380910-52-1

Usage

Chemical class

Pyrazole carboxylic acids

Explanation

1-PHENYL-3-P-TOLYL-1H-PYRAZOLE-4-CARBOXYLIC ACID belongs to the class of pyrazole carboxylic acids due to its pyrazole ring and carboxylic acid functional group.

Explanation

The compound is composed of a pyrazole ring with a carboxylic acid group attached at the 4th position and substituted with phenyl and p-tolyl groups at the 1st and 3rd positions, respectively.

Explanation

1-PHENYL-3-P-TOLYL-1H-PYRAZOLE-4-CARBOXYLIC ACID is often used in pharmaceutical and chemical research as a building block for the synthesis of various biologically active molecules, such as antiviral, antibacterial, and anticancer agents.

Explanation

The compound's unique structure and properties make it a valuable tool in drug discovery and development, as it can be used to create a variety of potentially therapeutic agents.

Structural components

Pyrazole ring, carboxylic acid group, phenyl group, p-tolyl group

Applications

Pharmaceutical and chemical research, synthesis of biologically active molecules

Unique value

Valuable tool in drug discovery and development

InChI:InChI=1/C17H14N2O2/c1-12-7-9-13(10-8-12)16-15(17(20)21)11-19(18-16)14-5-3-2-4-6-14/h2-11H,1H3,(H,20,21)

Upstream product

• 36640-52-5 1-phenyl-3-(p-tolyl)-1H-pyrazole-4-carbaldehyde 
• 100-63-0 phenylhydrazine 
• 122-00-9 para-methylacetophenone 
• 59-88-1 phenylhydrazine hydrochloride 
• 54779-81-6 4-methylacetophenone phenylhydrazone 

Downstream Products

• 380895-12-5 C₂₃H₁₈ClN₃O 
• 379219-07-5 C₂₄H₂₁N₃O₂ 
• 380895-39-6 C₂₃H₁₉N₃O 
• 1380571-31-2 N-(4-ethoxyphenyl)-1-phenyl-3-(p-tolyl)-1H-pyrazole-4-carboxamide 
• 380895-19-2 C₂₃H₁₈BrN₃O 

Relevant academic research and scientific papers

Synthesis of lathyrane diterpenoid nitrogen-containing heterocyclic derivatives and evaluation of their anti-inflammatory activities

As our ongoing work on lathyrane diterpenoid derivatization, three series of lathyrane diterpenoid derivatives were designed and synthesized based combination principles, including pyrazole, thiazole and furoxan moieties. Biological evaluation indicated t

Pd-catalyzed post-Ugi intramolecular cyclization to the synthesis of isoquinolone-pyrazole hybrid pharmacophores & discover their antimicrobial and DFT studies

A novel microwave assisted ligand-free palladium-catalyzed post Ugi reaction for the synthesis of isoquinolone and pyrazole mixed pharmacophore derivatives was achieved from isocyanide and pyrazole substituted amide molecules (synthesized by using Ugi rea

Novel carboxamide compound and compositions for preventing or treating metabolic diseases comprising the same

The present invention relates to a novel carboxamide compound and a composition for preventing or treating metabolic diseases comprising the same, wherein the composition is potent and selective estrogen related receptor (Estrogen-related receptor). ERR)

Synthesis of novel 6-(1H-pyrazol-4-yl)-[1, 2, 4]triazolo[3, 4-b][1, 3, 4]thiadiazoles as potential antimicrobial agents

Background: Triazolothiadiazoles are molecules of great synthetic and pharmacological significance. They are associated with significant antimicrobial, antifungal, antibacterial, antihelmintic and anti-inflammatory activities. Method: The condensation of 5-alkyl-4-amino-3-mercapto-4H-1, 2, 4-triazoles with 3-aryl-1- phenylpyrazole-4-carboxylic acids was carried out in the presence of phosphoryl chloride and the resulting products were tested in vitro for their antibacterial potential against Bacillus subtilis (gram positive), Staphylococcus aureus (gram positive), Escherichia coli (gram negative) and Pseudomonas aeruginosa (gram negative) and further antifungal properties against Candida albicans, and Saccharomyces cervisiae. Results: A new series of 3-alkyl-6-(3-aryl-1-phenyl-1H-pyrazol-4-yl)-[1, 2, 4]triazolo[3, 4-b][1, 3, 4] thiadiazoles has been synthesized by the reaction mentioned above. One specific compound, 6-(3-(4- fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-3-methyl-[1, 2, 4]triazolo[3, 4-b][1, 3, 4]thiadiazole displayed an excellent antifungal activity against Candida albicans with a MIC value of 8 μg/ml, which is actually even better than the standard drug Amphoptericin B (MIC 10 μg/ml). Conclusion: An expeditious synthesis of several new 3-alkyl-6-(3-aryl-1-phenyl-1H-pyrazol-4-yl)- [1, 2, 4]triazolo[3, 4-b][1, 3, 4]thiadiazoles in 77-89 % yield could be performed from readily accessible starting materials, 5-alkyl-4-amino-3-mercapto-4H-1, 2, 4-triazoles and 3-aryl-1-phenylpyrazole-4- carboxylic acids. Most of the resulting compounds showed moderate to good in vitro activity against Gram-positive bacteria. The title compounds seem to be more active against fungi than bacteria.

Novel Aryl Substituted Pyrazoles as Small Molecule Inhibitors of Cytochrome P450 CYP121A1: Synthesis and Antimycobacterial Evaluation

Three series of biarylpyrazole imidazole and triazoles are described, which vary in the linker between the biaryl pyrazole and imidazole/triazole group. The imidazole and triazole series with the short -CH2- linker displayed promising antimycobacterial activity, with the imidazole-CH2- series (7) showing low MIC values (6.25-25 μg/mL), which was also influenced by lipophilicity. Extending the linker to -C(O)NH(CH2)2- resulted in a loss of antimycobacterial activity. The binding affinity of the compounds with CYP121A1 was determined by UV-visible optical titrations with KD values of 2.63, 35.6, and 290 μM, respectively, for the tightest binding compounds 7e, 8b, and 13d from their respective series. Both binding affinity assays and docking studies of the CYP121A1 inhibitors suggest type II indirect binding through interstitial water molecules, with key binding residues Thr77, Val78, Val82, Val83, Met86, Ser237, Gln385, and Arg386, comparable with the binding interactions observed with fluconazole and the natural substrate dicyclotyrosine.

Discovery of N-(benzyloxy)-1,3-diphenyl-1H-pyrazole-4-carboxamide derivatives as potential antiproliferative agents by inhibiting MEK

Mitogen activated protein kinase (MAPK) signal transduction pathway has been proved to play an important role in tumorigenesis and cancer development. MEK inhibitor has been demonstrated significant clinical benefit for blocking MAPK pathway activation and possibly could block reactivation of the MAPK pathway at the time of BRAF inhibitor resistance. Twenty N-(benzyloxy)-1,3-diphenyl-1H-pyrazole-4-carboxamide derivatives have been designed and synthesized as MEK inhibitors, and their biological activities were evaluated. Among these compounds, compound 7b showed the most potent inhibitory activity with IC50of 91?nM for MEK1 and GI50value of 0.26?μM for A549 cells. The SAR analysis and docking simulation were performed to provide crucial pharmacophore clues that could be used in further structure optimization.

Synthesis, biological evaluation and molecular docking studies of pyrazole derivatives coupling with a thiourea moiety as novel CDKs inhibitors

It was discovered that a number of cyclin dependent kinase inhibitors containing the pyrazole core structure exhibited high inhibitory potency against broad-range CDKs and corresponding anti-proliferative activities. This information guided us to design and synthesize a series of 1,3-diphenyl-N- (phenylcarbamothioyl)-1H-pyrazole-4-carboxamide derivatives (5a-10d), and evaluate their biological activities as CDKs inhibitors. Among all the synthesized compounds, compound 10b inhibited CDK2 with an IC50 value of 25 nM, counteracting tumor cell proliferation of three cancer cell lines (H460, MCF-7, A549) in the micromolar range (from 0.75 μM to 4.21 μM), In addition, flow cytometry indicated that compound 10b could induce cycle G 0/G1 phase arrest in A549 cells with a dose dependent. Taken together, compound 10b could be selected for further preclinical evaluation.

Synthesis, biological evaluation, and molecular docking studies of N,1,3-triphenyl-1H-pyrazole-4-carboxamide derivatives as anticancer agents

A series of N,1,3-triphenyl-1H-pyrazole-4-carboxamide derivatives have been designed, synthesized and evaluated for their potential antiproliferation activity and Aurora-A kinase inhibitory activity. Among all the compounds, compound 10e possessed the most potent biological activity against HCT116 and MCF-7 cell lines with IC50 values of 0.39 ± 0.06 μM and 0.46 ± 0.04 μM, respectively, which were comparable to the positive control. Compound 10e also exhibited significant Aurora-A kinase inhibitory activity (IC50 = 0.16 ± 0.03 μM). Docking simulation was performed to position compound 10e into the active site of Aurora-A kinase, in order to get the probable binding model for further study. The results of Western-blot assay demonstrated that compound 10e possessed good Aurora-A kinase inhibitory activity against HCT116. Based on the preliminary results, it is deduced that compound 10e with potent Aurora-A kinase inhibitory activity may be a potential anticancer agent.

A mild procedure for the preparation of 3-aryl-4-formylpyrazoles

A variety of 3-aryl-4-formylpyrazoles can be easily prepared in good yields from the corresponding methyl ketones, upon treatment with 2,4,6-trichloro[1,3, 5]triazine in N,N-dimethyl formamide at room temperature. This kind of pyrazole can constitute new building blocks for combinatorial chemistry.