Selective NR1/2B N-Methyl-d-aspartate Receptor Antagonists among Indole-2-carboxamides and Benzimidazole-2-carboxamides
(4-Benzylpiperidine-1-yl)-(6-hydroxy-1H-indole-2-yl)-methanone (6a) derived from (E)-1-(4-benzylpiperidin-1-yl)-3-(4-hydroxy-phenyl)-propenone (5) was identified as a potent NR2B subunit-selective antagonist of the NMDA receptor. To establish the structure−activity relationship (SAR) and to attempt...
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| Veröffentlicht in: | Journal of medicinal chemistry 2007-03, Vol.50 (5), p.901-914 |
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| creator | Borza, István Bozó, Éva Barta-Szalai, Gizella Kiss, Csilla Tárkányi, Gábor Demeter, Ádám Gáti, Tamás Háda, Viktor Kolok, Sándor Gere, Anikó Fodor, László Nagy, József Galgóczy, Kornél Magdó, Ildikó Ágai, Béla Fetter, József Bertha, Ferenc Keserü, György M Horváth, Csilla Farkas, Sándor Greiner, István Domány, György |
| description | (4-Benzylpiperidine-1-yl)-(6-hydroxy-1H-indole-2-yl)-methanone (6a) derived from (E)-1-(4-benzylpiperidin-1-yl)-3-(4-hydroxy-phenyl)-propenone (5) was identified as a potent NR2B subunit-selective antagonist of the NMDA receptor. To establish the structure−activity relationship (SAR) and to attempt the improvement of the ADME properties of the lead, a series of compounds were prepared and tested. Several derivatives showed low nanomolar activity both in the binding and in the functional assay. In a formalin-induced hyperalgesia model in mice, 6a and (4-benzylpiperidine-1-yl)-[5(6)-hydroxy-1H-benzimidazol-2-yl]-methanone (60a) were as active as besonprodil (2) after oral administration. A CoMSIA model was developed based on binding data of a series of indole- and benzimidazole-2-carboxamides. |
| doi_str_mv | 10.1021/jm060420k |
| format | Article |
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To establish the structure−activity relationship (SAR) and to attempt the improvement of the ADME properties of the lead, a series of compounds were prepared and tested. Several derivatives showed low nanomolar activity both in the binding and in the functional assay. In a formalin-induced hyperalgesia model in mice, 6a and (4-benzylpiperidine-1-yl)-[5(6)-hydroxy-1H-benzimidazol-2-yl]-methanone (60a) were as active as besonprodil (2) after oral administration. A CoMSIA model was developed based on binding data of a series of indole- and benzimidazole-2-carboxamides.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm060420k</identifier><identifier>PMID: 17290978</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Analgesics - chemical synthesis ; Analgesics - chemistry ; Analgesics - pharmacology ; Animals ; Benzimidazoles - chemical synthesis ; Benzimidazoles - chemistry ; Benzimidazoles - pharmacology ; Biological and medical sciences ; Calcium - metabolism ; Cells, Cultured ; Glutamatergic system (aspartate and other excitatory aminoacids) ; In Vitro Techniques ; Indoles - chemical synthesis ; Indoles - chemistry ; Indoles - pharmacology ; Intracellular Space - metabolism ; Male ; Medical sciences ; Mice ; Models, Molecular ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Pain Measurement ; Patch-Clamp Techniques ; Pharmacology. Drug treatments ; Piperazines - chemical synthesis ; Piperazines - chemistry ; Piperazines - pharmacology ; Prosencephalon - cytology ; Prosencephalon - metabolism ; Quantitative Structure-Activity Relationship ; Radioligand Assay ; Rats ; Rats, Wistar ; Receptors, N-Methyl-D-Aspartate - antagonists & inhibitors</subject><ispartof>Journal of medicinal chemistry, 2007-03, Vol.50 (5), p.901-914</ispartof><rights>Copyright © 2007 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-50254dbfd6b21bdf4232cae11057565b3139dd88fded09431fec3bc69393d7693</citedby><cites>FETCH-LOGICAL-a381t-50254dbfd6b21bdf4232cae11057565b3139dd88fded09431fec3bc69393d7693</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/jm060420k$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm060420k$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18652241$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17290978$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Borza, István</creatorcontrib><creatorcontrib>Bozó, Éva</creatorcontrib><creatorcontrib>Barta-Szalai, Gizella</creatorcontrib><creatorcontrib>Kiss, Csilla</creatorcontrib><creatorcontrib>Tárkányi, Gábor</creatorcontrib><creatorcontrib>Demeter, Ádám</creatorcontrib><creatorcontrib>Gáti, Tamás</creatorcontrib><creatorcontrib>Háda, Viktor</creatorcontrib><creatorcontrib>Kolok, Sándor</creatorcontrib><creatorcontrib>Gere, Anikó</creatorcontrib><creatorcontrib>Fodor, László</creatorcontrib><creatorcontrib>Nagy, József</creatorcontrib><creatorcontrib>Galgóczy, Kornél</creatorcontrib><creatorcontrib>Magdó, Ildikó</creatorcontrib><creatorcontrib>Ágai, Béla</creatorcontrib><creatorcontrib>Fetter, József</creatorcontrib><creatorcontrib>Bertha, Ferenc</creatorcontrib><creatorcontrib>Keserü, György M</creatorcontrib><creatorcontrib>Horváth, Csilla</creatorcontrib><creatorcontrib>Farkas, Sándor</creatorcontrib><creatorcontrib>Greiner, István</creatorcontrib><creatorcontrib>Domány, György</creatorcontrib><title>Selective NR1/2B N-Methyl-d-aspartate Receptor Antagonists among Indole-2-carboxamides and Benzimidazole-2-carboxamides</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>(4-Benzylpiperidine-1-yl)-(6-hydroxy-1H-indole-2-yl)-methanone (6a) derived from (E)-1-(4-benzylpiperidin-1-yl)-3-(4-hydroxy-phenyl)-propenone (5) was identified as a potent NR2B subunit-selective antagonist of the NMDA receptor. To establish the structure−activity relationship (SAR) and to attempt the improvement of the ADME properties of the lead, a series of compounds were prepared and tested. Several derivatives showed low nanomolar activity both in the binding and in the functional assay. In a formalin-induced hyperalgesia model in mice, 6a and (4-benzylpiperidine-1-yl)-[5(6)-hydroxy-1H-benzimidazol-2-yl]-methanone (60a) were as active as besonprodil (2) after oral administration. A CoMSIA model was developed based on binding data of a series of indole- and benzimidazole-2-carboxamides.</description><subject>Analgesics - chemical synthesis</subject><subject>Analgesics - chemistry</subject><subject>Analgesics - pharmacology</subject><subject>Animals</subject><subject>Benzimidazoles - chemical synthesis</subject><subject>Benzimidazoles - chemistry</subject><subject>Benzimidazoles - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Calcium - metabolism</subject><subject>Cells, Cultured</subject><subject>Glutamatergic system (aspartate and other excitatory aminoacids)</subject><subject>In Vitro Techniques</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>Indoles - pharmacology</subject><subject>Intracellular Space - metabolism</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Models, Molecular</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Pain Measurement</subject><subject>Patch-Clamp Techniques</subject><subject>Pharmacology. Drug treatments</subject><subject>Piperazines - chemical synthesis</subject><subject>Piperazines - chemistry</subject><subject>Piperazines - pharmacology</subject><subject>Prosencephalon - cytology</subject><subject>Prosencephalon - metabolism</subject><subject>Quantitative Structure-Activity Relationship</subject><subject>Radioligand Assay</subject><subject>Rats</subject><subject>Rats, Wistar</subject><subject>Receptors, N-Methyl-D-Aspartate - antagonists & inhibitors</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1v1DAQgGELgehSOPAHUC4g9WBqj-N8HLsrCq3Cgtpy4WI59qRkm9hbOwttfz2udtU9wGlkzaOR9RLylrOPnAE_Xo2sYDmwm2dkxiUwmlcsf05mjAFQKEAckFcxrhhjgoN4SQ54CTWry2pG_lzigGbqf2O2vODHMM-W9CtOv-4HaqmOax0mPWF2gQbXkw_ZiZv0tXd9nGKmR--uszNn_YAUqNGh9Xd67C2mnbPZHN1Dn5764V_wmrzo9BDxzW4ekh-nn64WX2jz7fPZ4qShWlR8opKBzG3b2aIF3touBwFGI-dMlrKQreCitraqOouW1bngHRrRmqIWtbBlGofkw_buOvjbDcZJjX00OAzaod9EVaZEvJIywaMtNMHHGLBT69CPOtwrztRjZfVUOdl3u6ObdkS7l7usCbzfAR2NHrqgnenj3lWFBMh5cnTrUk-8e9rrcKOKUpRSXX2_VD8X0MyX541q9ne1iWrlN8Gldv_54F8mBZ_A</recordid><startdate>20070308</startdate><enddate>20070308</enddate><creator>Borza, István</creator><creator>Bozó, Éva</creator><creator>Barta-Szalai, Gizella</creator><creator>Kiss, Csilla</creator><creator>Tárkányi, Gábor</creator><creator>Demeter, Ádám</creator><creator>Gáti, Tamás</creator><creator>Háda, Viktor</creator><creator>Kolok, Sándor</creator><creator>Gere, Anikó</creator><creator>Fodor, László</creator><creator>Nagy, József</creator><creator>Galgóczy, Kornél</creator><creator>Magdó, Ildikó</creator><creator>Ágai, Béla</creator><creator>Fetter, József</creator><creator>Bertha, Ferenc</creator><creator>Keserü, György M</creator><creator>Horváth, Csilla</creator><creator>Farkas, Sándor</creator><creator>Greiner, István</creator><creator>Domány, György</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>20070308</creationdate><title>Selective NR1/2B N-Methyl-d-aspartate Receptor Antagonists among Indole-2-carboxamides and Benzimidazole-2-carboxamides</title><author>Borza, István ; Bozó, Éva ; Barta-Szalai, Gizella ; Kiss, Csilla ; Tárkányi, Gábor ; Demeter, Ádám ; Gáti, Tamás ; Háda, Viktor ; Kolok, Sándor ; Gere, Anikó ; Fodor, László ; Nagy, József ; Galgóczy, Kornél ; Magdó, Ildikó ; Ágai, Béla ; Fetter, József ; Bertha, Ferenc ; Keserü, György M ; Horváth, Csilla ; Farkas, Sándor ; Greiner, István ; Domány, György</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-50254dbfd6b21bdf4232cae11057565b3139dd88fded09431fec3bc69393d7693</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Analgesics - chemical synthesis</topic><topic>Analgesics - chemistry</topic><topic>Analgesics - pharmacology</topic><topic>Animals</topic><topic>Benzimidazoles - chemical synthesis</topic><topic>Benzimidazoles - chemistry</topic><topic>Benzimidazoles - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Calcium - metabolism</topic><topic>Cells, Cultured</topic><topic>Glutamatergic system (aspartate and other excitatory aminoacids)</topic><topic>In Vitro Techniques</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Indoles - pharmacology</topic><topic>Intracellular Space - metabolism</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Models, Molecular</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Pain Measurement</topic><topic>Patch-Clamp Techniques</topic><topic>Pharmacology. Drug treatments</topic><topic>Piperazines - chemical synthesis</topic><topic>Piperazines - chemistry</topic><topic>Piperazines - pharmacology</topic><topic>Prosencephalon - cytology</topic><topic>Prosencephalon - metabolism</topic><topic>Quantitative Structure-Activity Relationship</topic><topic>Radioligand Assay</topic><topic>Rats</topic><topic>Rats, Wistar</topic><topic>Receptors, N-Methyl-D-Aspartate - antagonists & inhibitors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Borza, István</creatorcontrib><creatorcontrib>Bozó, Éva</creatorcontrib><creatorcontrib>Barta-Szalai, Gizella</creatorcontrib><creatorcontrib>Kiss, Csilla</creatorcontrib><creatorcontrib>Tárkányi, Gábor</creatorcontrib><creatorcontrib>Demeter, Ádám</creatorcontrib><creatorcontrib>Gáti, Tamás</creatorcontrib><creatorcontrib>Háda, Viktor</creatorcontrib><creatorcontrib>Kolok, Sándor</creatorcontrib><creatorcontrib>Gere, Anikó</creatorcontrib><creatorcontrib>Fodor, László</creatorcontrib><creatorcontrib>Nagy, József</creatorcontrib><creatorcontrib>Galgóczy, Kornél</creatorcontrib><creatorcontrib>Magdó, Ildikó</creatorcontrib><creatorcontrib>Ágai, Béla</creatorcontrib><creatorcontrib>Fetter, József</creatorcontrib><creatorcontrib>Bertha, Ferenc</creatorcontrib><creatorcontrib>Keserü, György M</creatorcontrib><creatorcontrib>Horváth, Csilla</creatorcontrib><creatorcontrib>Farkas, Sándor</creatorcontrib><creatorcontrib>Greiner, István</creatorcontrib><creatorcontrib>Domány, György</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>Borza, István</au><au>Bozó, Éva</au><au>Barta-Szalai, Gizella</au><au>Kiss, Csilla</au><au>Tárkányi, Gábor</au><au>Demeter, Ádám</au><au>Gáti, Tamás</au><au>Háda, Viktor</au><au>Kolok, Sándor</au><au>Gere, Anikó</au><au>Fodor, László</au><au>Nagy, József</au><au>Galgóczy, Kornél</au><au>Magdó, Ildikó</au><au>Ágai, Béla</au><au>Fetter, József</au><au>Bertha, Ferenc</au><au>Keserü, György M</au><au>Horváth, Csilla</au><au>Farkas, Sándor</au><au>Greiner, István</au><au>Domány, György</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective NR1/2B N-Methyl-d-aspartate Receptor Antagonists among Indole-2-carboxamides and Benzimidazole-2-carboxamides</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2007-03-08</date><risdate>2007</risdate><volume>50</volume><issue>5</issue><spage>901</spage><epage>914</epage><pages>901-914</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>(4-Benzylpiperidine-1-yl)-(6-hydroxy-1H-indole-2-yl)-methanone (6a) derived from (E)-1-(4-benzylpiperidin-1-yl)-3-(4-hydroxy-phenyl)-propenone (5) was identified as a potent NR2B subunit-selective antagonist of the NMDA receptor. To establish the structure−activity relationship (SAR) and to attempt the improvement of the ADME properties of the lead, a series of compounds were prepared and tested. Several derivatives showed low nanomolar activity both in the binding and in the functional assay. In a formalin-induced hyperalgesia model in mice, 6a and (4-benzylpiperidine-1-yl)-[5(6)-hydroxy-1H-benzimidazol-2-yl]-methanone (60a) were as active as besonprodil (2) after oral administration. A CoMSIA model was developed based on binding data of a series of indole- and benzimidazole-2-carboxamides.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>17290978</pmid><doi>10.1021/jm060420k</doi><tpages>14</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 2007-03, Vol.50 (5), p.901-914 |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Analgesics - chemical synthesis Analgesics - chemistry Analgesics - pharmacology Animals Benzimidazoles - chemical synthesis Benzimidazoles - chemistry Benzimidazoles - pharmacology Biological and medical sciences Calcium - metabolism Cells, Cultured Glutamatergic system (aspartate and other excitatory aminoacids) In Vitro Techniques Indoles - chemical synthesis Indoles - chemistry Indoles - pharmacology Intracellular Space - metabolism Male Medical sciences Mice Models, Molecular Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Pain Measurement Patch-Clamp Techniques Pharmacology. Drug treatments Piperazines - chemical synthesis Piperazines - chemistry Piperazines - pharmacology Prosencephalon - cytology Prosencephalon - metabolism Quantitative Structure-Activity Relationship Radioligand Assay Rats Rats, Wistar Receptors, N-Methyl-D-Aspartate - antagonists & inhibitors |
| title | Selective NR1/2B N-Methyl-d-aspartate Receptor Antagonists among Indole-2-carboxamides and Benzimidazole-2-carboxamides |
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