Synthesis and receptor activity of 2-substituted 8-methyl-5-(2-pyridinylethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles

A series of new 2-substituted 8-methyl-5-(2-pyridinylethyl)-2,3,4,5-tetrahydro-1 H -pyrido[4,3- b ]indoles have been synthesized. Their activity profiles were studied on a broad panel of therapeutic targets including GPC-receptors, ion channels, and neurotransmitter transporters. One of the studied...

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Veröffentlicht in:Pharmaceutical chemistry journal 2013-04, Vol.47 (1), p.12-19
Hauptverfasser: Ivachtchenko, A. V., Mitkin, O. D., Kysil, V. M., Kazey, V. I., Okun, I. M.
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Sprache:eng
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Zusammenfassung:A series of new 2-substituted 8-methyl-5-(2-pyridinylethyl)-2,3,4,5-tetrahydro-1 H -pyrido[4,3- b ]indoles have been synthesized. Their activity profiles were studied on a broad panel of therapeutic targets including GPC-receptors, ion channels, and neurotransmitter transporters. One of the studied compounds, 2-methyl-3-{2-[8-methyl-5-(2-pyridin-2-ylethyl)-2,3,4,5-tetrahydropyridino[4,3- b ]indol-2-yl]ethyl}-6,7,8,9-tetrahydropyrido[1,2- a ]pyrimidin-4-one, was found to be a highly active antagonist of adrenergic α 1A , α 1B , α 1D , and α 2A receptors and serotonin 5-HT 2A , 5-HT 2B , 5-HT 2C , and 5-HT 7 receptors. The results were considered in terms of structure—activity relationships. It was established that introduction of bulky substituents into the 2-position of the other synthesized 8-methyl-5-(2-pyridinylethyl)-2,3,4,5-tetrahydro-1 H -pyrido[4,3- b ]indoles led to an activity decrease of the corresponding derivatives as compared with that of the 2,8-dimethyl analogs.
ISSN:0091-150X
1573-9031
DOI:10.1007/s11094-013-0887-4