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- W1990383544 abstract "Aseries of novel benzimidazole-2-carboxylic acid amides and esters with a quinuclidine or a tropane moiety were synthesized and evaluated for in vitro affinity for the 5-HT3, 5-HT4 and D2 receptors. Compounds 15a, 13j and 13h exhibited affinity for the 5-HT3 receptor (Ki = 20.2, 18.4 and 12.7 nM, respectively) and no significant affinity for both 5-HT4 and D2 receptors. The amide-ester replacement did not induce significant changes in the affinity profile. The enantioselectivity for the 5-HT3 receptor was reversed with regard to the zacopride pattern and the (R)-enantiomer 13c showed higher affinity (Ki = 56.4 nM) than the (S)-enantiomer 13d (Ki = 242.3 nM). An increment of the steric hindrance around the nitrogen atom at the 1-position of the benzimidazole ring led to an improvement in the affinity. The 5-HT3 receptor antagonist activity of compounds with higher affinity was performed by evaluating the inhibition of the 5-HT induced von Bezold-Jarisch reflex. They displayed moderate 5-HT3 antagonist activity (ED50 = 10.6–29.1 μg/kg i.v.)." @default.
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- W1990383544 date "1999-05-01" @default.
- W1990383544 modified "2023-10-16" @default.
- W1990383544 title "Benzimidazole-2-carboxylic acid amides and esters: a new structural class of 5-HT3 ligands" @default.
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- W1990383544 doi "https://doi.org/10.1016/s0223-5234(99)80091-9" @default.
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