Add time:08/29/2019         Source:sciencedirect.com

Summary4-Amino-N-[(4-benzyl-2-morpholinyl)methyl]-5-chloro-2-methoxybenzamide 1a and its 2-ethoxy analogue 1b show a potent gastroprokinetic activity. To examine the effect of reversal of the amide linkage of 1a and 1b, N-(4-amino-5-chloro-2-methoxyphenyl)-4-benzyl-2-morpholineacetamide and related compounds (2 and 8–13) were prepared and evaluated for gastroprokinetic activity by determining their effects on gastric emptying of a phenol red semisolid meal and a serotonin-4 receptor binding assay. Reversal of the amide bond resulted in a fall in activity; the amide bond of the 2-morpholinyl benzamides is essential for a potent gastroprokinetic activity. Molecular superimposition of 2c upon 1b using computer graphics suggested that the location of the morpholine ring and N-benzyl group is crucial for the activity.

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