Design and synthesis of 1-(2-alkanamidoethyl)-6-methoxy-7-azaindole derivatives as potent melatonin agonists.
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Jeanty M, Suzenet F, Delagrange P, Nosjean O, Boutin JA, Caignard DH, Guillaumet G
Design and synthesis of 1-(2-alkanamidoethyl)-6-methoxy-7-azaindole derivatives as potent melatonin agonists.
Bioorg Med Chem Lett. 2011 Apr 15;21(8):2316-9. doi: 10.1016/j.bmcl.2011.02.097. Epub 2011 Feb 26.
- PubMed ID
- 21420861 [ View in PubMed]
- Abstract
A series of 7-azaindolic ligands bearing a methoxy group and a N-acetyl chain as melatoninergic pharmacophores were synthesized and their binding affinities towards MT(1) and MT(2) receptors were evaluated. Compounds 7a-c and 12 (cyclohexyl ring connected at C-2 and C-3 position) appears as important melatonin MT(2) and MT(1) receptors agonists. On the other hand, the presence of basic groups (amines) at position C-3 was detrimental to the melatoninergic affinities.
DrugBank Data that Cites this Article
- Binding Properties
Drug Target Property Measurement pH Temperature (°C) Melatonin Melatonin receptor type 1A Ki (nM) 0.25 N/A N/A Details Melatonin Melatonin receptor type 1A EC 50 (nM) 1.5 N/A N/A Details Melatonin Melatonin receptor type 1B Ki (nM) 0.34 N/A N/A Details Melatonin Melatonin receptor type 1B EC 50 (nM) 0.42 N/A N/A Details