221385-23-5

Basic information

• Product Name: 1-(2,4-Dichlorophenyl)-4-Methyl-5-phenyl-1H-pyrazole-3-carboxylic Acid Ethyl Ester
• Synonyms: 1-(2,4-Dichlorophenyl)-4-Methyl-5-phenyl-1H-pyrazole-3-carboxylic Acid Ethyl Ester
• CAS NO: 221385-23-5
• Molecular Formula: C₁₉H₁₆Cl₂N₂O₂
• Molecular Weight: 375.24854
• Product Categories: Aromatics, Heterocycles, Intermediates, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 221385-23-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 80-82 °C
• Boiling Point: 501.3±50.0 °C(Predicted)
• Appearance: /
• Density: 1.29±0.1 g/cm3(Predicted)
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: -2.25±0.10(Predicted)
• CAS DataBase Reference: 1-(2,4-Dichlorophenyl)-4-Methyl-5-phenyl-1H-pyrazole-3-carboxylic Acid Ethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-Dichlorophenyl)-4-Methyl-5-phenyl-1H-pyrazole-3-carboxylic Acid Ethyl Ester(221385-23-5)
• EPA Substance Registry System: 1-(2,4-Dichlorophenyl)-4-Methyl-5-phenyl-1H-pyrazole-3-carboxylic Acid Ethyl Ester(221385-23-5)

Safety Data

• Hazardous Substances Data: 221385-23-5(Hazardous Substances Data)

Usage

Description

1-(2,4-dichlorophenyl)-4-methyl-5-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester is a complex organic compound characterized by its beige solid appearance. It is a key intermediate in the synthesis of biarylpyrazole-based derivatives, which have significant applications in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
1-(2,4-dichlorophenyl)-4-methyl-5-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester is used as a key intermediate for the preparation of biarylpyrazole-based derivatives. These derivatives are known as cannabinoid CB1 receptor antagonists, which have potential applications in the treatment of various disorders related to the central nervous system, such as obesity, metabolic syndrome, and neurodegenerative diseases.
1-(2,4-dichlorophenyl)-4-methyl-5-phenyl-1H-pyrazole-3-carboxylic acid ethyl ester's unique structure allows it to effectively modulate the CB1 receptor, offering a promising avenue for the development of novel therapeutic agents. Its use in the pharmaceutical industry is primarily driven by the need for innovative treatments that target the endocannabinoid system, which plays a crucial role in regulating various physiological processes.

Upstream product

• 93-55-0 1-phenyl-propan-1-one 
• 5446-18-4 2,4-dichlorophenyl hydrazine hydrochloride 
• 95-92-1 oxalic acid diethyl ester 
• 13123-92-7 (2,4-dichlorophenyl)hydrazine 
• 221385-22-4 ethyl 3-methyl-2,4-dioxo-4-phenylbutanoate lithium salt 

Downstream Products

• 221385-26-8 1-(2,4-dichloro-phenyl)-4-methyl-5-(2-nitro-phenyl)-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide 
• 221385-25-7 1-(2,4-dichloro-phenyl)-4-methyl-5-(4-nitro-phenyl)-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide 
• 221385-47-3 1-(2,4-dichlorophenyl)-4-methyl-5-phenyl-1H-pyrazole-3-carboxylic acid 
• 183232-66-8 1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-(1-piperidinyl)-1H-pyrazole-3-carboxamide 
• 221385-48-4 1-(2,4-dichloro-phenyl)-4-methyl-5-phenyl-1H-pyrazole-3-carbonyl chloride 
• 221385-29-1 5-(2-amino-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide 
• 221385-28-0 5-(4-amino-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide 

Relevant articles and documents

1,5-Diarylpyrazole and vanillin hybrids: Synthesis, biological activity and DFT studies

Herein, we report the design and synthesis of 13 diarylpyrazole hybrids with vanillin constructed as dual compounds against oxidative stress and diabetes. Compounds were tested in two different antioxidant assays. It was found that all compounds showed an

Synthesis, hypoglycemic activity and molecular modeling studies of pyrazole-3-carbohydrazides designed by a CoMFA model

Diabetes and obesity are two universal health problems that constitute a research objective of several groups due to the lack of efficient and safe drug treatment. In this sense, cannabinoid receptor 1 (CB1) has attracted interest because of its role in food intake and metabolic balance, two targets in the control of metabolic syndrome. In this work, novel 1,5-diaryl pyrazole derivatives were synthesized in accordance with the pKi prediction of a previously reported CoMFA model by our group. To further investigate the biological activity of these compounds in metabolic disorders, their hypoglycemic activity in an in vivo model was tested. Interestingly, a high degree of correlation was observed between the predicted pKi and hypoglycemic effect 7 h after administration. Compounds 4, 9 and 13 showed the most significant plasma glucose reduction with decreases of 60%, 64% and 60% respectively. This result not only surpasses the activity of the lead rimonabant, but also that of the reference drug glibenclamide. Moreover, PASS prediction and molecular docking in an excellent validated homology model of CB1 suggest that these compounds would probably act as CB1 antagonists/inverse agonists and therefore, anti-obesity agents. The ligand-receptor complexes demonstrate that 1,5-diaryl pyrazole derivatives bind to the proposed binding site where a hydrophobic moiety interacts with the phenyl rings in the pyrazole nucleus and Lys192 forms a hydrogen bond with the oxygen of the carbonyl group. Dynamics simulations were also carried out to study the stability of the ligand-receptor complexes where the most active compounds showed smaller ΔG values and more hydrogen bonds throughout the simulation. These compounds are considered useful leads for further optimization in the treatment of such metabolic illnesses.

Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists

As a potent, specific antagonist for the brain cannabinoid receptor (CB1), the biarylpyrazole N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4- dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (SR141716A; 1) was the lead compound for initiating studies desi