Bivalent ligand approach on N-{2-((3-methoxyphenyl)methylamino)ethyl}acetamide: synthesis, binding affinity and intrinsic activity for MT(1) and MT(2) melatonin receptors.

Spadoni G; Bedini A; Orlando PLucarini STarzia GMor MRivara SLucini VPannacci MScaglione F

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Bivalent ligand approach on N-{2-((3-methoxyphenyl)methylamino)ethyl}acetamide: synthesis, binding affinity and intrinsic activity for MT(1) and MT(2) melatonin receptors.

机译：Bivalent ligand approach on N-{2-((3-methoxyphenyl)methylamino)ethyl}acetamide: synthesis, binding affinity and intrinsic activity for MT(1) and MT(2) melatonin receptors.

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摘要

We report the synthesis, binding properties and intrinsic activity at MT(1) and MT(2) melatonin receptors of new dimeric melatonin receptor ligands in which two units of the monomeric agonist N-{2-[(3-methoxyphenyl)methylamino]ethyl}acetamide (1) are linked together through different anchor points. Dimerization of compound 1 through the methoxy substituent leads to a substantial improvement in selectivity for the MT(1) receptor, and to a partial agonist behavior. Compound 3a, with a trimethylene linker, was the most selective for the MT(1) subtype (112-fold selectivity) and compound 3d, characterized by a hexamethylene spacer, had the highest MT(1) binding affinity (pK(iMT1)=8.47) and 54-fold MT(1)-selectivity. Dimerization through the aniline nitrogen of 1 abolished MT(1) selectivity, leading to compounds with either a full agonist or an antagonist behavior depending on the nature of the linker.

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《Bioorganic and medicinal chemistry》 |2011年第16期|4910-4916|共7页
作者
Spadoni G; Bedini A; Orlando PLucarini STarzia GMor MRivara SLucini VPannacci MScaglione F;
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Dipartimento di Scienze Biomolecolari, Universita degli Studi di Urbino Carlo Bo, Piazza Rinascimento 6, 61029 Urbino, Italy.;

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中图分类药学;
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Bivalent ligand approach on N-{2-((3-methoxyphenyl)methylamino)ethyl}acetamide: synthesis, binding affinity and intrinsic activity for MT(1) and MT(2) melatonin receptors.

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