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Volumn 18, Issue 14, 2008, Pages 3882-3886

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-carboxy lic acid piperidin-1-ylamide (SR141716) a potent CB1 receptor antagonist

Author keywords

CB1 receptor antagonist; hCB1(cAMP)assay; Mouse vas defense assay; PLP (piece wise linear potential) scores; Sulfonamide derivative

Indexed keywords

2,3 DIHYDRO 5 METHYL 3 (MORPHOLINOMETHYL) 6 (1 NAPHTHOYL)PYRROLO[1,2,3 DE][1,4]BENZOXAZINE; 5 (4 CHLOROPHENYL) 1 (2,4 DICHLOROPHENYL) 4 METHYL 1H PYRAZOLE 3 CARBOXYLIC ACID PIPERIDIN 1 YLAMIDE SULFONAMIDE DERIVATIVE; CANNABINOID 1 RECEPTOR; CANNABINOID 1 RECEPTOR ANTAGONIST; DIMETHYL SULFOXIDE; FORSKOLIN; RIMONABANT; SULFONAMIDE;

EID: 48949115102     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.06.045     Document Type: Article
Times cited : (9)

References (39)
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    • note
    • 2O 2.54. Isometric contractions were evoked by stimulation with 0.9 s trains of three pulses of 110% maximal voltage (train frequency 0.1 Hz; pulse duration 0.9 ms) through a platinum electrode attached to the upper end and a stainless steel electrode attached to the lower end of each bath. Contractile response was recorded using Spel Isosys computer aided data acquisition system (Experimetria, Hungary). Concentration response curve of WIN-55212-2 was taken in presence of control, 1, 2, and 3 using three different tissue preparations of mouse vas deferens. WIN-55212-2 was dissolved in 5% v/v Tween 80 in water, and test compounds were dissolved in 1% v/v DMSO and 5% v/v Tween 80 in water. Further dilutions were achieved by adding water both to the stock solution of WIN-55212-2 and test compounds.
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    • note
    • Procedures for synthesis of compounds 5, 7, 8, 2, and 3: Synthesis of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbony l azide 5: The 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxy lic acid 4 (1.2 g, 3.14 mmol) was taken in dichloromethane (12 mL) to which oxalyl chloride (0.35 mL, 4.08 mmol) was added drop wise at -20 °C. The solution was stirred at 0-5 °C for 30 min and stirred at 25-27 °C for a period of 1 h. The progress of the reaction was monitored by TLC using 5% methanol in chloroform as a mobile phase. The solvents were evaporated on a rotatory evaporator under reduced pressure to afford an oil (1.25 g, 100%), which was dissolved in dichloromethane (14.5 mL) and to this tetrabutylammonium bromide (3.0 mg, 9.0 mmol) was added followed by addition of 35% aqueous sodium azide (1 mL) at 0 °C. The resulting mixture was stirred at 0-5 °C for 2 h. The progress of the reaction was monitored by TLC using 40% EtOAc in petroleum ether as a mobile phase.


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