and their evaluation for potent nematicidal
13.9 倍。 activity against Meloidogyne incognita[J]. Research on Chemical
Intermediates, 2016, 42(6): 5495-5508.
3 结论 [11] NEJMA A B, ZNATI M, DAICH A, et al. Design and semisynthesis
of new herbicide as 1, 2, 3-triazole derivatives of the natural maslinic
acid[J]. Steroids, 2018, 138: 102-107.
（1）分别将橙花醇和香叶醇氧化为橙花醛和香 [12] SAEEDI M, MOHAMMADI-KHANAPOSHTANI M, POURRABIA
叶醛（柠檬醛的两个立体异构体），再对醛基进行改 P, et al. Design and synthesis of novel quinazolinone-1, 2, 3-triazole
hybrids as new anti-diabetic agents: In vitro α-glucosidase inhibition,
性，合成得到 26 个(Z)-、(E)-柠檬醛基 1,2,3-三唑类 kinetic, and docking study[J]. Bioorganic Chemistry, 2019, 83: 161-
13
1
化合物Ⅴa~m。采用 FTIR、 HNMR、 CNMR 和 169.
ESI-MS 对目标化合物结构进行了表征。 [13] HE Y, DUAN W G, LIN G S, et al. Synthesis and herbicidal activity
of citral-based thiosemicarbazone compounds[J]. Chemistry and
（2）初步的抑菌活性测试表明，在目标化合物 Industry of Forest Products, 2020, 40(3): 76-84.
质量浓度为 50 mg/L 时，(E)-Ⅴm、(E)-Ⅴb 和(Z)-Ⅴ [14] LIN G S, BAI X, DUAN W G, et al. High value-added application of
sustainable natural forest product α-pinene: Synthesis of myrtenal
c 对西瓜炭疽病菌的相对抑制率分别为 95.2%（A 级
oxime esters as potential KARI inhibitors[J]. ACS Sustainable
活性水平，优于阳性对照百菌清）、81.0%（B 级活 Chemistry and Engineering, 2019, 7(8): 7862-7868.
性水平）和 81.0%（B 级活性水平）。此外，(E)-Ⅴm [15] ZHU X P, LIN G S, DUAN W G, et al. Synthesis and antiproliferative
evaluation of novel longifolene-derived tetralone derivatives bearing
对玉米小斑病菌的相对抑制率也高达 95.2%（A 级
1, 2, 4-triazole moiety[J]. Molecules, 2020, 25(4): 986-997.
活性水平，优于阳性对照百菌清）。因此，(E)-Ⅴm [16] LIN G S (林桂汕), MA Y (马媛), DUAN W G (段文贵), et al.
是值得进一步研究的先导化合物。总体上，(E)式比 Synthesis and properties of perillaldehyde-based oxime ester
compounds[J]. Fine Chemicals (精细化工), 2018, 35(8): 1432-1440.
(Z)式异构体抑菌活性要好，且有时差异明显。 [17] HUANG M, DUAN W G, LIN G S, et al. Synthesis and antifungal
activity of novel 3-caren-5-one oxime esters[J]. Molecules, 2017,
致谢：抑菌活性测试由南开大学元素有机化学 22(9): 1538-1552.
国家重点实验室生物活性测试室完成，谨表谢意。 [18] CHEN N Y, DUAN W G, LIN G S, et al. Synthesis and antifungal
activity of dehydroabietic acid-based 1, 3, 4-thiadiazole-thiazolidinone
compounds[J]. Molecular Diversity, 2016, 20(4): 897-905.
参考文献：
[19] MA X L (马献力), LI F Y (李芳耀), DUAN W G (段文贵), et al.
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