Synthesis of σ Receptor Ligands with a Spirocyclic System Connected with a Tetrahydroisoquinoline Moiety via Different Linkers.

ABSTRACT: With the aim to develop new σ₂ receptor ligands, spirocyclic piperidines or cyclohexanamines with 2-benzopyran and 2-benzofuran scaffolds were connected to the 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline moiety by variable linkers. In addition to flexible alkyl chains, linkers containing an amide as functional group were synthesized. The 2-benzopyran and 2-benzofuran scaffold of the spirocyclic compounds were synthesized from 2-bromobenzaldehyde. The amide linkers were constructed by acylation of amines with chloroacetyl chloride and subsequent nucleophilic substitution, the alkyl linkers were obtained by LiAlH₄ reduction of the corresponding amides. For the development of σ₂ receptor ligands, the spirocyclic 2-benzopyran scaffold is more favorable than th

SUBMITTER: Bergkemper M 

PROVIDER: S-EPMC8048568 | biostudies-literature | 2021 Apr

REPOSITORIES: biostudies-literature