The synthesis of a series of 1-aralkyl-4-ureidopiperidines is reported. These compounds are related to the benzamidopiperidines exemplified by indoramin. Some of the ureidopiperidines are more potent antihypertensive agents than their benzamidopiperidine counterparts. Two examples, 1-(2-thenoyl)-3-[1-[2-(3-indolyl)ethyl]piperid-4-yl]urea and 1-(2-thenoyl)-3-[1-[4-(4-fluorophenyl)-4-oxobutyl]piperid-4-yl]urea (19 and 58), emerged as the most potent antihypertensive agents in this series.
°All compounds exhibited IR and NMR spectra consistent with the assigned structure.b There were four rats per group in each experiment. c Yield of analytically pure material; yields were not optimized. d C, H, and N analyses were within ±0.4% of theoretical values for the formulas given. ® Means ± SE; all results were analyzed for statistically significant differences from control values using analysis of variance; nonsignificant values (p > 0.05) are indicated by an asterisk, f Decomposition. g Toxic at 50 mg/kg.
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