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Synthesis and Bioactivity of N-Benzoyl-N ′-[5-(2 ′-substituted phenyl)-2-furoyl] Semicarbazide Derivatives
Cui, Zining1; Ling, Yun1; Li, Baoju2; Li, Yongqiang1; Rui, Changhui1; Cui, Jingrong3; Shi, Yanxia2; Yang, Xinling1
关键词Chitin Synthesis Inhibitors Benzoylphenylurea Semicarbazide Synthesis Bioactivity
刊名MOLECULES
2010-06-01
DOI10.3390/molecules15064267
15期:6页:4267-4282
收录类别SCI
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
研究领域[WOS]Chemistry
关键词[WOS]QUANTITATIVE STRUCTURE-ACTIVITY ; INSECT GROWTH-REGULATORS ; BENZOYLPHENYLUREAS ; SUBSTITUENTS ; DESIGN
英文摘要

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, (1)H-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.

语种英语
WOS记录号WOS:000279207300032
项目编号2006AA10A201 ; 2010CB126104 ; 20972185
资助机构National High Technology Research and Development Program of China ; National Key Project for Basic Research ; National Natural Science Foundation of China ; Scientific Research Foundation of the Graduate School of China Agricultural University
引用统计
被引频次:14[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/52989
专题北京大学药学院
北京大学药学院_分子与细胞药理学系
作者单位1.China Agr Univ, Dept Appl Chem, Coll Sci, Key Lab Pesticide Chem & Applicat,Minist Agr, Beijing 100193, Peoples R China
2.Chinese Acad Agr Sci, Inst Vegetables & Flowers, Beijing 100081, Peoples R China
3.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100083, Peoples R China
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GB/T 7714
Cui, Zining,Ling, Yun,Li, Baoju,et al. Synthesis and Bioactivity of N-Benzoyl-N ′-[5-(2 ′-substituted phenyl)-2-furoyl] Semicarbazide Derivatives[J]. MOLECULES,2010,15(6):4267-4282.
APA Cui, Zining.,Ling, Yun.,Li, Baoju.,Li, Yongqiang.,Rui, Changhui.,...&Yang, Xinling.(2010).Synthesis and Bioactivity of N-Benzoyl-N ′-[5-(2 ′-substituted phenyl)-2-furoyl] Semicarbazide Derivatives.MOLECULES,15(6),4267-4282.
MLA Cui, Zining,et al."Synthesis and Bioactivity of N-Benzoyl-N ′-[5-(2 ′-substituted phenyl)-2-furoyl] Semicarbazide Derivatives".MOLECULES 15.6(2010):4267-4282.
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