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Synthesis and evaluation of N 1-alkylindole-3-ylalkylammonium compounds as nicotinic acetylcholine receptor ligands
Keywords: rat, synthesis, binding, structure, receptor, paper, methyl, tissue, indole, affinity, drug, iodide, activity, amine, tryptamine, controlled, animal, relation, study, 1, 3, bryozoa, derivative, nonhuman, 2, 1h, (1, indol, conference, (3, unclassified, nicotinic, n, dimethyl, unindexed, [2, b, 1,2, dione, yl), n,n, [1, bungarotoxin, trimethyl, n1, carbaldehyde, Gymnolaemata, alpha4beta2, yl)ethyl], octyl, carboxamide, enyl), dimethyltryptamine, (1H, (pyrrolidin, methylbut, yl)ethane, yl]ethyl]pyrrolidinium, oxoacetamide, dimethylpropanamide, deformylflustrabromine, yl)ethanamine, n10,n10, yl)propan, yl)propanamide, dimethyl(1, yl)methanamine, octylgramine, dimethyl[1, yl]methanamine, prenylgramine, trimethyl[1, yl]methanaminium, prenylgraminium, n,n,n, yl)ethanaminium, n10,n10,n10, trimethyltryptaminium, aminium, trimethyl(1, yl)methanaminium, octylgraminium, alkylindole, ylalkylammonium, n1,n10, n10, boc, n1,n10,n10, trimethyltryptamine, n1,n10,n10,n10, tetramethyltryptaminium, (alpha1), 2beta1gammadelta, alpha3beta4, Flustra, foliacea
Abstract
In this study thirty-three novel indole derivatives were designed and synthesized based on the structure of deformylflustrabromine B (1), a metabolite isolated from the marine bryozoan Flustra foliacea L. The syntheses were carried out using standard methodologies and in good yields. The molecules were tested for their affinities for the ?4?2*, ?3? 4*, ?7* and (?1) 2?1?? nicotinic acetylcholine receptor (nAChR) subtypes. Binding assays showed that, among these ligands, compound 7c exhibited the highest affinity with K i = 136.1, 93.9 and 862.4 nM for the ?4?2*, ?3?4*, and ?7* nAChRs subtypes, respectively. These results indicated that the indole core might be a useful scaffold for the development of new potent and selective nAChR ligands. © 2012 Elsevier Ltd. All rights reserved.
Más información
| Título de la Revista: | BIOORGANIC AND MEDICINAL CHEMISTRY |
| Volumen: | 20 |
| Número: | 12 |
| Editorial: | Elsevier |
| Fecha de publicación: | 2012 |
| Página de inicio: | 3719 |
| Página final: | 3727 |
| URL: | http://www.scopus.com/inward/record.url?eid=2-s2.0-84861578490&partnerID=q2rCbXpz |