Hypotensive and antinociceptive effects of ether-linked and relatively non-pungent analogues of N-nonanoyl vanillylamide

Add time:07/12/2019    Source:sciencedirect.com

N-nonanoyl vanillylamide (1) is a synthetic substitute of capsaicin (2), a pungent principle in red pepper. 1 was reacted with succinic anhydride, 3-chloro-1,2-propanediol, sodium chloroacetate, and 2-chloroethanol to furnish N-nonanoyl vanillylamide-4-succinyl ester (3), N-nonanoyl vanillylamide-4-glyceryl ether (4), sodium N-nonanoyl vanillylamide-4-O-acetate (5) and N-nonanoyl vanillylamide-4-glycol ether (6), respectively. A 3,4-methylenedioxy derivative of 1, N-nonanoyl piperonylamide (7), was synthesized from piperonylamine HCl and nonanoyl chloride. The ether analogues 4–6 all demonstrated marked antinociceptive and hypotensive effects without producing any overt irritation. In addition, these compounds revealed no untoward vagus reflex or transient hypertensive effect as previously found in 1 or 2.

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