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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
12
|
| pubmed:dateCreated |
1995-7-14
|
| pubmed:abstractText |
New melatonin-like agents were designed from the frameworks of 2,5-dimethoxyphenethylamine, an important structural moiety for the 5-HT receptor, and (2-methoxynaphthyl)-ethylamine. The compounds were synthesized by classical methods and evaluated in binding assays with chicken brain membranes using 2-[125I]iodomelatonin as the radioligand. Preliminary studies on the series of N-acyl-disubstituted phenethylamines showed the favorable role of the methoxy group in the ortho position of the side chain on the affinity for the receptor (Ki = 8 +/- 0.2 nM) for N-[2-(2-methoxy-5-bromophenyl)ethyl]propionamide (3o). This effect was confirmed in a series of the naphthalene derivatives, a bioisosteric moiety of the indole ring, and several potent ligands for melatonin binding sites were prepared such as N-[2-(2-methoxynaphthyl)ethyl]propionamide (4b) (Ki = 0.67 +/- 0.05 nM) and N-[2-(2,7-dimethoxynaphthyl)ethyl]cyclopropylformamide (Ki = 0.05 +/- 0.004 nM) (4k). Structure-activity relationships are discussed with regard to melatonin and bioisosteric naphthalenic compound 2. The Ki value for 4b was affected to a similar extent to that of melatonin by GTP-gamma-S or Mn2+ in competition experiments, suggesting an agonist profile for this compound.
|
| pubmed:language |
eng
|
| pubmed:journal | |
| pubmed:citationSubset |
IM
|
| pubmed:chemical | |
| pubmed:status |
MEDLINE
|
| pubmed:month |
Jun
|
| pubmed:issn |
0022-2623
|
| pubmed:author | |
| pubmed:issnType |
Print
|
| pubmed:day |
9
|
| pubmed:volume |
38
|
| pubmed:owner |
NLM
|
| pubmed:authorsComplete |
Y
|
| pubmed:pagination |
2050-60
|
| pubmed:dateRevised |
2003-11-14
|
| pubmed:meshHeading |
pubmed-meshheading:7783136-Animals,
pubmed-meshheading:7783136-Binding Sites,
pubmed-meshheading:7783136-Chickens,
pubmed-meshheading:7783136-Drug Design,
pubmed-meshheading:7783136-Iodine Radioisotopes,
pubmed-meshheading:7783136-Ligands,
pubmed-meshheading:7783136-Magnetic Resonance Spectroscopy,
pubmed-meshheading:7783136-Melatonin,
pubmed-meshheading:7783136-Naphthalenes,
pubmed-meshheading:7783136-Radioligand Assay,
pubmed-meshheading:7783136-Structure-Activity Relationship
|
| pubmed:year |
1995
|
| pubmed:articleTitle |
Design and synthesis of new naphthalenic derivatives as ligands for 2-[125I]iodomelatonin binding sites.
|
| pubmed:affiliation |
CNRS-BIOCIS, Faculté de Pharmacie, Châtenay-Malabry, France.
|
| pubmed:publicationType |
Journal Article
|