741287-00-3

Upstream product

• 100-63-0 phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 
• 93-55-0 1-phenyl-propan-1-one 
• 95-92-1 oxalic acid diethyl ester 
• 1105739-75-0 (Z)-ethyl 2-hydroxy-3-methyl-4-oxo-4-phenylbut-2-enoate 

Downstream Products

• 112009-32-2 4-methyl-1,5-diphenyl-1H-pyrazole-3-carboxylic acid 
• 1428261-51-1 C₃₅H₄₉N₃O 
• 1428261-52-2 C₃₃H₄₇N₃O 
• 1428261-53-3 4-methyl-1,5-diphenyl-N-(1-piperidinyl)-1H-pyrazole-3-carboxamide 

Relevant academic research and scientific papers

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

Novel antiobesity agents: Synthesis and pharmacological evaluation of analogues of Rimonabant and of LH21

Searching for novel antiobesity agents, a series of cannabinoid LH21 and of Rimonabant-fatty acid amide analogues have been prepared. Synthesis of pyrazoles 2a-2c was achieved by a two steps simple methodology via α,β-unsaturated ketones. Carboxamides 8a-8h were obtained in good yields from esters 7a-7c by a one-pot procedure which takes place under mild conditions. New compounds have been evaluated in vivo as anorectic agents. Some of them showed interesting properties reducing food intake in rats by a mechanism which does not involve the endocannabinoid system.

'One-pot' synthesis of 4-substituted 1,5-diaryl-1H-pyrazole-3-carboxylates via lithium tert-butoxide-mediated sterically hindered Claisen condensation and Knorr reaction

A concise 'one-pot' synthesis of a variety of 4-substituted 1,5-diaryl-1H-pyrazole-3-carboxylates has been developed in moderate to good yields with excellent regioselectivity. Less cost lithium tert-butoxide has been identified as a base for sterically hindered Claisen condensation to efficiently generate the labile 3-substituted 4-aryl-2,4-diketoesters. Furthermore, extensive studies lead to a 'one-pot' process by combination of the Claisen condensation and the Knorr reaction for the synthesis of highly valuable 4-substituted 1,5-diaryl-1H-pyrazole-3-carboxylates.

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.

"One-poto" synthesis of 4-substituted 1,5-diaryl-1H-pyrazole-3- carboxylic acids via a MeONa/LiCl-mediated sterically hindered claisen condensation-Knorr reaction-hydrolysis sequence

A "one-poto" synthesis of 4-substituted 1,5-diaryl-1H-pyrazole-3- carboxylic acids was first reported in moderate to good yields. This concise procedure, featuring efficiency and green chemistry, was composed of MeONa/LiCl-mediated sterically hindered Claisen condensation, Knorr reaction and hydrolysis. Georg Thieme Verlag KG · Stuttgart · New York.

The structure of two pyrazole esters related to Rimonabant

Two 1,5-diarylpyrazoles related to the antiobesity agent Rimonabant have been synthesized and their structure determined by X-ray crystallography. Compound 2, 1-(2,4-dichlorophenyl)-5-(4-chlorophenyl)-4-methyl-1H-pyrazole-3-carboxy late, forms strange cry

PYRAZOLE DERIVATIVE

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