1620883-53-5

Upstream product

• 2749-59-9 1,3-dimethyl-5-pyrazolone 
• 109925-18-0 1,3-dimethyl-5-o-tolyloxy-1H-pyrazole-4-carbaldehyde 
• 27006-76-4 5-chloro-4-formyl-1,3-dimethylpyrazole 

Downstream Products

• 1620883-65-9 C₂₄H₂₃ClN₄O₃S 

Relevant academic research and scientific papers

Excellent antitumor and antimetastatic activities based on novel coumarin/pyrazole oxime hybrids

A series of hybrids 10a-v based on coumarin/pyrazole oxime have been synthesized, and exhibit good to excellent antitumor activities. Compound 10n has shown remarkable anticancer effect on SMMC-7721 cells (IC50 = 2.08 μM), which is considerably lower than 5-FU (IC50 = 37.8 μM) and similar to ADM (IC50 = 2.67 μM), with little effect on normal hepatic cells LO2. Notably, the suppression experiments of metastatic activities reveal that 10n also displays significant anti-metastasis effects through inhibiting cell migration and invasion in highly metastatic SMMC-7721 cell line, and dose-dependently reverses TGF-β1-induced epithelial-mesenchymal transition (EMT) procedure better than ADM. Finally, 10n also possesses low acute toxicity and potent tumor growth inhibitory property against SMMC-7721 cell lines in vivo. Our findings suggest that novel coumarin/pyrazole oxime hybrids are promising therapeutic agent candidates for further research.

Development of novel bis-pyrazole derivatives as antitumor agents with potent apoptosis induction effects and DNA damage

A series of bis-pyrazole derivatives were designed and synthesized, and their antitumor effects in vitro and in vivo were investigated. Several compounds displayed good antiproliferative activity with IC50 values in low-micromolar range against three human cancer cell lines in vitro, superior to 5-FU. The most potent compound 10M selectively inhibited human hepatocellular carcinoma cells but not non-tumor liver cell proliferation in vitro, and significantly triggered SMMC-7721 cell apoptosis by cleavage of both PARP and caspase-3 in a concentration-dependent manner. Further study revealed that the potent activity in the cell growth inhibition and apoptosis induction effects of 10M were related to DNA damage and activation of the p53 signaling pathway. Moreover, 10M showed low acute toxicity to mice and significant growth inhibition of the hepatoma tumor in vivo.

Design, synthesis and bioactivities of novel isoxazole-containing pyrazole oxime derivatives

In this study, in order to find novel biologically active pyrazole oxime derivatives, twenty-eight new pyrazole oxime compounds containing a substituted isoxazole ring were synthesized and evaluated for their acaricidaland insecticidal activities. Bioassays exhibited that some target compounds indicated good acaricidal and insecticidal activities against Tetranychus cinnabarinus, Aphis medicaginis, Mythimna separata, and Nilaparvata lugens. Especially, compounds 9c, 9h, 9u, and 9v showed 100.00%, 90.56%, 90.78%, and 90.62% insecticidal activities against A. medicaginis at the concentration of 20 μg/mL, respectively, compounds 9k and 9u had 70.86% and 100.00% insecticidal activities against M. separata at 20 μg/mL, respectively.

Synthesis and bioactivities of novel pyrazole oxime derivatives containing a 1,2,3-thiadiazole moiety

A series of new pyrazole oxime compounds bearing a 1,2,3-thiadiazole ring were designed, synthesized, and evaluated for their insecticidal, acaricidal and antitumor activities. Bioassays demonstrated that some title compounds displayed satisfactory insecticidal and acaricidal properties. Especially, compounds 8d and 8h exhibited 90% insecticidal activities against Aphis craccivora at the concentration of 100?μg/mL. Interestingly, some of the target compounds possessed significant antitumor activities against four human cancer cell lines in vitro. Among them, compounds 8e (IC50?=?7.19?μM), 8l (IC50?=?6.56?μM), 8m (IC50?=?8.12?μM), and 8r (IC50?=?7.06?μM) had better inhibitory activities against HCT-116 cells than the control 5-fluorouracil (IC50?=?29.50?μM). Additionally, compounds 8j, 8m, and 8r showed wonderful inhibitory activities against SGC-7901 cells with the IC50values of 11.46, 9.41, and 8.64?μM, respectively, which were superior to that of the control 5-fluorouracil.

The thiazoylmethoxy modification on pyrazole oximes: Synthesis and insecticidal biological evaluation beyond acaricidal activity

A series of new pyrazole oximes bearing substituted thiazole ring were designed and prepared. The structures of the title compounds were identified by spectral analyses. The results of primary bioassay indicated that some targeted compounds exhibited promising insecticidal activity besides acaricidal activity, particularly; compounds 8c and 8d were more potent against Tetranychus cinnabarinus and Plutella xylostella than other analogues.