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, 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.
Highlights
Chitin, the β-(1→4) glycoside polymer of N-acetyl-D-glucosamine, is a major structural component of insect cuticles
An effort of structure optimization was carried out, in which the urea linkage was converted to a semicarbazide, while the aniline part was replaced with a 5-phenyl-2-furoyl group (Scheme 1)
All of the title compounds were prepared by the nucleophilic addition reaction of 5-substituted aryl-2-furoyl hydrazine with benzoyl isocyanate under an anhydrous atmosphere
Summary
The β-(1→4) glycoside polymer of N-acetyl-D-glucosamine, is a major structural component of insect cuticles. In addition to the insect cuticles, chitin is present in cell walls of fungi and protozoa, but is absent in higher plants and vertebrates This species-specificity provides the rationale to select chitin as a safe target for pest control agents [1,2]. Benzoylphenylureas (BPUs) have been developed as a typical kind of chitin synthesis inhibitors since Dimilin (diflubenzuron) was introduced into market in the 1970s [3,4]. Their general structures A (Scheme 1) consist of three parts including the benzoyl (X), the urea linkage (Y), and the aniline (Z) [7].
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