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.
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.
Kumar Srivastava
Brijesh
B
Department of Medicinal Chemistry, Zydus Research Centre, Cadila Healthcare Ltd., Sarkhej-Bavla N. H.8A, Moraiya, Ahmedabad 382210, India. brijeshsrivastava@zyduscadila.com
Soni
Rina
R
Patel
Jayendra Z
JZ
Jha
Satadru
S
Shedage
Sandeep A
SA
Gandhi
Neha
N
Sairam
Kalapatapu V V M
KV
Pawar
Vishwanath
V
Sadhwani
Nisha
N
Mitra
Prasenjit
P
Jain
Mukul R
MR
Patel
Pankaj R
PR
D000818:Animals; D002626:Chemistry, Pharmaceutical / Q000379:methods; D015195:Drug Design; D020128:Inhibitory Concentration 50; D051379:Mice; D008956:Models, Chemical; D008968:Molecular Conformation; D010880:Piperidines / Q000737:chemistry / Q000494:pharmacology*; D011720:Pyrazoles / Q000494:pharmacology*; D043884:Receptor, Cannabinoid, CB1 / Q000037:antagonists & inhibitors*; D000077285:Rimonabant; D013449:Sulfonamides / Q000737:chemistry*
D010880:Piperidines; D011720:Pyrazoles; D043884:Receptor, Cannabinoid, CB1; D013449:Sulfonamides; D000077285:Rimonabant