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Is a Nitrogen Atom an Important Pharmacophoric Element in Sigma Ligand Binding?

2000; Elsevier BV; Volume: 8; Issue: 8 Linguagem: Inglês

10.1016/s0968-0896(00)00148-6

1464-3391

Seth Y. Ablordeppey, James B. Fischer, Richard A. Glennon,

N-Heterocyclic Carbenes in Organic and Inorganic Chemistry

A lingering question in σ receptor ligand development is whether a nitrogen atom serves as an important pharmacophoric element in binding affinity. To address this question, we have synthesized several phenylalkylpiperidines and phenylalkylpiperazines and demonstrated that removal of the N atom from a typical phenylalkylpiperidine led to little or no binding to σ receptors. In addition, where two N atoms occur in a compound, such as with phenylalkylpiperazines, the N atom on the longer alkyl chain appears to be more important. Thus, based on this study, the N atom is an important pharmacophoric element in the binding of phenylalkylpiperidines and phenylalkylpiperazines to σ receptors.