5-(Sulfonyl)oxy-tryptamines and ethylamino side chain restricted derivatives. Structure-affinity relationships for h5-HT1B and h5-HT1D receptors
A number of sulfonic acid ester derivatives of serotonin (5-hydroxytryptamine; 5-HT; 1) were prepared and their affinities are compared to that of the reference compound 5-[[(trifluoromethyl)sulfonyl]oxy]-tryptamine (8b). The structure-affinity relationship (SAFIR) is discussed in terms of in vitro...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 1998-09, Vol.6 (9), p.1469-1479 |
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| creator | Barf, T Wikström, H Pauwels, P J Palmier, C Tardif, S Lundmark, M Sundell, S |
| description | A number of sulfonic acid ester derivatives of serotonin (5-hydroxytryptamine; 5-HT; 1) were prepared and their affinities are compared to that of the reference compound 5-[[(trifluoromethyl)sulfonyl]oxy]-tryptamine (8b). The structure-affinity relationship (SAFIR) is discussed in terms of in vitro binding for cloned human h5-HT1A, h5-HT1B and h5-HT1D receptors. All tryptamine derivatives exhibited the best affinities for h5-HT1D receptors but still, these were comparatively lower than that of compound 8b. 5-Tosylated tryptamine 11b (Ki = 6 nM) and the sulfamate derivatives 13b and 14b (Ki = 7 and 11 nM, respectively) were found to have the highest affinities for the h5-HT1D receptor. Other tryptamine derivatives displayed moderate binding for h5-HT1A and h5-HT1B receptors, along with Ki values ranging from 14-20 nM for the h5-HT1D sites. In addition, the syntheses of two alkylamino side chain restricted derivatives are described. 3-Amino-6-[[(trifluoromethyl)sulfonyl]oxy]-1,2,3,4-tetrahydrocarbazol e 21, as well as 4-[5-[[(trifluoromethyl)sulfonyl]oxy]-1H-indol-3-yl]piperidines 24 and 25, induced a shift in selectivity in favor of the h5-HT1B receptor. The relatively longer distance between the basic amine and a hydrogen-bond accepting oxygen in 21, 24 and 25 as compared to the non-restricted tryptamines, is likely responsible for this observation. |
| doi_str_mv | 10.1016/S0968-0896(98)00079-0 |
| format | Article |
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Structure-affinity relationships for h5-HT1B and h5-HT1D receptors</title><source>MEDLINE</source><source>ScienceDirect Journals (5 years ago - present)</source><creator>Barf, T ; Wikström, H ; Pauwels, P J ; Palmier, C ; Tardif, S ; Lundmark, M ; Sundell, S</creator><creatorcontrib>Barf, T ; Wikström, H ; Pauwels, P J ; Palmier, C ; Tardif, S ; Lundmark, M ; Sundell, S</creatorcontrib><description>A number of sulfonic acid ester derivatives of serotonin (5-hydroxytryptamine; 5-HT; 1) were prepared and their affinities are compared to that of the reference compound 5-[[(trifluoromethyl)sulfonyl]oxy]-tryptamine (8b). The structure-affinity relationship (SAFIR) is discussed in terms of in vitro binding for cloned human h5-HT1A, h5-HT1B and h5-HT1D receptors. All tryptamine derivatives exhibited the best affinities for h5-HT1D receptors but still, these were comparatively lower than that of compound 8b. 5-Tosylated tryptamine 11b (Ki = 6 nM) and the sulfamate derivatives 13b and 14b (Ki = 7 and 11 nM, respectively) were found to have the highest affinities for the h5-HT1D receptor. Other tryptamine derivatives displayed moderate binding for h5-HT1A and h5-HT1B receptors, along with Ki values ranging from 14-20 nM for the h5-HT1D sites. In addition, the syntheses of two alkylamino side chain restricted derivatives are described. 3-Amino-6-[[(trifluoromethyl)sulfonyl]oxy]-1,2,3,4-tetrahydrocarbazol e 21, as well as 4-[5-[[(trifluoromethyl)sulfonyl]oxy]-1H-indol-3-yl]piperidines 24 and 25, induced a shift in selectivity in favor of the h5-HT1B receptor. The relatively longer distance between the basic amine and a hydrogen-bond accepting oxygen in 21, 24 and 25 as compared to the non-restricted tryptamines, is likely responsible for this observation.</description><identifier>ISSN: 0968-0896</identifier><identifier>DOI: 10.1016/S0968-0896(98)00079-0</identifier><identifier>PMID: 9801818</identifier><language>eng</language><publisher>England</publisher><subject>Animals ; COS Cells ; Crystallography, X-Ray ; HeLa Cells ; Humans ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Protein Binding ; Receptor, Serotonin, 5-HT1B ; Receptor, Serotonin, 5-HT1D ; Receptors, Serotonin - metabolism ; Recombinant Proteins - metabolism ; Structure-Activity Relationship ; Tryptamines - chemistry ; Tryptamines - metabolism ; Tryptamines - pharmacology</subject><ispartof>Bioorganic & medicinal chemistry, 1998-09, Vol.6 (9), p.1469-1479</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9801818$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Barf, T</creatorcontrib><creatorcontrib>Wikström, H</creatorcontrib><creatorcontrib>Pauwels, P J</creatorcontrib><creatorcontrib>Palmier, C</creatorcontrib><creatorcontrib>Tardif, S</creatorcontrib><creatorcontrib>Lundmark, M</creatorcontrib><creatorcontrib>Sundell, S</creatorcontrib><title>5-(Sulfonyl)oxy-tryptamines and ethylamino side chain restricted derivatives. Structure-affinity relationships for h5-HT1B and h5-HT1D receptors</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A number of sulfonic acid ester derivatives of serotonin (5-hydroxytryptamine; 5-HT; 1) were prepared and their affinities are compared to that of the reference compound 5-[[(trifluoromethyl)sulfonyl]oxy]-tryptamine (8b). The structure-affinity relationship (SAFIR) is discussed in terms of in vitro binding for cloned human h5-HT1A, h5-HT1B and h5-HT1D receptors. All tryptamine derivatives exhibited the best affinities for h5-HT1D receptors but still, these were comparatively lower than that of compound 8b. 5-Tosylated tryptamine 11b (Ki = 6 nM) and the sulfamate derivatives 13b and 14b (Ki = 7 and 11 nM, respectively) were found to have the highest affinities for the h5-HT1D receptor. Other tryptamine derivatives displayed moderate binding for h5-HT1A and h5-HT1B receptors, along with Ki values ranging from 14-20 nM for the h5-HT1D sites. In addition, the syntheses of two alkylamino side chain restricted derivatives are described. 3-Amino-6-[[(trifluoromethyl)sulfonyl]oxy]-1,2,3,4-tetrahydrocarbazol e 21, as well as 4-[5-[[(trifluoromethyl)sulfonyl]oxy]-1H-indol-3-yl]piperidines 24 and 25, induced a shift in selectivity in favor of the h5-HT1B receptor. The relatively longer distance between the basic amine and a hydrogen-bond accepting oxygen in 21, 24 and 25 as compared to the non-restricted tryptamines, is likely responsible for this observation.</description><subject>Animals</subject><subject>COS Cells</subject><subject>Crystallography, X-Ray</subject><subject>HeLa Cells</subject><subject>Humans</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Mass Spectrometry</subject><subject>Protein Binding</subject><subject>Receptor, Serotonin, 5-HT1B</subject><subject>Receptor, Serotonin, 5-HT1D</subject><subject>Receptors, Serotonin - metabolism</subject><subject>Recombinant Proteins - metabolism</subject><subject>Structure-Activity Relationship</subject><subject>Tryptamines - chemistry</subject><subject>Tryptamines - metabolism</subject><subject>Tryptamines - pharmacology</subject><issn>0968-0896</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1998</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kM1OwzAQhH0AlVJ4hEo-ofbgYidxEh_5L1IlDi3nyIk3ilEaB9upyFvwyBhacdqdnU8jzSI0Z3TFKEtvt1SkOaG5SBciX1JKM0HoGZr-ny_QpXMfwYgSwSZoInLKcpZP0Tcni-3Q1qYb26X5Gom3Y-_lXnfgsOwUBt-M7a822GkFuGqk7rAF562uPCiswOqD9PoAboW33g6VHywQWde6034MaBtc07lG9w7XxuKGk_WO3f_FH_fHQFXQe2PdFTqvZevg-jRn6P35afewJpu3l9eHuw3pWZx7kiUASRpzVooyiiImIeE0TaKkUrHIeJyKspR5LHkWOMkhrQUvqVS0zhSoAM3QzTG3t-ZzCHWKvXYVtK3swAyuyChlIolEAOcncCj3oIre6r20Y3F6YfwDgdB0xQ</recordid><startdate>199809</startdate><enddate>199809</enddate><creator>Barf, T</creator><creator>Wikström, H</creator><creator>Pauwels, P J</creator><creator>Palmier, C</creator><creator>Tardif, S</creator><creator>Lundmark, M</creator><creator>Sundell, S</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>199809</creationdate><title>5-(Sulfonyl)oxy-tryptamines and ethylamino side chain restricted derivatives. Structure-affinity relationships for h5-HT1B and h5-HT1D receptors</title><author>Barf, T ; Wikström, H ; Pauwels, P J ; Palmier, C ; Tardif, S ; Lundmark, M ; Sundell, S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p138t-74ee46351b9b2221ae4506424cd3975369bba83a57ee4a5e6f95b0ad0f7dedcd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1998</creationdate><topic>Animals</topic><topic>COS Cells</topic><topic>Crystallography, X-Ray</topic><topic>HeLa Cells</topic><topic>Humans</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Mass Spectrometry</topic><topic>Protein Binding</topic><topic>Receptor, Serotonin, 5-HT1B</topic><topic>Receptor, Serotonin, 5-HT1D</topic><topic>Receptors, Serotonin - metabolism</topic><topic>Recombinant Proteins - metabolism</topic><topic>Structure-Activity Relationship</topic><topic>Tryptamines - chemistry</topic><topic>Tryptamines - metabolism</topic><topic>Tryptamines - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Barf, T</creatorcontrib><creatorcontrib>Wikström, H</creatorcontrib><creatorcontrib>Pauwels, P J</creatorcontrib><creatorcontrib>Palmier, C</creatorcontrib><creatorcontrib>Tardif, S</creatorcontrib><creatorcontrib>Lundmark, M</creatorcontrib><creatorcontrib>Sundell, S</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Barf, T</au><au>Wikström, H</au><au>Pauwels, P J</au><au>Palmier, C</au><au>Tardif, S</au><au>Lundmark, M</au><au>Sundell, S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>5-(Sulfonyl)oxy-tryptamines and ethylamino side chain restricted derivatives. Structure-affinity relationships for h5-HT1B and h5-HT1D receptors</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>1998-09</date><risdate>1998</risdate><volume>6</volume><issue>9</issue><spage>1469</spage><epage>1479</epage><pages>1469-1479</pages><issn>0968-0896</issn><abstract>A number of sulfonic acid ester derivatives of serotonin (5-hydroxytryptamine; 5-HT; 1) were prepared and their affinities are compared to that of the reference compound 5-[[(trifluoromethyl)sulfonyl]oxy]-tryptamine (8b). The structure-affinity relationship (SAFIR) is discussed in terms of in vitro binding for cloned human h5-HT1A, h5-HT1B and h5-HT1D receptors. All tryptamine derivatives exhibited the best affinities for h5-HT1D receptors but still, these were comparatively lower than that of compound 8b. 5-Tosylated tryptamine 11b (Ki = 6 nM) and the sulfamate derivatives 13b and 14b (Ki = 7 and 11 nM, respectively) were found to have the highest affinities for the h5-HT1D receptor. Other tryptamine derivatives displayed moderate binding for h5-HT1A and h5-HT1B receptors, along with Ki values ranging from 14-20 nM for the h5-HT1D sites. In addition, the syntheses of two alkylamino side chain restricted derivatives are described. 3-Amino-6-[[(trifluoromethyl)sulfonyl]oxy]-1,2,3,4-tetrahydrocarbazol e 21, as well as 4-[5-[[(trifluoromethyl)sulfonyl]oxy]-1H-indol-3-yl]piperidines 24 and 25, induced a shift in selectivity in favor of the h5-HT1B receptor. The relatively longer distance between the basic amine and a hydrogen-bond accepting oxygen in 21, 24 and 25 as compared to the non-restricted tryptamines, is likely responsible for this observation.</abstract><cop>England</cop><pmid>9801818</pmid><doi>10.1016/S0968-0896(98)00079-0</doi><tpages>11</tpages></addata></record> |
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| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 1998-09, Vol.6 (9), p.1469-1479 |
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| subjects | Animals COS Cells Crystallography, X-Ray HeLa Cells Humans Magnetic Resonance Spectroscopy Mass Spectrometry Protein Binding Receptor, Serotonin, 5-HT1B Receptor, Serotonin, 5-HT1D Receptors, Serotonin - metabolism Recombinant Proteins - metabolism Structure-Activity Relationship Tryptamines - chemistry Tryptamines - metabolism Tryptamines - pharmacology |
| title | 5-(Sulfonyl)oxy-tryptamines and ethylamino side chain restricted derivatives. Structure-affinity relationships for h5-HT1B and h5-HT1D receptors |
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