Matches in SemOpenAlex for { <https://semopenalex.org/work/W2950402901> ?p ?o ?g. }
Showing items 1 to 84 of
84
with 100 items per page.
- W2950402901 endingPage "527" @default.
- W2950402901 startingPage "523" @default.
- W2950402901 abstract "The enantiomers of the antimuscarinic agent 1-cyclohexyl-1-(4-fluorophenyl)-4-piperidino-1-butanol [(R)- and (S)-p-fluorohexahydro-difenidol] [(R)- and (S)-2a] and their methiodides (R)-3 and (S)-3 were prepared with high enantiomeric purity. (R)-2a and (S)-2a (isolated as hydrochlorides) were obtained by catalytic hydrogenation (Pd/C contact) of the corresponding enantiomers of 1-cyclohexyl-1-(4-fluorophenyl)-4-piperidino-2-butyn-1-ol [(R)- and (S)-4]. Reaction of (R)-2a and (S)-2a with methyl iodide led to (R)-3 and (S)-3, respectively. The unsaturated precursors (R)- and (S)-4 (enantiomeric purity ⩾99.80 and ⩾99.94% e.e.; calorimetric analysis) were prepared by resolution of rac-4 [available from 4-FC6H4C(O)C6H11 by reaction with LiCCCH2NC5H10] using (R)- and (S)-mandelic acid as resolving agents. The absolute configurations of the (R) and (S) enantiomers of 2a, 3, and 4 were determined by an X-ray crystal-structure analysis of (S)-5, the methiodide of (S)-4. (R)-2a and (R)-3 exhibit a higher affinity for muscarinic M1, M2, M3, and M4 receptors (by up to two orders of magnitude) than their corresponding antipodes (S)-2a and (S)-3, the degree of stereoselectivity depending on the receptor subtype involved. (R)-2a represents a useful tool for muscarinic receptor research (affinity profile: M1 ≈ M3 ≈ M4 > M2)." @default.
- W2950402901 created "2019-06-27" @default.
- W2950402901 creator A5019508817 @default.
- W2950402901 creator A5033600382 @default.
- W2950402901 creator A5039131612 @default.
- W2950402901 creator A5047144179 @default.
- W2950402901 creator A5051448005 @default.
- W2950402901 creator A5063401322 @default.
- W2950402901 creator A5089476171 @default.
- W2950402901 date "1991-06-13" @default.
- W2950402901 modified "2023-09-26" @default.
- W2950402901 title "Enantiomers of the muscarinic antagonist 1-cyclohexyl-1-(4-fluorophenyl)-4-piperidino-1-butanol (p-fluoro-hexahydro-difenidol): Synthesis, absolute configuration, and enantiomeric purity" @default.
- W2950402901 cites W1974864349 @default.
- W2950402901 cites W2007300751 @default.
- W2950402901 cites W2074756242 @default.
- W2950402901 cites W2078203628 @default.
- W2950402901 cites W2082118577 @default.
- W2950402901 cites W2131473945 @default.
- W2950402901 cites W2155933328 @default.
- W2950402901 cites W2755681404 @default.
- W2950402901 doi "https://doi.org/10.1002/jlac.199119910196" @default.
- W2950402901 hasPublicationYear "1991" @default.
- W2950402901 type Work @default.
- W2950402901 sameAs 2950402901 @default.
- W2950402901 citedByCount "5" @default.
- W2950402901 crossrefType "journal-article" @default.
- W2950402901 hasAuthorship W2950402901A5019508817 @default.
- W2950402901 hasAuthorship W2950402901A5033600382 @default.
- W2950402901 hasAuthorship W2950402901A5039131612 @default.
- W2950402901 hasAuthorship W2950402901A5047144179 @default.
- W2950402901 hasAuthorship W2950402901A5051448005 @default.
- W2950402901 hasAuthorship W2950402901A5063401322 @default.
- W2950402901 hasAuthorship W2950402901A5089476171 @default.
- W2950402901 hasBestOaLocation W29504029012 @default.
- W2950402901 hasConcept C146686406 @default.
- W2950402901 hasConcept C155647269 @default.
- W2950402901 hasConcept C161790260 @default.
- W2950402901 hasConcept C170493617 @default.
- W2950402901 hasConcept C178790620 @default.
- W2950402901 hasConcept C181647583 @default.
- W2950402901 hasConcept C185592680 @default.
- W2950402901 hasConcept C25170562 @default.
- W2950402901 hasConcept C2776888068 @default.
- W2950402901 hasConcept C3141732 @default.
- W2950402901 hasConcept C33789571 @default.
- W2950402901 hasConcept C486523 @default.
- W2950402901 hasConcept C55493867 @default.
- W2950402901 hasConcept C71240020 @default.
- W2950402901 hasConceptScore W2950402901C146686406 @default.
- W2950402901 hasConceptScore W2950402901C155647269 @default.
- W2950402901 hasConceptScore W2950402901C161790260 @default.
- W2950402901 hasConceptScore W2950402901C170493617 @default.
- W2950402901 hasConceptScore W2950402901C178790620 @default.
- W2950402901 hasConceptScore W2950402901C181647583 @default.
- W2950402901 hasConceptScore W2950402901C185592680 @default.
- W2950402901 hasConceptScore W2950402901C25170562 @default.
- W2950402901 hasConceptScore W2950402901C2776888068 @default.
- W2950402901 hasConceptScore W2950402901C3141732 @default.
- W2950402901 hasConceptScore W2950402901C33789571 @default.
- W2950402901 hasConceptScore W2950402901C486523 @default.
- W2950402901 hasConceptScore W2950402901C55493867 @default.
- W2950402901 hasConceptScore W2950402901C71240020 @default.
- W2950402901 hasIssue "6" @default.
- W2950402901 hasLocation W29504029011 @default.
- W2950402901 hasLocation W29504029012 @default.
- W2950402901 hasOpenAccess W2950402901 @default.
- W2950402901 hasPrimaryLocation W29504029011 @default.
- W2950402901 hasRelatedWork W1946388854 @default.
- W2950402901 hasRelatedWork W1956888186 @default.
- W2950402901 hasRelatedWork W1966994697 @default.
- W2950402901 hasRelatedWork W2006310246 @default.
- W2950402901 hasRelatedWork W2089322790 @default.
- W2950402901 hasRelatedWork W2118494099 @default.
- W2950402901 hasRelatedWork W291087767 @default.
- W2950402901 hasRelatedWork W2951541015 @default.
- W2950402901 hasRelatedWork W2980317626 @default.
- W2950402901 hasRelatedWork W4282831597 @default.
- W2950402901 hasVolume "1991" @default.
- W2950402901 isParatext "false" @default.
- W2950402901 isRetracted "false" @default.
- W2950402901 magId "2950402901" @default.
- W2950402901 workType "article" @default.