Synthesis and bioactivity of N-benzoyl-N'-[5-(2'-substituted phenyl)-2-furoyl] semicarbazide derivatives.
Synthesis and bioactivity of N-benzoyl-N'-[5-(2'-substituted phenyl)-2-furoyl] semicarbazide derivatives.
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DOI：
10.3390/molecules15064267
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发表时间：
2010-06-11
期刊：
影响因子：
--
通讯作者：
Yang X
中科院分区：
文献类型：
--
作者：
Cui Z;Ling Y;Li B;Li Y;Rui C;Cui J;Shi Y;Yang X
为了寻找具有良好活性的新型甲壳素合成抑制剂，以典型的甲壳素合成抑制剂苯甲酰基苯脲为先导化合物，通过将苯甲酰基苯脲的脲键转化为氨基脲，将苯胺部分转化为呋喃酰基，设计了15种新型含呋喃基团的甲壳素合成抑制剂。以5-取代苯基-2-呋喃甲酰肼和取代苯甲酰基异氰酸酯为原料合成了标题化合物（化合物E2），其结构经IR、1H-NMR、元素分析和单晶X-射线衍射分析确证。生物活性测定结果表明，目标化合物具有良好的杀虫活性，特别是对小菜蛾，但杀菌活性较低。这些化合物对人早幼粒细胞白血病细胞（HL-60）具有明显的抗肿瘤活性，部分化合物对人肝癌细胞（Bel-7402）、人胃癌细胞（BGC-823）和人鼻咽癌细胞（KB）也具有一定的抗肿瘤活性。结果表明，先导化合物中的键对活性和光谱有重要影响。对脲键的修饰是发现新农药和新药物的有效策略。
In order to find novel chitin synthesis inhibitors (CSIs) with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 15 novel derivatives containing furan moieties were designed by converting the urea linkage of benzoylphenylureas into a semicarbazide and changing the aniline part into furoyl groups. The title compounds were synthesized by the reaction of substituted benzoyl isocyanates with 5-(substituted phenyl)-2-furoyl hydrazine, and the structures were confirmed by IR, 1H-NMR, elemental analysis and single crystal X-ray diffraction analyses (compound E2). The bioassay results indicated that the title compounds exhibit good insecticidal activity, especially towards Plutella xylostella L., but had lower fungicidal activity. Inspiringly, the title compounds possessed obvious anticancer activity against human promyelocytic leukemic cell line (HL-60), and some of the title compounds also had activity against human hepatocellular carcinoma cell line (Bel-7402), human gastric carcinoma cell line (BGC-823), and human nasopharyngeal carcinoma cell line (KB). The results indicated that the linkage in the lead compounds was important to the bioactivity and spectra. The modification on the urea linkage is an effective strategy to discover new pesticide and drug candidates.
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DOI：
10.1093/jnci/83.11.757
发表时间：
1991-06-05
期刊：
JOURNAL OF THE NATIONAL CANCER INSTITUTE
影响因子：
--
作者：
MONKS, A;SCUDIERO, D;BOYD, M
通讯作者：
BOYD, M
影响因子：
4.1
作者：
Cohen, E
通讯作者：
Cohen, E
影响因子：
6.1
作者：
TECLE, B;RUZO, LO;CASIDA, JE
通讯作者：
CASIDA, JE
影响因子：
7.3
作者：
Ren, SJ;Wang, R;Lien, EJ
通讯作者：
Lien, EJ
影响因子：
6.1
作者：
Li, Ying;Li, Bao-Ju;Yang, Xin-Ling
通讯作者：
Yang, Xin-Ling