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Design, synthesis and receptor affinity of novel conformationally restricted σ ligands based on the [4.3.3]propellane scaffold.

Abstract：

:A series of novel diastereoisomeric σ ligands 3 was designed, synthesized and pharmacologically evaluated. The highly rigid [4.3.3]propellane scaffold was used to fix the three dimensional orientation of the pharmacophoric moieties required for σ affinity. The syn,syn-configured aminocarbamate syn,syn-3a reveals the most promising σ₁ affinity (Ki = 77 nM) and selectivity over the σ₂ subtype (21-fold). The σ₂ affinity of all four diastereomers 3 was in the low micromolar range. Analysis of the distance between the hydrophobic regions (phenyl moieties) of the diastereomers 3 led to the longest range of distances (10.3-15.2 Å) for the most potent σ₁ ligand syn,syn-3a, which is in good agreement with pharmacophore models.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Torres-Gómez H,Lehmkuhl K,Schepmann D,Wünsch B

doi

10.1016/j.ejmech.2013.09.021

subject

Has Abstract

pub_date

2013-01-01 00:00:00

pages

78-87

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(13)00594-1

journal_volume

70

pub_type

杂志文章

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