Page 168 - 《精细化工》2020年第9期

·1882· 精细化工 FINE CHEMICALS 第 37 卷

Ⅲd、Ⅳa 和Ⅳd 对层出镰刀菌的抑制率能达到 59.0% progress of microbial fungicides for planting[J]. Modern Agriculture
(现代化农业), 2019, 8: 62-63.
以上；尽管目标化合物对立枯丝核菌的抑制效果较 [3] FU Y (付炎), WANG Y F (王于方), LI L G (李力更), et al.
小，但还是能看出，苯环上含给电子基团的化合物 Historical story on natural medicinal chemistry: Natural products
research and Nobel Prize[J]. Chinese Traditional and Herbal Drugs
具有更高的抑制活性，其中，化合物Ⅲb 对其抑制 (中草药), 2016, 47(21): 3749-3765.
率为 60.3%。以上结果可能是由于化合物苯环上的 [4] HU D Y (胡冬英), XU D M (徐大满), CHU M L (储梦龙), et al. A
review of the main chemical constituents of camphor tree essential
给电子基团（2,4,6-三甲基或 2,6-二异丙基）都是烷 oil[J]. Chemicals and Industry of Forest Products (林产化学与工业),
基结构，具有更强的亲脂性，能引起细胞膜损伤， 2019, 56(11): 61-64.
[5] WANG C X, LI M, ZHANG L P, et al. Properties of camphor
进而导致其无法正常生长乃至死亡，达到抑菌的效果。 oil/poly (methyl methacrylate) composites and their application on
cotton fabrics[J]. Textile Research Journal, 2017, 87(11): 1318-1325.
表 1 樟脑基咪唑盐类化合物对 3 种植物病原菌的抑制率 [6] MOAYEDI Y, GREENBERG S A, JENKINS B A, et al. Camphor
Table 1 Inhibition rates of camphor-based imidazolium salts white oil induces tumor regression through cytotoxic T cell-dependent
on three plant pathogens mechanisms[J]. Molecular Carcinogenesis, 2019, 58(5): 722-734.
[7] SOKOLOVA A S, YAROVAYA O I, SHERNYUKOV A V, et al.
抑制率/% Discovery of a new class of antiviral compounds: Camphor imine
化合物
灰葡萄球菌 层出镰刀菌 立枯丝核菌 derivatives[J]. European Journal of Medicinal Chemistry, 2015, 105:
263-273.
Ⅲa 94.9 40.8 22.7
[8] TRAN T A, HO M T, SONG Y W, et al. Camphor induces
Ⅲb 98.0 59.0 60.3 proliferative and anti-senescence activities in human primary dermal
Ⅲc 91.8 28.6 34.1 fibroblasts and inhibits UV-induced wrinkle formation in mouse
Ⅲd 100.0 66.2 54.1 skin[J]. Phytotherapy Research, 2015, 29(12): 1917-1925.
[9] SOKOLOVA A S, YAROVAYA O I, SHERNYUKOV A V, et al.
Ⅳa 91.8 70.4 45.5
New quaternary ammonium camphor derivatives and their antiviral
Ⅳb 87.8 34.7 47.7 activity, genotoxic effects and cytotoxicity[J]. Bioorganic & Medicinal
Ⅳc 83.7 40.8 22.7 Chemistry, 2013, 21(21): 6690-6698.
[10] PERAMAN R, TIWARI A K, VANI M G, et al. New camphor
Ⅳd 89.8 60.1 45.5
hybrids: Lipophilic enhancement improves antimicrobial efficacy
Ⅴa 100.0 51.0 47.7 against drug-resistant pathogenic microbes and intestinal worms[J].
Ⅴb 81.6 26.5 13.6 Medicinal Chemistry Research, 2018, 27(6): 1728-1739.
Ⅴc 57.1 20.4 18.2 [11] CARVALHO M F N N, HERRMANN R, MARQUES F, et al.
Search for cytotoxic compounds against ovarian cancer cells:
Ⅴd 61.2 30.6 13.6
Synthesis, characterization and assessment of the activity of new
Ⅵa 51.0 26.5 34.1 camphor carboxylate and camphor carboxamide silver complexes[J].
Ⅵb 55.1 32.7 22.7 Journal of Inorganic Biochemistry, 2018, 188: 88-95.
Ⅵc 49.0 28.6 11.4 [12] LI K, SHI D Q. Synthesis and herbicidal activity of 3-aryl-1-[2-
(aryloxy)propanoyl] imidazolidine-2,4-diones[J]. Journal of Heterocyclic
Ⅵd 56.6 35.2 30.0 Chemistry, 2009, 46(3): 544-547.
百菌清 86.7 65.5 75.0 [13] FANG Y, YUAN R, GE W H, et al. Synthesis and biological
evaluation of 1,2,4,5-tetrasubstituted imidazoles[J]. Research on
Chemical Intermediates, 2017, 43(8): 4413-4421.
3 结论 [14] MARZOUK A A, ABDELHAMID A A, MOHAMED S K, et al.
Morpholinium hydrogen sulfate (MHS) ionic liquid as an efficient
catalyst for the synthesis of bioactive multi-substituted imidazoles
以樟脑磺酸为原料，制得 10-碘代樟脑后，与不 (MSI) under solvent-free conditions[J]. Zeitschrift Fur Naturforschung
同取代的芳基咪唑发生季铵化反应，进一步通过离 B, 2017, 72(1): 23-33.
[15] SHALMALI N, ALI M R, BAWA S. Imidazole: An essential edifice
子交换，最终得到 16 种相应的樟脑基咪唑盐。 for the identification of new lead compounds and drug development[J].
抑菌活性结果表明：在质量浓度为 500 mg/L Mini Reviews in Medicinal Chemistry, 2017, 18(2): 142-163.
[16] ODŽAK R, SKOČIBUŠIĆ M, MARAVIĆ A. Synthesis and
时，目标化合物对灰葡萄球菌、层出镰刀菌和立枯 antimicrobial profile of N-substituted imidazolium oximes and their
丝核菌均具有一定的抑菌活性。其中，部分目标化 monoquaternary salts against multidrug resistant bacteria[J]. Bioorganic
& medicinal chemistry, 2013, 21(23): 7499-7506.
合物对灰葡萄球菌的抑制活性普遍优于百菌清，Ⅲd、 [17] HRYNIEWICKA A, MALINOWSKA M, HAUSCHILD T, et al.
Ⅴa 对其抑制率可达 100%；化合物Ⅲd、Ⅳa 对层出 Synthesis and antimicrobial properties of steroid-based imidazolium
salts[J]. The Journal of Steroid Biochemistry and Molecular Biology,
镰刀菌有较好的抑制活性，抑制率分别为 66.2%、 2019, 189: 65-72.
70.4%，效果与阳性药百菌清相近；受试化合物对立 [18] ZHANG J H ( 张君辉 ). Synthesis and fungicidal activity of
benzoyloxyacetamino/imidazolidinones based on pyridine moiety[D].
枯丝核菌具有一定的抑制效果，但整体抑制率不及 Taian: Shandong Agriculture University (山东农业大学), 2015.
百菌清。 [19] RIČKO S, PERDIH A, SVETE J, et al. 1,3-Diamine-derived
bifunctional organocatalyst prepared from camphor[J]. Advanced
Synthesis & Catalysis, 2016, 358(23): 3786-3796.
参考文献：
[20] LIU J P, CHEN J B, ZHAO J F, et al. A modified procedure for the
[1] WEN T Y (温彤玥), ZHONG K (钟凯), LIU R J (刘润进). Effects of synthesis of 1-arylimidazoles[J]. Chem Inform, 2003, 35(17): 2661-2666.
some climate change factors on mycorrhizal fungi[J]. Journal of [21] DING CH R (丁成荣), PAN Y Y (潘亚运), YIN X (殷许), et al.
Qingdao Agricultural University (Natural Science Edition) (青岛农 Synthesis and biological activity of thiazolidine piperidine
业大学学报: 自然科学版), 2015, 32(4): 235-241. nicotinamide compounds[J]. Chinese Journal of Organic Chemistry
[2] LIU J S (刘建生), YU W Q (于文清), HE D (贺丹), et al. Research (有机化学), 2019, 39(7): 2099-2105.