Synthesis and biological activity of 4-amino-5-chloro-2-ethoxy-3-hydroxybenzamides, metabolites of a new gastroprokinetic agent, mosapride.
摘要：
To confirm the proposed structures of the minor metabolites of a potential gastroprokinetic agent, mosapride, 4-amino-5-chloro-2-ethoxy-3-hydroxy-N-(2-morpholinylmethyl)benzamide (3) and the N-(5-oxo-2-morpholinyl)-methyl analogue 4 were prepared. As the common intermediate, 2-ethoxy-3-hydroxy-4-nitrobenzoic acid (15) was prepared via the regioselective ethylation of 2,3-dihydroxybenzaldehyde (10) and subsequent nitration of the resultant 2-ethoxy-3-hydroxybenzaldehyde (11). The key intermediate 15 was converted into the benzamides 3 and 4. After enzymatic treatment of the isolated metabolites, their structures were identified by comparison with the synthetic compounds. Serotonin-4 receptor binding affinity of these metabolites was found to be lower than that of mosapride.
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关键词：
mosapride gastroprokinetic activity serotonin-4 receptor agonist 4-amino-5-chloro-2-ethoxy-N-{[4-(4-fluorobenzyl)-2-morpholinyl]methyl}be nzamide
DOI：
10.1002/chin.199711129
被引量：
年份：
1996
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