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Design, synthesis and pharmacological evaluation of novel naphthalenic derivatives as selective MT(1) melatoninergic ligands.

Abstract：

:Novel heterodimer analogues of melatonin were synthesized, when agomelatine (1) and various aryl units are linked via a linear alkyl chain through the methoxy group. The compounds were tested for their actions at melatonin receptors. Several of these ligands are MT(1)-selective with nanomolar or subnanomolar affinity. In addition, while most of the derivatives behave as partial agonists on one or both receptor subtypes, N-[2-(7-{4-[6-(1-methoxycarbonylethyl)naphthalen-2-yloxy]butoxy}naphthalen-1-yl)ethyl]acetamide (36), a subnanomolar MT(1) ligand with an 11-fold preference over MT(2) receptors, is a full antagonist on both receptors. Our results also confirm that the selectivity seen for the MT(1) receptor arises predominantly from steric factors and is not a consequence of the bridging of melatonin receptor dimers.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Mésangeau C,Pérès B,Descamps-François C,Chavatte P,Audinot V,Coumailleau S,Boutin JA,Delagrange P,Bennejean C,Renard P,Caignard DH,Berthelot P,Yous S

doi

10.1016/j.bmc.2010.04.008

subject

Has Abstract

pub_date

2010-05-15 00:00:00

pages

3426-36

issue

10

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(10)00310-X

journal_volume

18

pub_type

杂志文章

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