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rdf:type |
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lifeskim:mentions |
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pubmed:issue |
9
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pubmed:dateCreated |
2002-4-18
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pubmed:abstractText |
The aim of this study was to synthesize selective ligands for melatoninergic subtype receptors that could elucidate the physiological role of melatonin (N-acetyl-5-methoxytryptamine, 1). So, we first investigated the role of a nitro substituent in the 4-, 6-, or 7-position of the indole heterocycle. Comparatively to melatonin, its analogues that nitrated in the 6- or 7-position (6 and 22) lose MT(3) but retain good MT(1) and MT(2) affinities, whereas the 4-nitro isomer (5) shows very high affinity (nanomolar) and selectivity for the MT(3) binding sites. N-Methylation of the indole nucleus of compound 5 potentiates these effects and affords the most potent and selective MT(3) ligand (17). The 2-iodo derivatives (12 and 10) of compounds 5 and 17 have also been synthesized to evaluate their binding profile with a view to further develop MT(3) selective radioligands.
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pubmed:language |
eng
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pubmed:journal |
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pubmed:citationSubset |
IM
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pubmed:chemical |
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pubmed:status |
MEDLINE
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pubmed:month |
Apr
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pubmed:issn |
0022-2623
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pubmed:author |
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pubmed:issnType |
Print
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pubmed:day |
25
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pubmed:volume |
45
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
1853-9
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading |
pubmed-meshheading:11960497-Acetamides,
pubmed-meshheading:11960497-Animals,
pubmed-meshheading:11960497-Binding Sites,
pubmed-meshheading:11960497-Cell Line,
pubmed-meshheading:11960497-Cricetinae,
pubmed-meshheading:11960497-Humans,
pubmed-meshheading:11960497-Indoles,
pubmed-meshheading:11960497-Ligands,
pubmed-meshheading:11960497-Nitro Compounds,
pubmed-meshheading:11960497-Radioligand Assay,
pubmed-meshheading:11960497-Receptors, Cell Surface,
pubmed-meshheading:11960497-Receptors, Cytoplasmic and Nuclear,
pubmed-meshheading:11960497-Receptors, Melatonin,
pubmed-meshheading:11960497-Structure-Activity Relationship
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pubmed:year |
2002
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pubmed:articleTitle |
Synthesis of nitroindole derivatives with high affinity and selectivity for melatoninergic binding sites MT(3).
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pubmed:affiliation |
Institut de Chimie Pharmaceutique Albert Lespagnol, 3 rue du Professeur Laguesse, BP83, 59006 Lille Cedex, France.
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pubmed:publicationType |
Journal Article,
In Vitro
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