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Egyptian Pharmaceutical Journal [National Research Center]. 2008; 7 (2): 189-200
in English | IMEMR | ID: emr-100908

ABSTRACT

The synthesis of a series of N-[[2R]-1-ethyl or propyl-2-[4-methoxybenzyl]-pyrrolidin-3-yl]-N-phenyl acetamide or propionamide [la-d] was achieved, where R, R=methyl or ethyl with the aim to evaluate their analgesic activity. The adopted synthetic pathway of these compounds was illustrated Dieckmann cyclization of 2-[acyl-[2-ethoxycarboryl-ethyl]-amino]-3-[4-methoxy-phenyl]-propionic acid ethyl ester [7a, b] afforded [R]-ethyl 1-acetyl or propionyl-5-[4-methoxybenzyl]-4-oxopyrrolidine-3-carboxylate [6a and 6b], followed by deethoxycarboxylation. The target compounds 1a-d were synthesized Screening of the analgesic profile of the synthesized compounds showed that compounds 1b and 1c at dose level of 0.13mmol/kg. I p. exhibited the highest analgesic activity compared with morphine hydrochloride [0.004 mmol/kg. i.p]


Subject(s)
Analgesics/chemical synthesis , Amides/chemical synthesis , Acetanilides/chemical synthesis
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