Synthesis and antimuscarinic activity of 2-[N-(ethyl)-(N-beta-hydroxyethyl)]aminoethyl 2,2-diphenylpropionate, a metabolite of aprophen.
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.
Brown
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ND
Applied Biochemistry Branch, Walter Reed Army Institute of Research, Washington, DC 20307-5100.
Leader
H
H
Phillips
L R
LR
Smejkal
R M
RM
Gordon
R K
RK
Chiang
P K
PK
D000818:Animals; D008401:Gas Chromatography-Mass Spectrometry; D006168:Guinea Pigs; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D009119:Muscle Contraction / Q000187:drug effects; D009130:Muscle, Smooth / Q000187:drug effects / Q000378:metabolism; D010179:Pancreas / Q000187:drug effects / Q000201:enzymology; D010277:Parasympathomimetics / Q000009:adverse effects* / Q000494:pharmacology; D010666:Phenylpropionates / Q000138:chemical synthesis* / Q000494:pharmacology*; D051381:Rats; D017207:Rats, Sprague-Dawley; D000516:alpha-Amylases / Q000037:antagonists & inhibitors / Q000378:metabolism
D010277:Parasympathomimetics; D010666:Phenylpropionates; C069444:beta-hydroxyethylaprophen; D000516:alpha-Amylases