93045-47-7

Usage

Uses

Used in Medicinal Chemistry:
3-(tert-butyl)-1-phenyl-1H-pyrazole-5-carboxylic acid is used as a building block in the synthesis of pharmaceuticals for its potential to exhibit biological activity. Its structural components, including the tert-butyl, phenyl, and carboxylic acid groups, may contribute to its interaction with biological targets, making it a valuable component in the development of new drugs.
Used in Drug Development:
In the pharmaceutical industry, 3-(tert-butyl)-1-phenyl-1H-pyrazole-5-carboxylic acid is utilized as a precursor in the creation of novel drug candidates. Its unique molecular structure allows for the exploration of various chemical modifications, which can lead to the discovery of compounds with improved pharmacological properties, such as enhanced potency, selectivity, and reduced side effects.
Used in Organic Synthesis:
3-(tert-butyl)-1-phenyl-1H-pyrazole-5-carboxylic acid serves as a versatile intermediate in organic synthesis across different chemical industries. Its functional groups can be further modified or used to construct more complex molecules, which can find applications in various sectors, including materials science, agrochemicals, and specialty chemicals.

InChI:InChI=1/C14H16N2O2/c1-14(2,3)12-9-11(13(17)18)16(15-12)10-7-5-4-6-8-10/h4-9H,1-3H3,(H,17,18)

Upstream product

• 75-97-8 3,3-dimethyl-butan-2-one 
• 1199215-68-3 C₁₆H₂₀N₂O₂ 
• 13395-36-3 ethyl trimethylacetopyruvate 

Downstream Products

• 956489-20-6 3-tert-butyl-1-phenyl-pyrazole-5-carbonyl chloride 

Relevant academic research and scientific papers

Design, synthesis and biological activity of novel substituted pyrazole amide derivatives targeting EcR/USP receptor

In order to discover highly active ecdysone analogs, a series of new substituted pyrazole amide derivatives were obtained using structure-guided optimization method and further screened for their insecticidal activities, in the basis of the core structures of the two active compounds N-(3-methoxyphenyl)-3-(tert-butyl)-1-phenyl-1H-pyrazole-5-carboxamide (6e) and N-(4-(tert-butyl)phenyl)-3-(tert-butyl)-1-phenyl-1H-pyrazole-5-carboxamide (6i), previously presented by us. The chemical structures of the title compounds were identified by spectral analyses. The preliminary bioassay results indicated that one among the synthesized pyrazole derivatives, compound 34, endowed with good activity against Mythimna Separata at 10 mg/L, which was equal to that displayed by the positive control tebufenozide. In addition, examples of molecular docking and molecular dynamics studies demonstrated that 34 may be the potential inhibitor to EcR and its docking conformation was similar to that of tebufenozide. In addition, increasing the hydrophobic effect and considering the suitable bulk effect on pyrazole ring are beneficial to the inhibiting activity to EcR and activity in vivo.

Target-based design, synthesis and biological activity of new pyrazole amide derivatives

Based on the similarities in the conformation of VS008 (N-(4-methylphenyl)-3-(tert-butyl)-1-(phenylmethyl)-1H-pyrazole-5-carboxamide) and BYIO6830 (N′-(3,5-dimethylbenzoyl)-N′-tert-butyl-5-methyl-2,3-dihydro-1,4-benzodioxine-6-carbohydrazide) bound to the active site of the EcR subunit of the ecdysone receptor (EcR)-ultraspiracle protein (USP) heterodimeric receptor, a series of new pyrazole amide derivatives were designed and synthesized. Their structures were confirmed by IR, 1HNMR, 13C NMR and elemental analysis. Results from a preliminary bioassay revealed that two of the pyrazole derivatives exhibited promising insecticidal activity. Specifically, compounds 6e and 6i exhibited good activity against Helicoverpa armigera (cotton bollworm) at low concentration. Symptoms displayed by tebufenozide-treated H. armigera were identical with those displayed by its treated counterpart. 6i showed the same poisoning symptoms as those of tebufenozide. In addition, results from molecular docking result indicated that the binding modes of 6e and 6i at the active site of the EcR subunit of the heterodimeric receptor were similar to that of the bound tebufenozide.