Page 116 - 201902

·282· 精细化工 FINE CHEMICALS 第 36 卷

表 4 化合物Ⅲa 与Ⅲd 对桃蚜的室内毒力
Table 4 Toxicity of compounds Ⅲa and Ⅲd against Myzus persicae
化合物 R 毒力回归方程 相关系数（r） L C 50/（mg/L）
Ⅲa Cl y = 2.8383 X+0.4221 0.9748 41.0073
Ⅲd CH 3 y = 2.3879 X+1.2426 0.9866 37.4589
吡虫啉 y = 2.0784 X+1.9862 0.9895 28.1854
注：X 为药剂质量浓度的对数值。

由表 3 可知，当质量浓度为 25 mg/L 时，化合 [3] Beaulieu P L, Coulombe R, Duan J, et al. Structure-based design of
novel HCV NS5B thumb pocket 2 allosteric inhibitors with
物Ⅲa 与Ⅲd 的致死率均为 30%左右，当质量浓度为 submicromolar gt1 replicon potency: discovery of a quinazolinone
50 mg/L 时，致死率明显增加，分别为 73.3%与 chemotype[J]. Bioorganic and Medicinal Chemistry Letters, 2013,
23(14): 4132-4140.
70.9%，当质量浓度增加到 100 mg/L 时，化合物Ⅲa
[4] Sahoo B M, Dinda S C, Ravi Kumar B V, et al. Green Synthesis and
与Ⅲd 的致死率分别为 81.8%和 83.6%，与吡虫啉接 evaluation of 3-(aryl)-2-thioxo-2,3-dihydro-quinazolin-4(1H)-ones as
novel anticonvulsant drugs[J]. International Journal of Nanotechnology,
近。由表 4 可知，化合物Ⅲa 与Ⅲd 的 LC 50 分别为
2013, 6: 2046-2052.
41.0073 与 37.4589 mg/L ，接 近吡虫 啉（ LC 50 = [5] Wang X, Li P, Li Z N, et al. Synthesis and bioactivity evaluation of
novel arylimines containing a 3-aminoethyl-2-[(p-trifluoromethoxy)
28.1854 mg/L）。化合物Ⅲd 的苯环上含有—CH 3 ，其
anilino]-4(3H)-quinazolinone moiety[J]. Journal of Agricultural and
杀桃蚜能力最强。具有类似结构且含有—CH 3 的诺 Food Chemistry, 2013, 61(40): 9575-9582.
蒎酮-吡唑酰胺类衍生物也具有杀虫活性 [16] ，说明苯 [6] Ou Junjun (欧俊军), Liu Kechang (刘克昌), Wang Yi (王毅), et al.
Synthesis and bioactivity studies of 2,3-disubstituted quinazolin- 4
环上—CH 3 取代基有助于提高松节油衍生物的杀虫 (3H)-one[J]. Chinese Journal of Organic Chemistry (有机化学),
活性。 2013, 34(3): 526-536.
[7] Drew L, Engelman J, Katayama R, et al. Concurrent roles for IGF1R
and EGFR in driving acquired resistance to crizotinib and ability to
3 结论 overcome with a combination of the ALK/IGF1R inhibitor AZD3463
and Iressa[J]. Cancer Research, 2013, 73 (8 Supplement): 4465.
以异长叶烷酮为原料，经缩合、环化等反应合 [8] Abera M, Sordella R, Kazanietz M. PKC alpha is implicated in
epithelial to mesenchymal transition and erlotinib resistance in
成了 6 个异长叶烷基-喹唑啉-2-胺衍生物（Ⅲa~Ⅲf）， non-small cell lung carcinoma cells[J]. Cancer Research, 2013, 73(8
13
1
并采用 HNMR、 CNMR、IR、HRMS 等手段对其 Supplement): 5261.
[9] Noolvi M N, Patel H M, Bhardwaj V, et al. Synthesis and in vitro
结 构 进 行了表 征， 考察了 化合 物Ⅲ a~Ⅲ f 的抗 antitumor activity of substituted quinazoline and quinoxaline
HUVECs、HepG2 等细胞的生物活性以及对桃蚜的 derivatives: search for anticancer agent[J]. European Journal of
Medicinal Chemistry, 2011, 46(6): 2327-2346.
抗虫活性。 [10] Wang D W, Lin H Y, Cao R J, et al. Synthesis and herbicidal
（1）采用 MTT 法考察了化合物Ⅲa~Ⅲf 对人 evaluation of triketone-containing quinazoline-2, 4-diones[J]. Journal
of Agricultural and Food Chemistry, 2014, 62(49): 11786-11796.
体肝癌细胞（HepG2）的抗肿瘤活性和对 HUVECs [11] Wu J, Bai S, Yue M, et al. Synthesis and insecticidal activity of 6,8-
的抗炎活性。结果表明，化合物Ⅲa~Ⅲf 对 HUVECs dichloro-quinazoline derivatives containing a sulfide substructure[J].
Chemical Papers, 2014, 68(7): 969-975.
没有明显的抗炎活性，而化合物Ⅲa（IC 50 =8.58± [12] Gao Xingwen (高兴文), Cai Xuejian (蔡学建), Yan Kai (严凯), et al.
0.5 μmol/L）对 HepG2 具有显著的抗肿瘤活性。 Synthesis and anti-tobacco mosaic virus activity of 4(3H)-
quinazolinone Schiff base[J]. Chinese Journal of Organic Chemistry
（2）采用叶浸渍法考察了化合物Ⅲa~Ⅲf 对桃 (有机化学), 2008, 28(10): 1785-1791.
蚜 的 杀 虫活性 。结 果表明 ，化 合物Ⅲ a（ LC 50 = [13] Wang D W, Lin H Y, Cao R J, et al. Design, synthesis and herbicidal
activity of novel quinazoline-2,4-diones as 4-hydroxyphenylpyruvate
41.0073 mg/L）与Ⅲd（LC 50 =37.4589 mg/L）对桃蚜 dioxygenase inhibitors[J]. Pest Management Science, 2015, 71(8):
具有较好的抗虫活性，研究价值较高。 1122-1132.
[14] Bai Yang (白杨), Liu Liujun (刘六军), Zhou Tiaotiao (周调调), et al.
（3）异长叶烷基-喹唑啉-2-胺衍生物在抗肿瘤 The research of isolongifolanone synthesized from longifolene[J]. Fine
和杀虫等方面具有潜在的研究和应用价值。 and Specialty Chemicals (精细与专用化学品), 2011, 19(2): 47-51.
[15] Rui Jian (芮坚), Yang Jinlai (杨金来), Huang Jianfeng (黄建峰), et
参考文献： al. Synthesis, antitumor and anti-inflammatory activities of
isolongifolanonyl pyrazole derivatives[J]. Chinese Journal of Organic
[1] Chen H Y, Jiang Y L, Lin C M, et al. Dual inhibition of EGFR and Chemistry (有机化学), 2016, 36(9): 2183-2190.
c-Met kinase activation by MJ-56 reduces metastasis of HT29 human [16] Rui Jian (芮坚), Zhang Qi (张齐), Wang Xin (王欣), et al. Synthesis
colorectal cancer cells[J]. International Journal of Oncology, 2013, and biological activity of novel pinanyl pyrazole acetamide
43(1): 141-150. derivatives[J]. Chinese Journal of Organic Chemistry (有机化学),
[2] Patel M B, Kumar S P, Valand N N, et al. Synthesis and biological 2017, 37(1): 218-225.
evaluation of cationic fullerene quinazolinone conjugates and their [17] Rui Jian (芮坚), Xu Xu (徐徐), Yang Yiqin (杨益琴), et al. Synthesis
binding mode with modeled Mycobacterium tuberculosis of a novel quinazoline derivative from isolongifolanone[J]. Chemistry
hypoxanthine-guanine phosphoribosyltransferase enzyme[J]. Journal and Industry of Forest Products (林产化学与工业), 2016, 36(4):
of Molecular Modeling, 2013, 19(8): 3201-3217. 121-127.