109925-11-3

Basic information

• Product Name: 5-(2-CHLOROPHENOXY)-1,3-DIMETHYL-1H-PYRAZOLE-4-CARBALDEHYDE
• Synonyms: 5-(2-CHLOROPHENOXY)-1,3-DIMETHYL-1H-PYRAZOLE-4-CARBALDEHYDE
• CAS NO: 109925-11-3
• Molecular Formula: C₁₂H₁₁ClN₂O₂
• Molecular Weight: 250.68
• Mol File: 109925-11-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-(2-CHLOROPHENOXY)-1,3-DIMETHYL-1H-PYRAZOLE-4-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-CHLOROPHENOXY)-1,3-DIMETHYL-1H-PYRAZOLE-4-CARBALDEHYDE(109925-11-3)
• EPA Substance Registry System: 5-(2-CHLOROPHENOXY)-1,3-DIMETHYL-1H-PYRAZOLE-4-CARBALDEHYDE(109925-11-3)

Safety Data

• Hazardous Substances Data: 109925-11-3(Hazardous Substances Data)

Upstream product

• 5203-77-0 1,3-dimethyl-1H-pyrazol-5-ol 
• 95-57-8 2-monochlorophenol 
• 27006-76-4 5-chloro-4-formyl-1,3-dimethylpyrazole 

Downstream Products

• 1424329-90-7 C₂₂H₂₃ClN₄O₂ 
• 1152568-23-4 C₁₂H₁₁ClN₂O₃ 

Relevant articles and documents

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 biological activities of novel pyrazole oxime compounds containing a substituted pyridyl moiety

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).

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 evaluation of anticonvulsant activities of pyrazol semicarbazones. Part II

A series of 2-((5-aryloxy-1-methyl-3-methyl-1H-pyrazol-4-yl)methylene) hydrazinecarboxamides (6a-6l) and 2-((5-aryloxy-1-methyl-3-phenyl-1H-pyrazol-4-yl)methylene) hydrazinecarboxamides (7a-7l) were designed and synthesized. The maximal electroshock shock (MES) and subcutaneous pentylenetetrazole (sc-PTZ) seizure models in mice were used to evaluate the antiepileptic effect of compounds synthesized. Further, the acute neurotoxicity profile was also studied via the rotarod test. The results of sc-PTZ test indicate that a majority of compounds possessed anticonvulsant activity with long duration of protection effects. Among of them, compound 6k was found to be the most promising one, with an ED50 value of 20.4 mg/kg (in sc-PTZ model) and a PI value of 10.8, possessing higher anti-PTZ activity and wider safety margin than valproate and ethosuximide.

Synthesis and bioactivities of novel pyrazole oxime derivatives containing a 5-trifluoromethylpyridyl moiety

In this study, in order to find novel biologically active pyrazole oxime compounds, a series of pyrazole oxime derivatives containing a 5-trifluoromethylpyridyl moiety were synthesized. Preliminary bioassays indicated that most title compounds were found to display good to excellent acaricidal activity against Tetranychus cinnabarinus at a concentration of 200 μg/mL, and some designed compounds still showed excellent acaricidal activity against Tetranychus cinnabarinus at the concentration of 10 μg/mL, especially since the inhibition rates of compounds 8e, 8f, 8l, 8m, 8n, 8p, and 8q were all 100.00%. Interestingly, some target compounds exhibited moderate to good insecticidal activities against Plutella xylostella and Aphis craccivora at a concentration of 200 μg/mL; furthermore, compounds 8e and 8l possessed outstanding insecticidal activities against Plutella xylostella under the concentration of 50 μg/mL.

Synthesis and biological activities of novel 1,3,4-thiadiazole-containing pyrazole oxime derivatives

A new library of 1,3,4-thiadiazole-containing pyrazole oximes was designed and synthesized. Their acaricidal and insecticidal activities were evaluated. Bioassay results indicated that some target compounds exhibited good acaricidal and insecticidal properties. Especially, compound 8m had 80% acaricidal activity against Tetranychus cinnabarinus at the concentration of 50?μg/mL, compound 8f displayed 100% insecticidal activities against Aphis craccivora at the concentration of 50?μg/mL, compounds 8r and 8w showed 100% insecticidal activities against Plutella xylostella at the concentration of 50?μg/mL. Furthermore, compounds 8r (LC50?=?19.61?μg/mL) and 8w (LC50?=?9.78?μg/mL) possessed comparable or even better insecticidal activities than the control Pyridalyl (LC50?=?17.40?μg/mL) against P. xylostella.

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.

Design, synthesis and bioactivities of novel dichloro-allyloxy-phenol-containing pyrazole oxime derivatives

In this study, in order to find novel biologically active pyrazole oxime compounds, a number of dichloro-allyloxy-phenol-containing pyrazole oximes were designed and synthesized according to the method of active group combination. All of the target compounds were confirmed by 1H-NMR, 13C-NMR and elemental analysis. In addition, bioassays showed that all of the newly synthesized compounds had no acaricidal activity against Tetranychus cinnabarinus and low insecticidal activity against Aphis craccivora at tested concentrations. However, most of them displayed excellent insecticidal activity against Oriental armyworm at a concentration of 500 μg/mL, and some designed compounds still exhibited potent insecticidal activity against Oriental armyworm even at the dose of 20 μg/mL, especially compounds 7f, 7n and 7p had 100%, 90% and 90% inhibition rates, respectively, which were comparable to that of the control pyridalyl.

Discovery of 5-phenoxy-1,3-dimethyl-1H-pyrazole-4-carboxamides as potent agonists of TGR5 via sequential combinatorial libraries

Optimization of a high-throughput screening hit led to the discovery of a new series of 5-phenoxy-1,3-dimethyl-1H-pyrazole-4-carboxamides as highly potent agonists of TGR5. This novel chemotype was rapidly developed through iterative combinatorial library synthesis. It was determined that in vitro agonist potency correlated with functional activity data from human peripheral blood monocytes.