Switch to
| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
6
|
| pubmed:dateCreated |
1980-9-26
|
| pubmed:abstractText |
N-Methylspiro[5-hydroxytetralin-1,3'-pyrrolidine] (2j) and N-methylspiro[7-hydroxytetralin-1,3'-pyrrolidine] (2n), conformationally restricted analogues of profadol, were synthesized via initial reaction of the appropriately substituted 1-tetralone with ethyl cyanoacetate to give the ethyl 1-tetralylidenecyanoacetate derivative (3), which was then reacted with KCN to give the corresponding 1-cyano-1-(cyanomethyl)tetralin (4). Treatment of 4 with either HBr in dry ether-dichloromethane or acetic acid-sulfuric acid afforded the spiro[tetralin-1,3'-pyrrolidine-2',5'-dione] derivative (5), which was then reduced with LiAlH4-THF and N-methylated with HCHO-HCO2H to give the appropriately substituted spiro[tetralin-1,3'-pyrrolidine] (2). Both 2j and 2n and the isomeric 6-hydroxy derivative 21 all showed no significant analgesic activity in hot-plate and writhing tests. However, spiro[tetralin-1,3'-pyrrolidine] (2a) and its N-methyl derivative (2b) both possessed codeine-level analgesic activity.
|
| pubmed:language |
eng
|
| pubmed:journal | |
| pubmed:citationSubset |
IM
|
| pubmed:chemical | |
| pubmed:status |
MEDLINE
|
| pubmed:month |
Jun
|
| pubmed:issn |
0022-2623
|
| pubmed:author | |
| pubmed:issnType |
Print
|
| pubmed:volume |
23
|
| pubmed:owner |
NLM
|
| pubmed:authorsComplete |
Y
|
| pubmed:pagination |
679-82
|
| pubmed:dateRevised |
2003-11-14
|
| pubmed:meshHeading | |
| pubmed:year |
1980
|
| pubmed:articleTitle |
Synthesis and analgesic properties of some conformationally restricted analogues of profadol.
|
| pubmed:publicationType |
Journal Article
|