1360685-07-9Relevant academic research and scientific papers
Oxa-Pictet–Spengler reaction as key step in the synthesis of novel σ receptor ligands with 2-benzopyran structure
Knappmann, Inga,Schepmann, Dirk,Wünsch, Bernhard
, p. 4045 - 4055 (2016)
The Oxa-Pictet–Spengler reaction of methyl 3-hydroxy-4-phenylbutanoate (8) was explored to obtain novel σ receptor ligands. 1-Acyl protected piperidone ketals 10 and 11 reacted with phenylethanol 8 to yield spirocyclic compounds. Aliphatic aldehyde acetals 19 provided 1,3-disubstituted 2-benzopyrans 20 with high cis-diastereoselectivity. The intramolecular Oxa-Pictet–Spengler reaction of 24 led to the tricyclic compound 25. The spirocyclic compounds 18 show high σ1affinity (Ki20–26?nM) and σ1/σ2selectivity (>9-fold), when a large substituent (n-octyl, benzyl, phenylpropyl) is attached to the piperidine N-atom. Opening of the piperidine ring to yield aminoethyl (22, 23) or aminomethyl derivatives (21) resulted in reduced σ1affinity and σ1/σ2selectivity.
Pyrido-pyrimidine derivatives, preparation thereof, and therapeutic use thereof
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Page/Page column 9, (2008/06/13)
The disclosure concerns pyrido[2,3-d]pyrimidine derivatives, their preparation and their therapeutic application, of general formula (I) and acid addition salts, hydrates and solvates thereof, as well as in the form of enantiomers, diastereoisomers and mixtures thereof. The disclosure also concerns methods for preparing said derivatives, pharmaceutical compositions containing a compound of general formula (I), and their therapeutic use.
