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Synthesis of beta-substituted naphth-1-yl ethylamido derivatives as new melatoninergic agonists.

Abstract：

:Naphthalene melatoninergic ligands with alkyl groups (Me, Et, Pr, Bz) in the beta position of the ethylamido chain were synthesised. The affinity of the compounds for chicken brain melatonin receptors was evaluated using 2-[125I]-iodomelatonin as the radioligand. An increase in the affinity was observed with the beta-methyl derivatives and the greatest increase was seen with the (-) enantiomers. The introduction of a 2- or 7-MeO group on the naphthalene ring and the lengthening (Et, Pr) of the alkylamido chain gave potent compounds such as (-)1h (Ki = 24 pM). The functional activity of these compounds was evaluated by the aggregation of melanophores in Xenopus laevis tadpoles. The potency to produce lightening of the skin of Xenopus laevis was related to the affinities values of the molecules at melatonin chicken brain receptors. The most potent ligands were found to be full agonists and compound 1h was 25 fold more potent than melatonin in this bioassay.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Mathé-Allainmat M,Le Gall M,Jellimann C,Andrieux J,Langlois M

doi

10.1016/s0968-0896(99)00236-9

subject

Has Abstract

pub_date

1999-12-01 00:00:00

pages

2945-52

issue

12

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(99)00236-9

journal_volume

7

pub_type

杂志文章

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