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Synthesen und pharmakologische Eigenschaften von 2,2-Dialkyl-5-aryl-3-pyridylpyrrolidinen

✍ Scribed by Lislott Aeppli; Karl Bernauer; Fernand Schneider; Konrad Strub; Willi E. Oberhänsli; Karl-Heinz Pfoertner

Publisher
John Wiley and Sons
Year
1980
Tongue
German
Weight
922 KB
Volume
63
Category
Article
ISSN
0018-019X

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✦ Synopsis

Syntheses and Pharmacological Properties of 2,2‐Dialkyl‐5‐aryl‐3‐pyridylpyrrolidines

Reaction of the photochemically generated benzonitrile methylides 2 with vinylpyridines yields 2‐aryl‐4‐pyridyl‐1‐pyrrolines 3. Depending on reduction methods, the compounds 3 are selectively transformed to the corresponding cis‐ or the trans‐substituted pyrrolidines 10 or 11, respectively. Furthermore, a non‐photochemical synthesis has been developed: the easily available nitro‐ketones 8 provide through reductive cyclization the pyrrolines 3 or directly the pyrrolidines 11. Twenty‐seven compounds of types 10 and 11 have been evaluated in the writhing, hot plate and kaolin tests; especially the cis‐pyrrolidines 10 exhibit a valuable antinociceptive activity. Some of the pyrrolines and pyrrolidines have been separated into their enantiomers, which are easily interconverted.

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