Synthesis, Ionotropic Glutamate Receptor Binding Affinity, and Structure−Activity Relationships of a New Set of 4,5-Dihydro-8-heteroaryl-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates Analogues of TQX-173
A series of 4,5-dihydro-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates analogues of TQX-173 (1b), bearing different nitrogen-containing heterocycles at position-8, were synthesized as AMPA receptor antagonists. All the reported compounds were also biologically evaluated for their binding at g...
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| Veröffentlicht in: | Journal of medicinal chemistry 2001-09, Vol.44 (19), p.3157-3165 |
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| container_title | Journal of medicinal chemistry |
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| creator | Catarzi, Daniela Colotta, Vittoria Varano, Flavia Filacchioni, Guido Galli, Alessandro Costagli, Chiara Carlà, Vincenzo |
| description | A series of 4,5-dihydro-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates analogues of TQX-173 (1b), bearing different nitrogen-containing heterocycles at position-8, were synthesized as AMPA receptor antagonists. All the reported compounds were also biologically evaluated for their binding at glycine/NMDA and KA receptors to better assess their selectivity toward the AMPA receptor. Structure−activity relationships (SAR) on these TQX derivatives have evidenced that the precise positioning of the nitrogen atoms and the specific electronic topography of the 8-heteroaromatic ring are both important for the anchoring to the AMPA receptor. In fact, it has been well-established that the presence of a N3-nitrogen-containing heterocycle at position-8 of the TQX framework is an essential feature for potent and selective AMPA receptor antagonists. Functional antagonism at both AMPA receptor and NMDA receptor-ion channel complex was evaluated by assessing the ability of some selected compounds to inhibit depolarization induced by 5 μM AMPA or NMDA in mouse cortical wedge preparations. |
| doi_str_mv | 10.1021/jm010862q |
| format | Article |
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All the reported compounds were also biologically evaluated for their binding at glycine/NMDA and KA receptors to better assess their selectivity toward the AMPA receptor. Structure−activity relationships (SAR) on these TQX derivatives have evidenced that the precise positioning of the nitrogen atoms and the specific electronic topography of the 8-heteroaromatic ring are both important for the anchoring to the AMPA receptor. In fact, it has been well-established that the presence of a N3-nitrogen-containing heterocycle at position-8 of the TQX framework is an essential feature for potent and selective AMPA receptor antagonists. Functional antagonism at both AMPA receptor and NMDA receptor-ion channel complex was evaluated by assessing the ability of some selected compounds to inhibit depolarization induced by 5 μM AMPA or NMDA in mouse cortical wedge preparations.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm010862q</identifier><identifier>PMID: 11543685</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid - antagonists & inhibitors ; alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid - metabolism ; Animals ; Biological and medical sciences ; Cerebral Cortex - metabolism ; Cerebral Cortex - physiology ; Cerebral Cortex - ultrastructure ; Electrophysiology ; Excitatory Amino Acid Antagonists - chemical synthesis ; Excitatory Amino Acid Antagonists - chemistry ; Excitatory Amino Acid Antagonists - metabolism ; Excitatory Amino Acid Antagonists - pharmacology ; Glutamatergic system (aspartate and other excitatory aminoacids) ; In Vitro Techniques ; Ligands ; Male ; Medical sciences ; Mice ; N-Methylaspartate - antagonists & inhibitors ; N-Methylaspartate - metabolism ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Pharmacology. Drug treatments ; Quinoxalines - chemical synthesis ; Quinoxalines - chemistry ; Quinoxalines - metabolism ; Quinoxalines - pharmacology ; Rats ; Receptors, Glutamate - drug effects ; Receptors, Glutamate - metabolism ; Receptors, Kainic Acid - antagonists & inhibitors ; Receptors, Kainic Acid - metabolism ; Structure-Activity Relationship ; Synaptic Membranes - metabolism ; Triazines - chemical synthesis ; Triazines - chemistry ; Triazines - metabolism ; Triazines - pharmacology</subject><ispartof>Journal of medicinal chemistry, 2001-09, Vol.44 (19), p.3157-3165</ispartof><rights>Copyright © 2001 American Chemical Society</rights><rights>2002 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-61f6c8416da6b387a38d21885b21eaf1dead29edf12401302e45115c4b6905ad3</citedby><cites>FETCH-LOGICAL-a379t-61f6c8416da6b387a38d21885b21eaf1dead29edf12401302e45115c4b6905ad3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm010862q$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm010862q$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14060133$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11543685$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Catarzi, Daniela</creatorcontrib><creatorcontrib>Colotta, Vittoria</creatorcontrib><creatorcontrib>Varano, Flavia</creatorcontrib><creatorcontrib>Filacchioni, Guido</creatorcontrib><creatorcontrib>Galli, Alessandro</creatorcontrib><creatorcontrib>Costagli, Chiara</creatorcontrib><creatorcontrib>Carlà, Vincenzo</creatorcontrib><title>Synthesis, Ionotropic Glutamate Receptor Binding Affinity, and Structure−Activity Relationships of a New Set of 4,5-Dihydro-8-heteroaryl-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates Analogues of TQX-173</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A series of 4,5-dihydro-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates analogues of TQX-173 (1b), bearing different nitrogen-containing heterocycles at position-8, were synthesized as AMPA receptor antagonists. All the reported compounds were also biologically evaluated for their binding at glycine/NMDA and KA receptors to better assess their selectivity toward the AMPA receptor. Structure−activity relationships (SAR) on these TQX derivatives have evidenced that the precise positioning of the nitrogen atoms and the specific electronic topography of the 8-heteroaromatic ring are both important for the anchoring to the AMPA receptor. In fact, it has been well-established that the presence of a N3-nitrogen-containing heterocycle at position-8 of the TQX framework is an essential feature for potent and selective AMPA receptor antagonists. Functional antagonism at both AMPA receptor and NMDA receptor-ion channel complex was evaluated by assessing the ability of some selected compounds to inhibit depolarization induced by 5 μM AMPA or NMDA in mouse cortical wedge preparations.</description><subject>alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid - antagonists & inhibitors</subject><subject>alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid - metabolism</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cerebral Cortex - metabolism</subject><subject>Cerebral Cortex - physiology</subject><subject>Cerebral Cortex - ultrastructure</subject><subject>Electrophysiology</subject><subject>Excitatory Amino Acid Antagonists - chemical synthesis</subject><subject>Excitatory Amino Acid Antagonists - chemistry</subject><subject>Excitatory Amino Acid Antagonists - metabolism</subject><subject>Excitatory Amino Acid Antagonists - pharmacology</subject><subject>Glutamatergic system (aspartate and other excitatory aminoacids)</subject><subject>In Vitro Techniques</subject><subject>Ligands</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>N-Methylaspartate - antagonists & inhibitors</subject><subject>N-Methylaspartate - metabolism</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Pharmacology. Drug treatments</subject><subject>Quinoxalines - chemical synthesis</subject><subject>Quinoxalines - chemistry</subject><subject>Quinoxalines - metabolism</subject><subject>Quinoxalines - pharmacology</subject><subject>Rats</subject><subject>Receptors, Glutamate - drug effects</subject><subject>Receptors, Glutamate - metabolism</subject><subject>Receptors, Kainic Acid - antagonists & inhibitors</subject><subject>Receptors, Kainic Acid - metabolism</subject><subject>Structure-Activity Relationship</subject><subject>Synaptic Membranes - metabolism</subject><subject>Triazines - chemical synthesis</subject><subject>Triazines - chemistry</subject><subject>Triazines - metabolism</subject><subject>Triazines - pharmacology</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkUuOEzEQhlsIxISBBRdA3oCE1Aa_2t1ZhsA8pBGPSUBICLUqbvfEmY6d2G5IOAFr7sYFOAkeEk02rEql-vzX7_qz7DElLyhh9OViSSipJFvfyQa0YASLioi72YAQxjCTjB9lD0JYEEI4Zfx-dkRpIbisikH2e7K1ca6DCTk6d9ZF71ZGodOuj7CEqNGlVnoVnUevjG2MvUKjtjXWxG2OwDZoEn2vYu_1n5-_Riqab2mS3nQQjbNhblYBuRYBequ_o4mON43IC_zazLeNd7jCcx21d-C3HRbYbRymOcsFjt7AD9e5LzTR8HXdG-s20BmrMcMK_MxttmmJDmhkoXNXvf63aPrhM6Ylf5jda6EL-tG-HmcfT95Mx2f44t3p-Xh0gYGXw4glbaWqBJUNyBmvSuBVw2hVFTNGNbS00dCwoW5aygShnDAtinQ6JWZySApo-HH2bKe78m6dLMR6aYLSXQdWuz7UJaWiKAuSwOc7UHkXgtdtvfJmmX5dU1LfZFjfZpjYJ3vRfrbUzYHch5aAp3sAgoKu9WCVCQdOEJnc8sThHWdC1JvbOfjrWpa8LOrp-0l9-WlyRtn4pJYHXVChXrjep8uG_xj8CxelwTE</recordid><startdate>20010913</startdate><enddate>20010913</enddate><creator>Catarzi, Daniela</creator><creator>Colotta, Vittoria</creator><creator>Varano, Flavia</creator><creator>Filacchioni, Guido</creator><creator>Galli, Alessandro</creator><creator>Costagli, Chiara</creator><creator>Carlà, Vincenzo</creator><general>American Chemical Society</general><scope>BSCLL</scope><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>20010913</creationdate><title>Synthesis, Ionotropic Glutamate Receptor Binding Affinity, and Structure−Activity Relationships of a New Set of 4,5-Dihydro-8-heteroaryl-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates Analogues of TQX-173</title><author>Catarzi, Daniela ; Colotta, Vittoria ; Varano, Flavia ; Filacchioni, Guido ; Galli, Alessandro ; Costagli, Chiara ; Carlà, Vincenzo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-61f6c8416da6b387a38d21885b21eaf1dead29edf12401302e45115c4b6905ad3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid - antagonists & inhibitors</topic><topic>alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid - metabolism</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Cerebral Cortex - metabolism</topic><topic>Cerebral Cortex - physiology</topic><topic>Cerebral Cortex - ultrastructure</topic><topic>Electrophysiology</topic><topic>Excitatory Amino Acid Antagonists - chemical synthesis</topic><topic>Excitatory Amino Acid Antagonists - chemistry</topic><topic>Excitatory Amino Acid Antagonists - metabolism</topic><topic>Excitatory Amino Acid Antagonists - pharmacology</topic><topic>Glutamatergic system (aspartate and other excitatory aminoacids)</topic><topic>In Vitro Techniques</topic><topic>Ligands</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>N-Methylaspartate - antagonists & inhibitors</topic><topic>N-Methylaspartate - metabolism</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Pharmacology. Drug treatments</topic><topic>Quinoxalines - chemical synthesis</topic><topic>Quinoxalines - chemistry</topic><topic>Quinoxalines - metabolism</topic><topic>Quinoxalines - pharmacology</topic><topic>Rats</topic><topic>Receptors, Glutamate - drug effects</topic><topic>Receptors, Glutamate - metabolism</topic><topic>Receptors, Kainic Acid - antagonists & inhibitors</topic><topic>Receptors, Kainic Acid - metabolism</topic><topic>Structure-Activity Relationship</topic><topic>Synaptic Membranes - metabolism</topic><topic>Triazines - chemical synthesis</topic><topic>Triazines - chemistry</topic><topic>Triazines - metabolism</topic><topic>Triazines - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Catarzi, Daniela</creatorcontrib><creatorcontrib>Colotta, Vittoria</creatorcontrib><creatorcontrib>Varano, Flavia</creatorcontrib><creatorcontrib>Filacchioni, Guido</creatorcontrib><creatorcontrib>Galli, Alessandro</creatorcontrib><creatorcontrib>Costagli, Chiara</creatorcontrib><creatorcontrib>Carlà, Vincenzo</creatorcontrib><collection>Istex</collection><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>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Catarzi, Daniela</au><au>Colotta, Vittoria</au><au>Varano, Flavia</au><au>Filacchioni, Guido</au><au>Galli, Alessandro</au><au>Costagli, Chiara</au><au>Carlà, Vincenzo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, Ionotropic Glutamate Receptor Binding Affinity, and Structure−Activity Relationships of a New Set of 4,5-Dihydro-8-heteroaryl-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates Analogues of TQX-173</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2001-09-13</date><risdate>2001</risdate><volume>44</volume><issue>19</issue><spage>3157</spage><epage>3165</epage><pages>3157-3165</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>A series of 4,5-dihydro-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates analogues of TQX-173 (1b), bearing different nitrogen-containing heterocycles at position-8, were synthesized as AMPA receptor antagonists. All the reported compounds were also biologically evaluated for their binding at glycine/NMDA and KA receptors to better assess their selectivity toward the AMPA receptor. Structure−activity relationships (SAR) on these TQX derivatives have evidenced that the precise positioning of the nitrogen atoms and the specific electronic topography of the 8-heteroaromatic ring are both important for the anchoring to the AMPA receptor. In fact, it has been well-established that the presence of a N3-nitrogen-containing heterocycle at position-8 of the TQX framework is an essential feature for potent and selective AMPA receptor antagonists. Functional antagonism at both AMPA receptor and NMDA receptor-ion channel complex was evaluated by assessing the ability of some selected compounds to inhibit depolarization induced by 5 μM AMPA or NMDA in mouse cortical wedge preparations.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>11543685</pmid><doi>10.1021/jm010862q</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Journal of medicinal chemistry, 2001-09, Vol.44 (19), p.3157-3165 |
| issn | 0022-2623 1520-4804 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid - antagonists & inhibitors alpha-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid - metabolism Animals Biological and medical sciences Cerebral Cortex - metabolism Cerebral Cortex - physiology Cerebral Cortex - ultrastructure Electrophysiology Excitatory Amino Acid Antagonists - chemical synthesis Excitatory Amino Acid Antagonists - chemistry Excitatory Amino Acid Antagonists - metabolism Excitatory Amino Acid Antagonists - pharmacology Glutamatergic system (aspartate and other excitatory aminoacids) In Vitro Techniques Ligands Male Medical sciences Mice N-Methylaspartate - antagonists & inhibitors N-Methylaspartate - metabolism Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Pharmacology. Drug treatments Quinoxalines - chemical synthesis Quinoxalines - chemistry Quinoxalines - metabolism Quinoxalines - pharmacology Rats Receptors, Glutamate - drug effects Receptors, Glutamate - metabolism Receptors, Kainic Acid - antagonists & inhibitors Receptors, Kainic Acid - metabolism Structure-Activity Relationship Synaptic Membranes - metabolism Triazines - chemical synthesis Triazines - chemistry Triazines - metabolism Triazines - pharmacology |
| title | Synthesis, Ionotropic Glutamate Receptor Binding Affinity, and Structure−Activity Relationships of a New Set of 4,5-Dihydro-8-heteroaryl-4-oxo-1,2,4-triazolo[1,5-a]quinoxaline-2-carboxylates Analogues of TQX-173 |
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