UCL logo

UCL Discovery

UCL home » Library Services » Electronic resources » UCL Discovery

Substituted benzamides with conformationally restricted side chains. 1. Quinolizidine derivatives as selective gastric prokinetic agents.

Hadley, MS; King, FD; McRitchie, B; Turner, DH; Watts, EA; (1985) Substituted benzamides with conformationally restricted side chains. 1. Quinolizidine derivatives as selective gastric prokinetic agents. J Med Chem , 28 (12) pp. 1843-1847.

Full text not available from this repository.

Abstract

The gastric prokinetic action of metoclopramide may not be primarily due to its dopamine antagonist activity. The present aim was to obtain a selective gastric prokinetic agent lacking dopamine antagonist activity by conformationally restricting the side chain of metoclopramide. In a series of quinolizidinylbenzamides, only compounds with the benzamide moiety at position 2 of the quinolizidine ring retain gastric activity. Of these 2-substituted compounds, the 2 alpha, 9a alpha isomer has potent selective gastric prokinetic activity with only weak dopamine antagonist properties. Spectroscopic data show that the quinolizidine ring preferentially adopts a trans chair-chair conformation with an axial benzamide moiety. However, energy calculations indicate that, at nondopaminergic receptors controlling gastric motility, an alternative cis chair-chair conformation with an equatorial benzamide moiety cannot be ruled out.

Type: Article
Title: Substituted benzamides with conformationally restricted side chains. 1. Quinolizidine derivatives as selective gastric prokinetic agents.
Location: United States
Keywords: Animals, Benzamides, Chemical Phenomena, Chemistry, Dopamine, Dopamine Antagonists, Gastrointestinal Motility, Male, Metoclopramide, Molecular Conformation, Pressure, Quinolizines, Rats, Rats, Inbred Strains, Receptors, Dopamine, Structure-Activity Relationship
UCL classification: UCL > School of BEAMS
UCL > School of BEAMS > Faculty of Maths and Physical Sciences
URI: http://discovery.ucl.ac.uk/id/eprint/1373405
Downloads since deposit
0Downloads
Download activity - last month
Download activity - last 12 months
Downloads by country - last 12 months

Archive Staff Only

View Item View Item