Esters of Bicyclic Aminoalcohols as Potential Anticholinergics III

Martell, Michael J.; Soine, Taito O.

doi:10.1002/jps.2600520404

Cited by 10 publications

(2 citation statements)

References 19 publications

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“…After stirring the reaction mixture at 0 °C for 1 h, a solution of the oxime derivative (2.1 g, 0.013 mol) in dry THF (100 mL) was added over 30 min and the whole was heated under reflux for 2.5 h before cooling to 0 °C. Sequential treatment with H20 (1.5 mL), 10 N NaOH (2.2 mL), and H20 (3.8 mL), filtration, and concentration of the filtrate gave the title compound (1.78 g 98%), used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Substituted benzamides with conformationally restricted side chains. 5. Azabicyclo[x.y.z] derivatives as 5-HT4 receptor agonists and gastric motility stimulants

King

Hadley²,

Joiner³

et al. 1993

J. Med. Chem.

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The syntheses of benzamides containing azabicyclo[x.y.z] side chains and their 5-HT4 receptor agonist and 5-HT3 receptor antagonist properties are described. These compounds were designed to mimic higher energy conformations of quinolizidine and indolizidine. High potency was achieved for both activities although an exactly paralleling SAR was not apparent. Introduction of O and S resulted in only marginal differences in potency which was more apparent for 5-HT3 antagonism. The introduction of a methyl group alpha to the basic nitrogen resulted in a reduction in 5-HT4 receptor agonist potency. Renzapride (5f) was identified for further evaluation for which both enantiomers had an identical pharmacological profile, as did an azatricyclic 9b, which contained a combination of the steric bulk of the two separate enantiomers.

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Section: Methodsmentioning

confidence: 99%

Substituted benzamides with conformationally restricted side chains. 5. Azabicyclo[x.y.z] derivatives as 5-HT4 receptor agonists and gastric motility stimulants

King

Hadley²,

Joiner³

et al. 1993

J. Med. Chem.

View full text Add to dashboard Cite

show abstract

“…This technique was found to be reliable and convenient. Most of these studies utilized the method for the analysis of aqueous solutions of organic compounds (1)(2)(3)(4)(5)(6)(7)(8). In only a few instances has this method been applied to the determination of water in natural products.…”

Section: By Nouri Y Marymentioning

confidence: 99%