Design, Synthesis, and Biological Activities of Novel Pyrazole Oxime Compounds Containing a Substituted Pyridyl Moiety.

Cuili Chen,Ning Bao,Jia Chen,Hong Dai,Haiying Gu

doi:10.3390/molecules22060878

Cuili Chen, Ning Bao + Show 3 more

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https://doi.org/10.3390/molecules22060878

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Abstract

In this paper, in order to find novel biologically active pyrazole oximes, a series of pyrazole oxime compounds bearing a substituted pyridyl unit were prepared. Bioassays showed that some target compounds were found to have good acaricidal activity against Tetranychus cinnabarinus at a concentration of 500 μg/mL, compound 9q especially displayed potent acaricidal activity against T. cinnabarinus when the concentration was reduced to 100 μg/mL. Interestingly, most target compounds possessed excellent insecticidal activities against Oriental armyworm at 500 μg/mL. Moreover, some compounds were active against Aphis medicaginis and Nilaparvata lugens at 500 μg/mL. Additionally, compounds 9b, 9g, 9l, 9p, 9q, 9r, 9s, 9t, 9u, and 9v displayed significant antiproliferative activities against HepG2 cells with IC50 values of 1.53–17.27 μM, better than that of the control 5-fluorouracil (IC50 = 35.67 μM).

Highlights

In the past few decades, heterocycles play a significant role in the research of agricultural and medicinal chemistry
Zou et al reported that thiazole-containing pyrazole oxime compound A (Figure 1) displayed good insecticidal activity [7], Dai et al obtained pyrazole oxime compound B (Figure 1) bearing a benzyloxy-linked thiazole unit exhibiting interesting insecticidal activity besides good acaricidal activity [8]
Pyrazole oxime compounds became a focus of chemical and pharmaceutical research

Summary

Introduction

In the past few decades, heterocycles play a significant role in the research of agricultural and medicinal chemistry. Fenpyroximate (Figure 1), a potent acaricide carrying a pyrazole oxime unit, is used to control some important phytophagous mites such as Tetranychus urticae Koch and Polyphagotarsonemus latus Banks [6]. After it appeared on the market in 1991, many chemists began to study the structural modification of fenpyroximate. Park et al reported some Fenpyroximate analogues possessing potential anticancer properties against HepG2 (human hepatoma) cells [9], and Dai et al found some 1,2,3-thiadiazole-containing pyrazole oxime derivatives displaying satisfactory antitumor activities against Panc-1 (human pancreatic carcinoma) and SGC-7901 (human gastric cancer) cells [10]. Pyrazole oxime compounds became a focus of chemical and pharmaceutical research

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