1199215-68-3

Usage

Usage in organic synthesis

Building block for pharmaceuticals and bioactive molecules 1H-pyrazole-5-carboxylic acid, 3-(1,1-dimethylethyl)-1-phe is commonly used as a building block in the synthesis of various pharmaceuticals and bioactive molecules due to its unique structure and reactivity.

Contains 1H-pyrazole-5-carboxylic acid core

Importance for peptide synthesis The presence of the 1H-pyrazole-5-carboxylic acid core makes the compound an important intermediate for the synthesis of peptides and peptidomimetic compounds.

Tert-butyl-protected phenylalanine residue

Enhances stability and allows selective deprotection The tert-butyl protecting group enhances the stability of the compound and enables selective deprotection under appropriate reaction conditions, which is crucial for the synthesis of complex peptide and peptidomimetic structures.

Upstream product

• 13395-36-3 ethyl trimethylacetopyruvate 
• 100-63-0 phenylhydrazine 
• 75-97-8 3,3-dimethyl-butan-2-one 

Downstream Products

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

Relevant academic research and scientific papers

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.

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.