Synthesis of cis-4-methyl-3-phenylpyrrolidines as potential dopaminergic agonists

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 eva...

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Bibliographic Details
Published in:	Journal of heterocyclic chemistry Vol. 25; no. 5; pp. 1407 - 1412
Main Authors:	Crider, A. Michael, Sylvestri, Susan C., Tschappat, Kathryn D., Dick, Ronald M., Leader, W. Greg
Format:	Journal Article
Language:	English
Published:	Hoboken Wiley-Blackwell 01-09-1988 Wiley‐Blackwell HeteroCorporation
Subjects:	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties Five membered ring Sympathomimetic Nitrogen heterocycle Diphenols Biological activity Cis stereoisomer
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Summary:	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.
Bibliography:	ArticleID:JHET5570250527 istex:5650E73FEEC69B2A72E3AE24A718C2581799A7E8 ark:/67375/WNG-DK8TC6TN-G School of Pharmacy at Northeast Louisiana University Northeast Louisiana University University of Toledo.
ISSN:	0022-152X 1943-5193
DOI:	10.1002/jhet.5570250527