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Synthesis of cis ‐4‐methyl‐3‐phenylpyrrolidines as potential dopaminergic agonists
Author(s) -
Crider A. Michael,
Sylvestri Susan C.,
Tschappat Kathryn D.,
Dick Ronald M.,
Leader W. Greg
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250527
Subject(s) - chemistry , dopaminergic , pyrrolidine , acylation , stereochemistry , medicinal chemistry , organic chemistry , dopamine , medicine , catalysis
cis ‐3‐(3,4‐Dihydroxyprienyl)4‐methyl‐1‐( n ‐propyl)pyrrolidine ( 23 ) was synthesized and evaluated for dopaminergic activity. The synthesis of 23 involved selective 4‐acylation of the 3‐phenylpyrrolidine‐2,5‐dione 15 and cis ‐addition of hydrogen to a 4‐methyl‐3‐phenyl‐3‐pyrroline 4 . Pharmacological evaluation of 23 showed that introduction of a cis ‐4‐methyl group into the 3‐phenylpyrrolidine nucleus decreases dopaminergic activity.