827614-69-7

Usage

Uses

Used in Organic Synthesis:
1-Propyl-1H-pyrazole-4-boronic acid pinacol ester is used as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds, facilitating the synthesis of complex organic molecules.
Used in Pharmaceutical Development:
1-Propyl-1H-pyrazole-4-boronic acid pinacol ester is used as a building block in the development of pharmaceuticals, leveraging its unique chemical properties to create novel therapeutic agents.
Used in Agrochemical Development:
1-Propyl-1H-pyrazole-4-boronic acid pinacol ester is used as a precursor in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural products.
Used in Research Studies:
1-Propyl-1H-pyrazole-4-boronic acid pinacol ester is used as a research tool in various scientific studies, exploring its potential applications and expanding the understanding of its chemical behavior and reactivity.

InChI:InChI=1/C12H21BN2O2/c1-6-7-15-9-10(8-14-15)13-16-11(2,3)12(4,5)17-13/h8-9H,6-7H2,1-5H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 847818-57-9 (1-propyl-1H-pyrazol-4-yl)boronic acid 
• 269410-08-4 pyrazole-4-boronic acid pinacol ester 
• 107-08-4 1-iodo-propane 
• 141302-33-2 4-bromo-1-propyl-1H-pyrazole 

Downstream Products

• 1094567-91-5 C₃₁H₃₂F₃N₇O 
• 1329989-31-2 C₃₁H₂₉F₃N₄O₄ 
• 1329991-33-4 C₃₈H₃₅F₃N₄O₄ 
• 1201641-12-4 tert-butyl 3-(3-(1-propyl-1H-pyrazol-4-yl)phenethoxy)propanoate 

Relevant academic research and scientific papers

Development of novel amide–derivatized 2,4-bispyridyl thiophenes as highly potent and selective Dyrk1A inhibitors. Part II: Identification of the cyclopropylamide moiety as a key modification

Dual-specificity tyrosine phosphorylation-regulated kinase 1A (Dyrk1A) is a potential target in Alzheimer's disease (AD) because of the established correlation between its over-expression and generation of neurofibrillary tangles (NFT) as well as the accumulation of amyloid plaques. However, the use of Dyrk1A inhibitors requires a high degree of selectivity over closely related kinases. In addition, the physicochemical properties of the Dyrk1A inhibitors need to be controlled to enable CNS permeability. In the present study, we optimized our previously published 2,4-bispyridyl thiophene class of Dyrk1A inhibitors by the synthesis of a small library of amide derivatives, carrying alkyl, cycloalkyl, as well as acidic and basic residues. Among this library, the cyclopropylamido modification (compound 4b) was identified as being highly beneficial for several crucial properties. 4b displayed high potency and selectivity against Dyrk1A over closely related kinases in cell-free assays (IC50: Dyrk1A = 3.2 nM; Dyrk1B = 72.9 nM and Clk1 = 270 nM) and inhibited the Dyrk1A activity in HeLa cells with high efficacy (IC50: 43 nM), while no significant cytotoxicity was observed. In addition, the cyclopropylamido group conferred high metabolic stability and maintained the calculated physicochemical properties in a range compatible with a potential CNS activity. Thus, based on its favourable properties, 4b can be considered as a candidate for further in vivo testing in animal models of AD.

Synthesis of pinacol esters of 1-alkyl-1H-pyrazol-5-yl- and 1-alkyl-1H-pyrazol-4-ylboronic acids

Starting from 1H-pyrazol, a wide number of 1-alkyl-1H-pyrazol-4-yl and 1-alkyl-1H-pyrazol-5-ylboronic acids and their pinacol esters were synthesized and characterized. The key step in the described methodology is the regioselective lithiation of the pyrazole ring. The synthesized pinacolates are stable under prolonged storage and can be used as convenient reagents in organic synthesis.