797053-26-0

Upstream product

• 5446-18-4 2,4-dichlorophenyl hydrazine hydrochloride 
• 58582-97-1 ethyl 1-(4'-chlorophenyl)-3-(dimethylamino)-prop-2-enone-2-carboxylate 

Downstream Products

• 1103532-82-6 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carboxylic acid 
• 797053-60-2 [5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-1H-pyrazol-4-yl]-phenyl-methanol 
• 797053-48-6 5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-1H-pyrazole-4-carbaldehyde 
• 797053-37-3 [5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-1H-pyrazol-4-yl]-methanol 

Relevant academic research and scientific papers

Rational design, synthesis and biological evaluation of new 1,5-diarylpyrazole derivatives as CB1 receptor antagonists, structurally related to rimonabant

Among cannabinoid type-1 (CB1) receptor antagonists, those developed around the 1,5-diarylpyrazole scaffold of rimonabant (Acomplia) are the most extensively investigated. In recent years, many SAR and QSAR reports on this topic have been published, focusing on the substitution and orientation of the N1 and C5 aryl functionalities and on the substituents at the 3-carboxamide position. In this context, the purpose of our study was to design and synthesize a set of 1-(2,4-dichlorophenyl)-5-arylpyrazoles strictly related to rimonabant, but with the hydrazide/amide group shifted from position 3 to position 4 of the pyrazole scaffold. The synthesized compounds were evaluated in vitro for their affinity on human CB1 and CB2 (cannabinoid type-2) receptors. Computational studies, performed both in the design step and after biological assays, contributed to rationalize the obtained results in terms of specific molecular interactions between antagonists and the human CB1 receptor.

Synthesis, antimicrobial activity and molecular modeling studies of halogenated 4-[1H-imidazol-1-yl(phenyl)methyl]-1,5-diphenyl-1H-pyrazoles

Halogenated diphenylpyrazole analogues of bifonazole were prepared and their microbiological properties were investigated. During the course of our studies in the azole antifungals area, we synthesized a number of 1,5-disubstituted 4-[1H-imidazol-1-yl(phenyl)methyl]-1H-pyrazoles, analogues of bifonazole. 1,5-Diphenyl-1H-pyrazole 3 showed weak antimycotic and antibacterial activities in vitro against Candida albicans, Cryptococcus neoformans and Staphylococcus aureus. In order to increase these properties, given that the halo substitution was found to be capable of enhancing antifungal effects, we prepared a series of fluoro and chloro derivatives of 3. The microbiological evaluation carried out on newly synthesized compounds included in vitro assays for antifungal, antibacterial and antimycobacterial activities. Among the tested compounds, some dichloro and trichloro-derivatives showed interesting antimicrobial properties. In particular, compounds 10j,k,l produced inhibitory effects against pathogen representatives of yeast (C. albicans, C. neoformans) and Gram positive bacteria (S. aureus) similar or superior to those of bifonazole. In addition, their activity against Mycobacterium tuberculosis was superior to that of clotrimazole and econazole, which were used as reference drugs. The replacement, in these compounds, of chlorine with fluorine atoms led to inactive derivatives.Docking studies were carried out on the most active compounds, in order to rationalize the pharmacological results.