Journal of Medicinal Chemistry p. 1406 - 1413 (1990)
Update date:2022-08-04
Topics:
Kato
Morie
Hino
Kon
Naruto
Yoshida
Karasawa
Matsumoto
With the purpose of obtaining more potent and selective gastric prokinetic agents than metoclopramide (1), a new series of N-[(2-morpholinyl)alkyl]benzamides (17-52) were synthesized and their gastric prokinetic activity was evaluated by determining effect on the gastric emptying of phenol red semisolid meal and of resin pellets solid meal in rats and mice. The morpholinyl moiety was newly designed after consideration of the side-chain structure of cisapride (2) and produced the desired activity when coupled with the 4-amino-5-chloro-2-methoxybenzoyl group of both metoclopramide and cisapride. Modification of the substituents of the benzoyl group markedly influenced the activity. In particular, 4-amino-N-[benzyl-2-morpholinyl)methyl]-5-chloro-2-methoxybenzamide (17) and the 4-(dimethylamino) and 2-ethoxy analogues (25 and 29) or 17 showed potent and selective gastric prokinetic activity along with a weak dopamine D2 receptor antagonistic activity.
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Doi:10.1016/S0040-4039(01)80576-1
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