Histamine H1 receptor ligands. Part II. Synthesis and in vitro pharmacology of 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives
New 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives were prepared and tested in vitro as H1 receptor antagonists. The compounds with 2-phenylamino substitution with meta-halide substituents at the phenyl ring, showed weak H1-antagonistic activity (pA2...
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| Veröffentlicht in: | Farmaco (Società chimica italiana : 1989) 2000-09, Vol.55 (9-10), p.569-574 |
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| container_issue | 9-10 |
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| container_title | Farmaco (Società chimica italiana : 1989) |
| container_volume | 55 |
| creator | WALCZYNSKI, Krzysztof GURYN, Roman ZUIDERVELD, Obbe P ZHANG, Ming-Qiang TIMMERMAN, Henk |
| description | New 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives were prepared and tested in vitro as H1 receptor antagonists. The compounds with 2-phenylamino substitution with meta-halide substituents at the phenyl ring, showed weak H1-antagonistic activity (pA2: 4.62-5.04) and this activity was completely lost in the case of meta-methyl substituent (pA2 < 4). When the phenylamino group was replaced by benzhydryl groups of classic antihistamines, the resulting compounds exhibited slightly improved H1-antagonistic activity (at the meta-position pA2: 6.38-6.15; at the para-position pA2: 6.04-5.87). |
| doi_str_mv | 10.1016/S0014-827X(00)00087-2 |
| format | Article |
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When the phenylamino group was replaced by benzhydryl groups of classic antihistamines, the resulting compounds exhibited slightly improved H1-antagonistic activity (at the meta-position pA2: 6.38-6.15; at the para-position pA2: 6.04-5.87).</description><identifier>ISSN: 0014-827X</identifier><identifier>EISSN: 1879-0569</identifier><identifier>DOI: 10.1016/S0014-827X(00)00087-2</identifier><identifier>PMID: 11152236</identifier><language>eng</language><publisher>Lausanne: Elsevier Science</publisher><subject>Animals ; Biological and medical sciences ; Ethylamines - chemical synthesis ; Ethylamines - chemistry ; Ethylamines - pharmacology ; Guinea Pigs ; Histamine and antagonists. Allergy ; Histamine Antagonists - chemical synthesis ; Histamine Antagonists - chemistry ; Histamine Antagonists - pharmacology ; Ligands ; Male ; Medical sciences ; Molecular Structure ; Pharmacology. Drug treatments ; Receptors, Histamine H1 - metabolism ; Thiazoles - chemical synthesis ; Thiazoles - chemistry ; Thiazoles - pharmacology</subject><ispartof>Farmaco (Società chimica italiana : 1989), 2000-09, Vol.55 (9-10), p.569-574</ispartof><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=815592$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11152236$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>WALCZYNSKI, Krzysztof</creatorcontrib><creatorcontrib>GURYN, Roman</creatorcontrib><creatorcontrib>ZUIDERVELD, Obbe P</creatorcontrib><creatorcontrib>ZHANG, Ming-Qiang</creatorcontrib><creatorcontrib>TIMMERMAN, Henk</creatorcontrib><title>Histamine H1 receptor ligands. Part II. Synthesis and in vitro pharmacology of 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives</title><title>Farmaco (Società chimica italiana : 1989)</title><addtitle>Farmaco</addtitle><description>New 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives were prepared and tested in vitro as H1 receptor antagonists. The compounds with 2-phenylamino substitution with meta-halide substituents at the phenyl ring, showed weak H1-antagonistic activity (pA2: 4.62-5.04) and this activity was completely lost in the case of meta-methyl substituent (pA2 < 4). When the phenylamino group was replaced by benzhydryl groups of classic antihistamines, the resulting compounds exhibited slightly improved H1-antagonistic activity (at the meta-position pA2: 6.38-6.15; at the para-position pA2: 6.04-5.87).</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Ethylamines - chemical synthesis</subject><subject>Ethylamines - chemistry</subject><subject>Ethylamines - pharmacology</subject><subject>Guinea Pigs</subject><subject>Histamine and antagonists. Allergy</subject><subject>Histamine Antagonists - chemical synthesis</subject><subject>Histamine Antagonists - chemistry</subject><subject>Histamine Antagonists - pharmacology</subject><subject>Ligands</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Pharmacology. Drug treatments</subject><subject>Receptors, Histamine H1 - metabolism</subject><subject>Thiazoles - chemical synthesis</subject><subject>Thiazoles - chemistry</subject><subject>Thiazoles - pharmacology</subject><issn>0014-827X</issn><issn>1879-0569</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpN0NGK1DAUBuAgijuuPoISEGTnImOSNk17KYs6AwsKqyCIDKfp6TaSJjXJDHRfyle0y47LXh0O5-M_8BPyWvCN4KJ6f825KFkt9Y8Lztec81oz-YSsRK0bxlXVPCWrB3JGXqT0e1m1rvRzciaEUFIW1Yr83dqUYbQe6VbQiAanHCJ19gZ8lzb0K8RMd7sNvZ59HjDZRJcDtZ4ebY6BTgPEEUxw4WamoaeS_ZTsYhrQz-4uNqzzYOE2OFay2f3CPIC_f3cXs1DJWvS3w9zF2T2m60e0w2iPkO0R00vyrAeX8NVpnpPvnz5-u9yyqy-fd5cfrtgkFM-sbEpetAi9ksJIwKYTomu1BM0NGi6b3pS1rrDSpgZjKiELWetat0Wllpqa4py8u8-dYvhzwJT3o00GnQOP4ZD2WqpCCaEX-OYED-2I3X6KdoQ47_9XvIC3JwDJgOsjeGPTg6uFUo0s_gGA3Y0G</recordid><startdate>200009</startdate><enddate>200009</enddate><creator>WALCZYNSKI, Krzysztof</creator><creator>GURYN, Roman</creator><creator>ZUIDERVELD, Obbe P</creator><creator>ZHANG, Ming-Qiang</creator><creator>TIMMERMAN, Henk</creator><general>Elsevier Science</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>200009</creationdate><title>Histamine H1 receptor ligands. Part II. Synthesis and in vitro pharmacology of 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives</title><author>WALCZYNSKI, Krzysztof ; GURYN, Roman ; ZUIDERVELD, Obbe P ; ZHANG, Ming-Qiang ; TIMMERMAN, Henk</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p150t-49403beaf521c2ae9d11db72a70cec029fc4876e67c8acc612328787b36500193</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Ethylamines - chemical synthesis</topic><topic>Ethylamines - chemistry</topic><topic>Ethylamines - pharmacology</topic><topic>Guinea Pigs</topic><topic>Histamine and antagonists. Allergy</topic><topic>Histamine Antagonists - chemical synthesis</topic><topic>Histamine Antagonists - chemistry</topic><topic>Histamine Antagonists - pharmacology</topic><topic>Ligands</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Pharmacology. Drug treatments</topic><topic>Receptors, Histamine H1 - metabolism</topic><topic>Thiazoles - chemical synthesis</topic><topic>Thiazoles - chemistry</topic><topic>Thiazoles - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>WALCZYNSKI, Krzysztof</creatorcontrib><creatorcontrib>GURYN, Roman</creatorcontrib><creatorcontrib>ZUIDERVELD, Obbe P</creatorcontrib><creatorcontrib>ZHANG, Ming-Qiang</creatorcontrib><creatorcontrib>TIMMERMAN, Henk</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Farmaco (Società chimica italiana : 1989)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>WALCZYNSKI, Krzysztof</au><au>GURYN, Roman</au><au>ZUIDERVELD, Obbe P</au><au>ZHANG, Ming-Qiang</au><au>TIMMERMAN, Henk</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Histamine H1 receptor ligands. 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| ispartof | Farmaco (Società chimica italiana : 1989), 2000-09, Vol.55 (9-10), p.569-574 |
| issn | 0014-827X 1879-0569 |
| language | eng |
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| source | MEDLINE; Alma/SFX Local Collection |
| subjects | Animals Biological and medical sciences Ethylamines - chemical synthesis Ethylamines - chemistry Ethylamines - pharmacology Guinea Pigs Histamine and antagonists. Allergy Histamine Antagonists - chemical synthesis Histamine Antagonists - chemistry Histamine Antagonists - pharmacology Ligands Male Medical sciences Molecular Structure Pharmacology. Drug treatments Receptors, Histamine H1 - metabolism Thiazoles - chemical synthesis Thiazoles - chemistry Thiazoles - pharmacology |
| title | Histamine H1 receptor ligands. Part II. Synthesis and in vitro pharmacology of 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives |
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