Novel bradykinin-1 antagonists containing a (1,2,3,4-tetrahydro-isoquinolin-1-yl)acetic acid scaffold
A novel B 1 antagonist core was utilized and the effects of modification of its amide side chain on the biological activity were tested. The imino functional group of isoquinolin-1-ylacetic acid and its 6,7-dimethoxy variant was sulfonylated (4-toluenesulfonyl), while the acetyl side chain was conve...
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| Veröffentlicht in: | European journal of medicinal chemistry 2008-07, Vol.43 (7), p.1552-1558 |
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| container_issue | 7 |
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| container_title | European journal of medicinal chemistry |
| container_volume | 43 |
| creator | Huszár, József Timár, Zoltán Szalai, Krisztina Katalin Keserű, György Fülöp, Ferenc Penke, Botond |
| description | A novel B
1 antagonist core was utilized and the effects of modification of its amide side chain on the biological activity were tested. The imino functional group of isoquinolin-1-ylacetic acid and its 6,7-dimethoxy variant was sulfonylated (4-toluenesulfonyl), while the acetyl side chain was converted to amides. Three of the synthesized compounds exhibited significant activity at the recombinant human B
1 receptors in binding tests and also in a functional assay.
Novel B
1 antagonist core 1,2,3,4-tetrahydroisoquinolin-1-ylacetic acid was utilized and the effect of modification of its amide side chain on the biological activity was tested.
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| doi_str_mv | 10.1016/j.ejmech.2007.10.030 |
| format | Article |
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1 antagonist core was utilized and the effects of modification of its amide side chain on the biological activity were tested. The imino functional group of isoquinolin-1-ylacetic acid and its 6,7-dimethoxy variant was sulfonylated (4-toluenesulfonyl), while the acetyl side chain was converted to amides. Three of the synthesized compounds exhibited significant activity at the recombinant human B
1 receptors in binding tests and also in a functional assay.
Novel B
1 antagonist core 1,2,3,4-tetrahydroisoquinolin-1-ylacetic acid was utilized and the effect of modification of its amide side chain on the biological activity was tested.
[Display omitted]</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2007.10.030</identifier><identifier>PMID: 18068274</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Oxford: Elsevier Masson SAS</publisher><subject>B 1 antagonist ; Biological and medical sciences ; Bradykinin ; Bradykinin Receptor Antagonists ; Bradykinin-1 receptor ; Calcium - metabolism ; Cytoplasm - metabolism ; Fluorometry ; Isoquinoline ; Magnetic Resonance Spectroscopy ; Medical sciences ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems ; Peptidomimetic ; Pharmacology. Drug treatments ; Spectrometry, Mass, Electrospray Ionization ; Tetrahydroisoquinolines - chemistry ; Tetrahydroisoquinolines - pharmacology</subject><ispartof>European journal of medicinal chemistry, 2008-07, Vol.43 (7), p.1552-1558</ispartof><rights>2007 Elsevier Masson SAS</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-aa395cbf72a077c9117b2975491bd02c5727cf496e798e33666a1f4f8c78d0c13</citedby><cites>FETCH-LOGICAL-c390t-aa395cbf72a077c9117b2975491bd02c5727cf496e798e33666a1f4f8c78d0c13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0223523407004102$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20525339$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18068274$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Huszár, József</creatorcontrib><creatorcontrib>Timár, Zoltán</creatorcontrib><creatorcontrib>Szalai, Krisztina Katalin</creatorcontrib><creatorcontrib>Keserű, György</creatorcontrib><creatorcontrib>Fülöp, Ferenc</creatorcontrib><creatorcontrib>Penke, Botond</creatorcontrib><title>Novel bradykinin-1 antagonists containing a (1,2,3,4-tetrahydro-isoquinolin-1-yl)acetic acid scaffold</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>A novel B
1 antagonist core was utilized and the effects of modification of its amide side chain on the biological activity were tested. The imino functional group of isoquinolin-1-ylacetic acid and its 6,7-dimethoxy variant was sulfonylated (4-toluenesulfonyl), while the acetyl side chain was converted to amides. Three of the synthesized compounds exhibited significant activity at the recombinant human B
1 receptors in binding tests and also in a functional assay.
Novel B
1 antagonist core 1,2,3,4-tetrahydroisoquinolin-1-ylacetic acid was utilized and the effect of modification of its amide side chain on the biological activity was tested.
[Display omitted]</description><subject>B 1 antagonist</subject><subject>Biological and medical sciences</subject><subject>Bradykinin</subject><subject>Bradykinin Receptor Antagonists</subject><subject>Bradykinin-1 receptor</subject><subject>Calcium - metabolism</subject><subject>Cytoplasm - metabolism</subject><subject>Fluorometry</subject><subject>Isoquinoline</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</subject><subject>Peptidomimetic</subject><subject>Pharmacology. Drug treatments</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Tetrahydroisoquinolines - chemistry</subject><subject>Tetrahydroisoquinolines - pharmacology</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMFu1DAQhi0EokvhDRDKBQTSehnbiZ1cKqEKSqWqXOBsOeNJ6yUbFztbad8eR7uCW0-Wf33_aOZj7K2AjQChP283tN0R3m8kgCnRBhQ8YythdMuVbOrnbAVSKt5IVZ-xVzlvAaDRAC_ZmWhBt9LUK0a38ZHGqk_OH36HKUxcVG6a3V2cQp5zhbF8lvyuctVHsZZrta75THNy9wefIg85_tmHKY5LlR_GTw5pDlg5DL7K6IYhjv41ezG4MdOb03vOfn37-vPyO7_5cXV9-eWGo-pg5s6prsF-MNKBMdgJYXrZmabuRO9BYmOkwaHuNJmuJaW01k4M9dCiaT2gUOfsw3HuQypbUZ7tLmSkcXQTxX22upOmNVIXsD6CmGLOiQb7kMLOpYMVYBe9dmuPeu2id0mL3lJ7d5q_73fk_5dOPgvw_gS4cvs4JDdhyP84CY1slOoKd3HkqNh4DJRsxkATkg-JcLY-hqc3-Qu89Jkc</recordid><startdate>20080701</startdate><enddate>20080701</enddate><creator>Huszár, József</creator><creator>Timár, Zoltán</creator><creator>Szalai, Krisztina Katalin</creator><creator>Keserű, György</creator><creator>Fülöp, Ferenc</creator><creator>Penke, Botond</creator><general>Elsevier Masson SAS</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20080701</creationdate><title>Novel bradykinin-1 antagonists containing a (1,2,3,4-tetrahydro-isoquinolin-1-yl)acetic acid scaffold</title><author>Huszár, József ; Timár, Zoltán ; Szalai, Krisztina Katalin ; Keserű, György ; Fülöp, Ferenc ; Penke, Botond</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-aa395cbf72a077c9117b2975491bd02c5727cf496e798e33666a1f4f8c78d0c13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>B 1 antagonist</topic><topic>Biological and medical sciences</topic><topic>Bradykinin</topic><topic>Bradykinin Receptor Antagonists</topic><topic>Bradykinin-1 receptor</topic><topic>Calcium - metabolism</topic><topic>Cytoplasm - metabolism</topic><topic>Fluorometry</topic><topic>Isoquinoline</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</topic><topic>Peptidomimetic</topic><topic>Pharmacology. Drug treatments</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Tetrahydroisoquinolines - chemistry</topic><topic>Tetrahydroisoquinolines - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huszár, József</creatorcontrib><creatorcontrib>Timár, Zoltán</creatorcontrib><creatorcontrib>Szalai, Krisztina Katalin</creatorcontrib><creatorcontrib>Keserű, György</creatorcontrib><creatorcontrib>Fülöp, Ferenc</creatorcontrib><creatorcontrib>Penke, Botond</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>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Huszár, József</au><au>Timár, Zoltán</au><au>Szalai, Krisztina Katalin</au><au>Keserű, György</au><au>Fülöp, Ferenc</au><au>Penke, Botond</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel bradykinin-1 antagonists containing a (1,2,3,4-tetrahydro-isoquinolin-1-yl)acetic acid scaffold</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2008-07-01</date><risdate>2008</risdate><volume>43</volume><issue>7</issue><spage>1552</spage><epage>1558</epage><pages>1552-1558</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>A novel B
1 antagonist core was utilized and the effects of modification of its amide side chain on the biological activity were tested. The imino functional group of isoquinolin-1-ylacetic acid and its 6,7-dimethoxy variant was sulfonylated (4-toluenesulfonyl), while the acetyl side chain was converted to amides. Three of the synthesized compounds exhibited significant activity at the recombinant human B
1 receptors in binding tests and also in a functional assay.
Novel B
1 antagonist core 1,2,3,4-tetrahydroisoquinolin-1-ylacetic acid was utilized and the effect of modification of its amide side chain on the biological activity was tested.
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| subjects | B 1 antagonist Biological and medical sciences Bradykinin Bradykinin Receptor Antagonists Bradykinin-1 receptor Calcium - metabolism Cytoplasm - metabolism Fluorometry Isoquinoline Magnetic Resonance Spectroscopy Medical sciences Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems Peptidomimetic Pharmacology. Drug treatments Spectrometry, Mass, Electrospray Ionization Tetrahydroisoquinolines - chemistry Tetrahydroisoquinolines - pharmacology |
| title | Novel bradykinin-1 antagonists containing a (1,2,3,4-tetrahydro-isoquinolin-1-yl)acetic acid scaffold |
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