Next Article in Journal
Bisbenzamidines as Antifungal Agents. Are Both Amidine Functions Required to Observe an Anti-Pneumocystis carinii Activity?
Previous Article in Journal
Synthesis of Bosutinib from 3-Methoxy-4-hydroxybenzoic Acid
Article Menu

Export Article

Open AccessArticle
Molecules 2010, 15(6), 4267-4282;

Synthesis and Bioactivity of N-Benzoyl-N'-[5-(2'-substituted phenyl)-2-furoyl] Semicarbazide Derivatives

Key Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China
Institute of Vegetables and Flowers, Chinese Academy of Agricultural Science, Beijing 100081, China
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Science, Peking University, Beijing 100083, China
Author to whom correspondence should be addressed.
Received: 5 May 2010 / Revised: 31 May 2010 / Accepted: 2 June 2010 / Published: 11 June 2010
Full-Text   |   PDF [196 KB, uploaded 18 June 2014]   |  


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. View Full-Text
Keywords: chitin synthesis inhibitors; benzoylphenylurea; semicarbazide; synthesis; bioactivity chitin synthesis inhibitors; benzoylphenylurea; semicarbazide; synthesis; bioactivity

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Share & Cite This Article

MDPI and ACS Style

Cui, Z.; Ling, Y.; Li, B.; Li, Y.; Rui, C.; Cui, J.; Shi, Y.; Yang, X. Synthesis and Bioactivity of N-Benzoyl-N'-[5-(2'-substituted phenyl)-2-furoyl] Semicarbazide Derivatives. Molecules 2010, 15, 4267-4282.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top