SYNTHESIS AND ANTIMUSCARINIC ACTIVITY OF 2-[N-(ETHYL)-(N-BETA-HYDROXYETHYL)]AMINOETHYL 2,2-DIPHENYLPROPIONATE, A METABOLITE OF APROPHEN

Authors
BROWN ND LEADER H PHILLIPS LR SMEJKAL RM GORDON RK CHIANG PK
Citation
Nd. Brown et al., SYNTHESIS AND ANTIMUSCARINIC ACTIVITY OF 2-[N-(ETHYL)-(N-BETA-HYDROXYETHYL)]AMINOETHYL 2,2-DIPHENYLPROPIONATE, A METABOLITE OF APROPHEN, Journal of pharmaceutical sciences, 82(6), 1993, pp. 563-564
Citations number
12
Categorie Soggetti
Chemistry,"Pharmacology & Pharmacy
Journal title
Journal of pharmaceutical sciences → ACNP
ISSN journal
00223549
Volume
82
Issue
6
Year of publication
1993
Pages
563 - 564
Database
ISI
SICI code
0022-3549(1993)82:6<563:SAAAO2>2.0.ZU;2-C
Abstract
The preparation of 2-[N-(ethyl)-(N-beta-hydroxyethyl)]amino-ethyl 2,2- diphenylpropionate (1), a metabolite of aprophen [2-diethylamineothyl 2,2-diphenylpropionate], is described. Hydrolysis of [2-(2-chloroethyl )ethylamino]ethyl acetate hydrochloride (2) in a basic solution, follo wed 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, b ut was approximately 10-fold less potent than the parent compound apro phen.