Synthesis and Biological Activities of Novel Cyanoacrylates Containing 1,3,4-Oxadiazole Moiety

Abstract

In order to find new cyanoacrylate lead compounds, a series of novel cyanoacrylates carrying 1,3,4-oxadiazole moiety were prepared by the method of active substructure combination. The structures of the title compounds were characterized by 1 H NMR, 13 C NMR and elemental analysis. Preliminary bioassay data displayed that in postemergence treatment compound 8b had 80% herbicidal activity against Stellaria media at 1500 g/ha and compound 8j showed 70% herbicidal activity against Chenopodium serotinum L. at 1500 g/ha. Additionally, compounds 8e, 8k, 8m and 8n exhibited good anti-tumor activity against HepG2 cells with the IC 50 values of 8.2, 5.9, 8.0 and 12.6 μmol/L, respectively.

Synthesis and In Vitro and In Vivo Biological Activity Evaluation and Quantitative Proteome Profiling of Oxadiazoles Bearing Flexible Heterocyclic Patterns

“…As another attractive building block, furan or tetrahydrofuran motifs were also utilized to decorate and functionalize the target compounds, which consequently showed the broad-spectrum biological effects of these integrated molecules − such as commercial antifungal agents cyclafuramid, fenfuram, furcarbanil, and methfuroxam, the antibiotic drug furamizole, and the insecticidal agent dinotefuran . Additionally, 1,3,4-oxadiazole scaffold, which serves as a promising fragment, has been extensively explored to innovate the biopharmaceutical activities of the final integrated structures. ,,− Its derivatives have prospective applications in various aspects including herbicide (oxadiazon), insecticide (metoxadiazone), and anti-HIV (raltegravir) . Moreover, our previous works had synthesized and identified a series of 1,3,4-oxadiazole sulfone derivatives that possessed good antiviral and antibacterial activities.…”

Synthesis and Herbicidal Activity of Novel Cyanoacrylates Containing Substituted Pyridyl Moiety

“…初步的 生测结果表明, 在 1500 g•ha 1 测试剂量下, 化合物 7l 对 芥菜的茎叶处理除草效果较好, 抑制率为 95%; 化合物 7e, 7l 和 7m 对繁缕的茎叶处理除草活性相对较高, 抑制 率分别为 80%, 80%和 100%; 此外, 化合物 7b, 7l 和 7m 对小藜的茎叶处理除草活性均为 100%, 与对照药 NK-9717 的除草活性相当, 具有进一步研究的价值. 试验方法: 盆栽法(普筛), 苗前土壤处理和苗后茎 叶处理 [21] . 供试靶标为芥菜、繁缕和小藜.…”

Design, Synthesis, and Biological Activities of Novel 2-Cyanoacrylate Compounds Containing Substituted Pyrazolyl or 1,2,3-Triazolyl Moiety

“…Recently, Wang et al reported that isoxazole-containing 2-cyanoacrylate compound A ( Figure 1 ) had significant herbicidal activity [ 10 ], Zhao et al obtained 2-cyanoacrylate compound B ( Figure 1 ) with a substituted oxazole moiety possessing interesting plant growth regulatory effect in addition to excellent herbicidal activity [ 11 ]. More recently, Shi and co-workers found that 1,3,4-oxadiazole-containing 2-cyanoacrylate analogue C ( Figure 1 ) exhibited vital antitumor properties against human hepatoma cells [ 12 ]. This strongly promoted the research of bioactive molecules containing the 2-cyanoacrylate subunit.…”