Facile synthesis, ex-vivo and in vitro screening of 3-sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide (SR141716) a potent CB1 receptor antagonist

Bioorganic & Medicinal Chemistry Letters
2008.0

Abstract

Facile synthesis of biaryl pyrazole sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide (SR141716, 1) and an investigation of the effect of replacement of the -CO group in the compound 1 by the -SO(2) group in the aminopiperidine region is reported. Primary ex-vivo pharmacological testing and in vitro screening of sulfonamide derivative 2 showed the loss of CB1 receptor antagonism.

Knowledge Graph

Similar Paper

Facile synthesis, ex-vivo and in vitro screening of 3-sulfonamide derivative of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide (SR141716) a potent CB1 receptor antagonist
Bioorganic & Medicinal Chemistry Letters 2008.0
Biarylpyrazole Inverse Agonists at the Cannabinoid CB1 Receptor:  Importance of the C-3 Carboxamide Oxygen/Lysine3.28(192) Interaction
Journal of Medicinal Chemistry 2006.0
Bioisosteric replacement of dihydropyrazole of 4S-(−)-3-(4-chlorophenyl)-N-methyl-N′-[(4-chlorophenyl)-sulfonyl]-4-phenyl-4,5-dihydro-1H-pyrazole-1-caboxamidine (SLV-319) a potent CB1 receptor antagonist by imidazole and oxazole
Bioorganic & Medicinal Chemistry Letters 2008.0
Novel sulfenamides and sulfonamides based on pyridazinone and pyridazine scaffolds as CB 1 receptor ligand antagonists
Bioorganic & Medicinal Chemistry 2018.0
Arylsulfonamides as a new class of cannabinoid CB1 receptor ligands: Identification of a lead and initial SAR studies
Bioorganic & Medicinal Chemistry Letters 2007.0
Two distinct classes of novel pyrazolinecarboxamides as potent cannabinoid CB1 receptor agonists
Bioorganic & Medicinal Chemistry Letters 2010.0
Pyrazole antagonists of the CB1 receptor with reduced brain penetration
Bioorganic & Medicinal Chemistry 2016.0
Discovery of 1,1-dioxo-1,2,6-thiadiazine-5-carboxamide derivatives as cannabinoid-like molecules with agonist and antagonist activity
Bioorganic & Medicinal Chemistry 2007.0
Novel pyrazole derivatives as neutral CB 1 antagonists with significant activity towards food intake
European Journal of Medicinal Chemistry 2013.0
Synthesis, molecular modeling and SAR study of novel pyrazolo[5,1- f ][1,6]naphthyridines as CB 2 receptor antagonists/inverse agonists
Bioorganic & Medicinal Chemistry 2016.0