Synthesis and antimuscarinic activity of 2-[N-(ethyl)-(N-beta-hydroxyethyl)]aminoethyl 2,2-diphenylpropionate, a metabolite of aprophen
| Autor: | Lawrence R. Phillips, Ruthann M. Smejkal, Haim Leader, Peter K. Chiang, Richard K. Gordon, Nesbitt D. Brown |
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| Rok vydání: | 1993 |
| Předmět: |
Male
Magnetic Resonance Spectroscopy Hydrochloride Metabolite Guinea Pigs Ethyl acetate Pharmaceutical Science Medicinal chemistry Chemical synthesis Gas Chromatography-Mass Spectrometry Rats Sprague-Dawley Hydrolysis chemistry.chemical_compound Organic chemistry Animals Pancreas Cholinesterase chemistry.chemical_classification biology Phenylpropionates Muscle Smooth Amino acid Rats chemistry Parasympathomimetics Yield (chemistry) biology.protein alpha-Amylases Muscle Contraction |
| Zdroj: | Journal of pharmaceutical sciences. 82(6) |
| ISSN: | 0022-3549 |
| Popis: | The preparation of 2-[N-(ethyl)-(N-beta-hydroxyethyl)]amino-ethyl 2,2-diphenylpropionate (1), a metabolite of aprophen [2-diethylaminoethyl 2,2-diphenylpropionate], is described. Hydrolysis of [2-(2-chloroethyl)ethylamino]ethyl acetate hydrochloride (2) in a basic solution, followed by acidic pH adjustment, gave the ethylcholineaziridinium ion (3) that upon treatment with 2,2-diphenylpropionic acid produced 1 in a 56% yield. Synthetic 1 was found to possess antimuscarinic activities, but was approximately 10-fold less potent than the parent compound aprophen. |
| Databáze: | OpenAIRE |
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