Chiral resolution of alpha,alpha'-bis[3-(N,N-diethylcarbamoyl)piperidino]-p-xylene, a novel antiplatelet compound.
alpha,alpha'-Bis[3-(N,N-diethylcarbamoyl)piperidino]-p-xylene dihydrobromide, a novel antiplatelet agent, was resolved into three isomers A, B, and C, on a chiral alpha 1-acid glycoprotein analytical column using a mobile phase of 0.025 M phosphate buffer containing 0.025 M tetrabutylammonium hydrogen sulfate, at a pH of 6.5. The effect of molarity, temperature, pH, flow rate, and organic modifiers on the enantioselectivity was examined. Based on circular dichroic spectra at 220 nm, A and C appear to be the (-)- and (+)-enantiomers, respectively, and B the meso diastereomer. Attempts at resolution using Pirkle type columns gave unsatisfactory results. It appears that both hydrophobic and polar interactions between the compound and the stationary phase are important determinants of resolution.
Gollamudi
R
R
Department of Medicinal Chemistry, College of Pharmacy, University of Tennessee-Memphis 38163.
Feng
Z X
ZX
D002851:Chromatography, High Pressure Liquid; D009557:Nipecotic Acids / Q000737:chemistry*; D009994:Osmolar Concentration; D010975:Platelet Aggregation Inhibitors / Q000737:chemistry*; D000644:Quaternary Ammonium Compounds / Q000494:pharmacology; D013237:Stereoisomerism
D009557:Nipecotic Acids; D010975:Platelet Aggregation Inhibitors; D000644:Quaternary Ammonium Compounds; C043099:alpha, alpha'-bis(3-(N,N-diethylcarbamoyl)piperidino)-4-xylene; C009405:tetrabutylammonium