4-Amino-5-vinyl-3(2 H)-pyridazinones and analogues as potent antinociceptive agents: Synthesis, SARs, and preliminary studies on the mechanism of action
A series of 4-amino-5-vinyl-3(2 H)-pyridazinones and analogues were synthesized and their antinociceptive effect was evaluated in the mouse abdominal constriction model. Several of the novel compounds showed ED 50 values in the range 6–20 mg/kg/sc and demonstrated to be able to completely protect al...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2007-08, Vol.15 (16), p.5563-5575 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Vergelli, Claudia Giovannoni, Maria Paola Pieretti, Stefano Giannuario, Amalia Di Piaz, Vittorio Dal Biagini, Pierfrancesco Biancalani, Claudio Graziano, Alessia Cesari, Nicoletta |
| description | A series of 4-amino-5-vinyl-3(2
H)-pyridazinones and analogues were synthesized and their antinociceptive effect was evaluated in the mouse abdominal constriction model. Several of the novel compounds showed ED
50 values in the range 6–20
mg/kg/sc and demonstrated to be able to completely protect all the treated animals from the effect of the noxious stimulus at 30
mg/kg/sc. SAR studies confirmed the essential role played by an amino or substituted amino function at position 4 and by a vinyl group at position 5 of the diazine system. |
| doi_str_mv | 10.1016/j.bmc.2007.05.035 |
| format | Article |
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mg/kg/sc and demonstrated to be able to completely protect all the treated animals from the effect of the noxious stimulus at 30
mg/kg/sc. SAR studies confirmed the essential role played by an amino or substituted amino function at position 4 and by a vinyl group at position 5 of the diazine system.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2007.05.035</identifier><identifier>PMID: 17548197</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Amination ; Analgesics ; Animals ; Antinociception ; Behavior, Animal - drug effects ; Biological and medical sciences ; Male ; Medical sciences ; Mice ; Molecular Structure ; Neuropharmacology ; Nociceptors - metabolism ; Pain ; Pharmacology. Drug treatments ; Pyridines - chemical synthesis ; Pyridines - chemistry ; Pyridines - pharmacology ; SARs ; Structure-Activity Relationship ; Vinylpyridazinones</subject><ispartof>Bioorganic & medicinal chemistry, 2007-08, Vol.15 (16), p.5563-5575</ispartof><rights>2007 Elsevier Ltd</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c381t-d271addfff7ea2121205ba8b3c049d5456737b4b4c928e8ca9bbad14e04eccee3</citedby><cites>FETCH-LOGICAL-c381t-d271addfff7ea2121205ba8b3c049d5456737b4b4c928e8ca9bbad14e04eccee3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0968089607004506$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18886845$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17548197$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Vergelli, Claudia</creatorcontrib><creatorcontrib>Giovannoni, Maria Paola</creatorcontrib><creatorcontrib>Pieretti, Stefano</creatorcontrib><creatorcontrib>Giannuario, Amalia Di</creatorcontrib><creatorcontrib>Piaz, Vittorio Dal</creatorcontrib><creatorcontrib>Biagini, Pierfrancesco</creatorcontrib><creatorcontrib>Biancalani, Claudio</creatorcontrib><creatorcontrib>Graziano, Alessia</creatorcontrib><creatorcontrib>Cesari, Nicoletta</creatorcontrib><title>4-Amino-5-vinyl-3(2 H)-pyridazinones and analogues as potent antinociceptive agents: Synthesis, SARs, and preliminary studies on the mechanism of action</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A series of 4-amino-5-vinyl-3(2
H)-pyridazinones and analogues were synthesized and their antinociceptive effect was evaluated in the mouse abdominal constriction model. Several of the novel compounds showed ED
50 values in the range 6–20
mg/kg/sc and demonstrated to be able to completely protect all the treated animals from the effect of the noxious stimulus at 30
mg/kg/sc. SAR studies confirmed the essential role played by an amino or substituted amino function at position 4 and by a vinyl group at position 5 of the diazine system.</description><subject>Amination</subject><subject>Analgesics</subject><subject>Animals</subject><subject>Antinociception</subject><subject>Behavior, Animal - drug effects</subject><subject>Biological and medical sciences</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Neuropharmacology</subject><subject>Nociceptors - metabolism</subject><subject>Pain</subject><subject>Pharmacology. Drug treatments</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - chemistry</subject><subject>Pyridines - pharmacology</subject><subject>SARs</subject><subject>Structure-Activity Relationship</subject><subject>Vinylpyridazinones</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kdGO1CAUhonRuOPqA3hjuNFoIhVaSqleTTbqmmxi4uo1oXC6y6SFCswk45P4uNLMJHtnCBAO3_nhnB-hl4xWjDLxYVcNs6lqSruKthVt2kdow7jgpGl69hhtaC8kobIXF-hZSjtKac179hRdsK7lkvXdBv3lZDs7H0hLDs4fJ9K8rfH1O7Ico7P6T7nxkLD2tkw9hbv9ekp4CRl8LrFcCOMMLNkdAOu7Ek0f8e3R53tILr3Ht9sfZV0FlgiTK2_peMQp760rUsHjAuIZzL32Ls04jFib7IJ_jp6Mekrw4rxfol9fPv-8uiY3379-u9reENNIlomtO6atHcexA12zMmg7aDk0hvLetrwVXdMNfOCmryVIo_th0JZxoByMAWgu0ZuT7hLD71JdVrNLBqZJewj7pDoqBBV1U0B2Ak0MKUUY1RLdXIpRjKrVDrVTxQ612qFoq4odJefVWXw_zGAfMs79L8DrM6CT0dMYtTcuPXBSSiH5KvTpxEFpxcFBVMk48Aasi2CyssH95xv_AKycqhk</recordid><startdate>20070815</startdate><enddate>20070815</enddate><creator>Vergelli, Claudia</creator><creator>Giovannoni, Maria Paola</creator><creator>Pieretti, Stefano</creator><creator>Giannuario, Amalia Di</creator><creator>Piaz, Vittorio Dal</creator><creator>Biagini, Pierfrancesco</creator><creator>Biancalani, Claudio</creator><creator>Graziano, Alessia</creator><creator>Cesari, Nicoletta</creator><general>Elsevier Ltd</general><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>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20070815</creationdate><title>4-Amino-5-vinyl-3(2 H)-pyridazinones and analogues as potent antinociceptive agents: Synthesis, SARs, and preliminary studies on the mechanism of action</title><author>Vergelli, Claudia ; Giovannoni, Maria Paola ; Pieretti, Stefano ; Giannuario, Amalia Di ; Piaz, Vittorio Dal ; Biagini, Pierfrancesco ; Biancalani, Claudio ; Graziano, Alessia ; Cesari, Nicoletta</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c381t-d271addfff7ea2121205ba8b3c049d5456737b4b4c928e8ca9bbad14e04eccee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Amination</topic><topic>Analgesics</topic><topic>Animals</topic><topic>Antinociception</topic><topic>Behavior, Animal - drug effects</topic><topic>Biological and medical sciences</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>Neuropharmacology</topic><topic>Nociceptors - metabolism</topic><topic>Pain</topic><topic>Pharmacology. Drug treatments</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - chemistry</topic><topic>Pyridines - pharmacology</topic><topic>SARs</topic><topic>Structure-Activity Relationship</topic><topic>Vinylpyridazinones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Vergelli, Claudia</creatorcontrib><creatorcontrib>Giovannoni, Maria Paola</creatorcontrib><creatorcontrib>Pieretti, Stefano</creatorcontrib><creatorcontrib>Giannuario, Amalia Di</creatorcontrib><creatorcontrib>Piaz, Vittorio Dal</creatorcontrib><creatorcontrib>Biagini, Pierfrancesco</creatorcontrib><creatorcontrib>Biancalani, Claudio</creatorcontrib><creatorcontrib>Graziano, Alessia</creatorcontrib><creatorcontrib>Cesari, Nicoletta</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>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Vergelli, Claudia</au><au>Giovannoni, Maria Paola</au><au>Pieretti, Stefano</au><au>Giannuario, Amalia Di</au><au>Piaz, Vittorio Dal</au><au>Biagini, Pierfrancesco</au><au>Biancalani, Claudio</au><au>Graziano, Alessia</au><au>Cesari, Nicoletta</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>4-Amino-5-vinyl-3(2 H)-pyridazinones and analogues as potent antinociceptive agents: Synthesis, SARs, and preliminary studies on the mechanism of action</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2007-08-15</date><risdate>2007</risdate><volume>15</volume><issue>16</issue><spage>5563</spage><epage>5575</epage><pages>5563-5575</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A series of 4-amino-5-vinyl-3(2
H)-pyridazinones and analogues were synthesized and their antinociceptive effect was evaluated in the mouse abdominal constriction model. Several of the novel compounds showed ED
50 values in the range 6–20
mg/kg/sc and demonstrated to be able to completely protect all the treated animals from the effect of the noxious stimulus at 30
mg/kg/sc. SAR studies confirmed the essential role played by an amino or substituted amino function at position 4 and by a vinyl group at position 5 of the diazine system.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>17548197</pmid><doi>10.1016/j.bmc.2007.05.035</doi><tpages>13</tpages></addata></record> |
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| subjects | Amination Analgesics Animals Antinociception Behavior, Animal - drug effects Biological and medical sciences Male Medical sciences Mice Molecular Structure Neuropharmacology Nociceptors - metabolism Pain Pharmacology. Drug treatments Pyridines - chemical synthesis Pyridines - chemistry Pyridines - pharmacology SARs Structure-Activity Relationship Vinylpyridazinones |
| title | 4-Amino-5-vinyl-3(2 H)-pyridazinones and analogues as potent antinociceptive agents: Synthesis, SARs, and preliminary studies on the mechanism of action |
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