Synthesis and bioactivity of N-benzoyl-N'-[5-(2'-substituted phenyl)-2-furoyl] semicarbazide derivatives.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Zining CuiXinling Yang

Abstract

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 ure...Continue Reading

References

Jun 5, 1991·Journal of the National Cancer Institute·A MonksA Vaigro-Wolff
Nov 7, 2001·Pest Management Science·E Cohen
Feb 7, 2003·Current Drug Targets. Infectious Disorders·J Ruiz-Herrera, G San-Blas
Jan 6, 2005·Journal of Agricultural and Food Chemistry·Li ChenFuchun Bi
Mar 31, 2009·Journal of Agricultural and Food Chemistry·Ranfeng SunQingmin Wang
Feb 9, 2010·European Journal of Medicinal Chemistry·Nahid NishatShadma Parveen
Feb 16, 2010·Journal of Agricultural and Food Chemistry·Ying LiXin-Ling Yang

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Citations

Nov 9, 2012·Journal of Agricultural and Food Chemistry·Zi-Ning CuiXin-Ling Yang
Apr 24, 2014·International Journal of Molecular Sciences·Zining CuiYoshihiro Nishida
Dec 5, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Guo-Xiang SunYun-Yang Wei
Mar 11, 2016·Scientific Reports·Gao-Peng SongZi-Ning Cui
Oct 26, 2011·Chemical Biology & Drug Design·Zi-Ning CuiXin-Ling Yang

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Methods Mentioned

BETA
X-ray
column chromatography
single crystal diffraction

Software Mentioned

97
SHELXS
SHELXL

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