595610-47-2

Basic information

• Product Name: 1H-Pyrazole-3-carboxylic acid, 5-(2-phenylethyl)-, ethyl ester
• Synonyms: 1H-Pyrazole-3-carboxylic acid, 5-(2-phenylethyl)-, ethyl ester;Ethyl 5-phenethyl-1H-pyrazole-3-carboxylate
• CAS NO: 595610-47-2
• Molecular Formula: C₁₄H₁₆N₂O₂
• Molecular Weight: 244.28904
• Mol File: 595610-47-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 406.2±33.0 °C(Predicted)
• Appearance: /
• Density: 1.169±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 11.60±0.10(Predicted)
• CAS DataBase Reference: 1H-Pyrazole-3-carboxylic acid, 5-(2-phenylethyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazole-3-carboxylic acid, 5-(2-phenylethyl)-, ethyl ester(595610-47-2)
• EPA Substance Registry System: 1H-Pyrazole-3-carboxylic acid, 5-(2-phenylethyl)-, ethyl ester(595610-47-2)

Safety Data

• Hazardous Substances Data: 595610-47-2(Hazardous Substances Data)

Usage

Class

pyrazole derivatives

Common uses

organic synthesis, pharmaceutical research

Molecular weight

256.3 g/mol

Appearance

colorless to pale yellow liquid

Boiling point

175-176 °C

Primary applications

intermediate in the production of pharmaceuticals and agrochemicals

Upstream product

• 100884-20-6 2,4-dioxo-6-phenyl-hexanoic acid ethyl ester 
• 2550-26-7 4-Phenyl-2-butanone 

Downstream Products

• 595610-56-3 5-phenethyl-1H-pyrazole-3-carboxylic acid 

Relevant articles and documents

AUTOTAXIN INHIBITORS

The present invention relates to compounds of formula (I): wherein R1, R2, R3, R4a, R4b, R4C, R4d, L, A, Q, W and HET are each as defined herein. The compounds of the present inv

Pyrazole derivatives as partial agonists for the nicotinic acid receptor

Nicotinic acid as a hypolipidemic agent appears unique due to its potential to increase HDL cholesterol levels to a greater extent than other drugs. However, it has some side effects, among which severe skin flushing is the most frequent and often limits patients' compliance. In a search for novel agonists for the recently identified and cloned G protein-coupled nicotinic acid receptor, we synthesized a series of substituted pyrazole-3-carboxylic acids that proved to have substantial affinity for this receptor. The affinities were measured by inhibition of [3H] nicotinic acid binding to rat spleen membranes. Potencies and intrinsic activities relative to nicotinic acid were determined by their effects on [35S]GTPγS binding to rat adipocyte and spleen membranes. Interestingly, most compounds were partial agonists. In particular, 2-diazabicyclo-[3,3,O 4,8]octa-3,8-diene-3-carboxylic acid (4c) and 5-propylpyrazole-3-carboxylic acid (4f) proved active with Ki values of approximately 0.15 μM and EC50 values of approximately 6 μM, while their intrinsic activity was only ～50% when compared to nicotinic acid. Even slightly more active was 5-butylpyrazole-3-carboxylic acid (4g) with a Ki value of 0.072 μM, an EC50 value of 4.12 μM, and a relative intrinsic activity of 75%. Of the aralkyl derivatives, 4q (5-(3-chlorobenzyl)pyrazole-3-carboxylic acid) was the most active with a relatively low intrinsic activity of 39%. Partial agonism of the pyrazole derivatives was confirmed by inhibition of G protein activation in response to nicotinic acid by these compounds. The pyrazoles both inhibited the maximum effect elicited by 100 μM nicotinic acid and concentration dependently shifted nicotinic acid concentration-response curves to the right, pointing to a competive mechanism of action.