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 |
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| creator | Ivachtchenko, A. V. Mitkin, O. D. Kysil, V. M. Kazey, V. I. Okun, I. M. |
| description | 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. |
| doi_str_mv | 10.1007/s11094-013-0887-4 |
| format | Article |
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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.</description><identifier>ISSN: 0091-150X</identifier><identifier>EISSN: 1573-9031</identifier><identifier>DOI: 10.1007/s11094-013-0887-4</identifier><language>eng</language><publisher>Boston: Springer US</publisher><subject>Medicine ; Organic Chemistry ; Pharmacology/Toxicology ; Pharmacy</subject><ispartof>Pharmaceutical chemistry journal, 2013-04, Vol.47 (1), p.12-19</ispartof><rights>Springer Science+Business Media New York 2013</rights><rights>COPYRIGHT 2013 Springer</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c279t-93ae976b777633201d3f30fedd4aa5831c8f41a29213b44f060fd846886675b93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11094-013-0887-4$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11094-013-0887-4$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>315,781,785,27929,27930,41493,42562,51324</link.rule.ids></links><search><creatorcontrib>Ivachtchenko, A. V.</creatorcontrib><creatorcontrib>Mitkin, O. D.</creatorcontrib><creatorcontrib>Kysil, V. M.</creatorcontrib><creatorcontrib>Kazey, V. I.</creatorcontrib><creatorcontrib>Okun, I. M.</creatorcontrib><title>Synthesis and receptor activity of 2-substituted 8-methyl-5-(2-pyridinylethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles</title><title>Pharmaceutical chemistry journal</title><addtitle>Pharm Chem J</addtitle><description>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.</description><subject>Medicine</subject><subject>Organic Chemistry</subject><subject>Pharmacology/Toxicology</subject><subject>Pharmacy</subject><issn>0091-150X</issn><issn>1573-9031</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp9kE1r3DAQhkVJoZs0P6A3HxvYSUcftuRjCPmCQA9toVCCkC0pq-C1Fklb8L-PUvcc5jAwvM8w8xDyheIlRZTfMqXYC0DKAZWSID6QDW0lhx45PSEbxJ4CbfH3J3Ka8wtipTjbkOXHMpedyyE3ZrZNcqM7lJgaM5bwN5Slib5hkI9DLqEci7ONgr0ru2WCFr4yOCwp2DAv07_ZBbAt34ptC8WVZHaLTRHo_ZqKf8SWw_AUZhsnlz-Tj95M2Z3_72fk1-3Nz-t7ePx-93B99Qgjk32BnhvXy26QUnacM6SWe47eWSuMaRWno_KCGtYzygchPHborRKdUl0n26HnZ-Ry3ftsJqfD7GO9bKxl3T6McXY-1PkV550SgrG2AnQFxhRzTs7rQwp7kxZNUb_J1qtsXWXrN9laVIatTK7Z-dkl_RKPaa5_vQO9Apt1gLs</recordid><startdate>20130401</startdate><enddate>20130401</enddate><creator>Ivachtchenko, A. V.</creator><creator>Mitkin, O. D.</creator><creator>Kysil, V. M.</creator><creator>Kazey, V. I.</creator><creator>Okun, I. M.</creator><general>Springer US</general><general>Springer</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20130401</creationdate><title>Synthesis and receptor activity of 2-substituted 8-methyl-5-(2-pyridinylethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles</title><author>Ivachtchenko, A. V. ; Mitkin, O. D. ; Kysil, V. M. ; Kazey, V. I. ; Okun, I. M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c279t-93ae976b777633201d3f30fedd4aa5831c8f41a29213b44f060fd846886675b93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Medicine</topic><topic>Organic Chemistry</topic><topic>Pharmacology/Toxicology</topic><topic>Pharmacy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ivachtchenko, A. V.</creatorcontrib><creatorcontrib>Mitkin, O. D.</creatorcontrib><creatorcontrib>Kysil, V. M.</creatorcontrib><creatorcontrib>Kazey, V. I.</creatorcontrib><creatorcontrib>Okun, I. M.</creatorcontrib><collection>CrossRef</collection><jtitle>Pharmaceutical chemistry journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ivachtchenko, A. V.</au><au>Mitkin, O. D.</au><au>Kysil, V. M.</au><au>Kazey, V. I.</au><au>Okun, I. M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and receptor activity of 2-substituted 8-methyl-5-(2-pyridinylethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles</atitle><jtitle>Pharmaceutical chemistry journal</jtitle><stitle>Pharm Chem J</stitle><date>2013-04-01</date><risdate>2013</risdate><volume>47</volume><issue>1</issue><spage>12</spage><epage>19</epage><pages>12-19</pages><issn>0091-150X</issn><eissn>1573-9031</eissn><abstract>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.</abstract><cop>Boston</cop><pub>Springer US</pub><doi>10.1007/s11094-013-0887-4</doi><tpages>8</tpages></addata></record> |
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| language | eng |
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| source | SpringerNature Journals |
| subjects | Medicine Organic Chemistry Pharmacology/Toxicology Pharmacy |
| title | Synthesis and receptor activity of 2-substituted 8-methyl-5-(2-pyridinylethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles |
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