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Solid-phase Organic Synthesis of Chiral, Non-Racemic 1,2,4-trisubstituted 1,4-diazepanes With High σ 1 Receptor Affinity

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Solid-phase Organic Synthesis of Chiral, Non-Racemic 1,2,4-trisubstituted 1,4-diazepanes With High σ 1 Receptor Affinity

Lena Fanter et al. Arch Pharm (Weinheim).

Abstract

The aim of this work was to transfer the established chiral-pool synthesis of 1,2,4-trisubstituted 1,4-diazepanes in solution on the solid phase. For this purpose, (S)-configured amino acids, (S)-alanine, and (S)-leucine, with a small methyl and a larger isobutyl moiety were attached to the solid support 9 by reductive amination. After five reaction steps on the solid support, the 1,4-diazepanes (S)-19a,b were cleaved off and reductively alkylated to afford the 1,2,4-trisubstituted 1,4-diazepanes (S)-20a and (S)-21b, respectively. Both compounds show high σ1 affinity and selectivity over the σ2 subtype.

Keywords: 1,2,4-trisubstituted 1,4-diazepanes; chiral-pool synthesis; solid-phase organic synthesis; subtype selectivity; σ1 receptor ligands.

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