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Design of 1-substituted 2-arylmethyl-4,5-methylenedioxybenzene derivatives as antiseizure agents
A series of 1-substituted 2-[(4-aryl)-methyl]-4,5-methylenedioxybenzene derivatives were synthesized and sound-induced seizure test was used to evaluate their anticonvulsant activity. A series of 1-substituted 2-[(4-aryl)-methyl]-4,5-methylenedioxybenzene derivatives ( 13– 25), structurally related...
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| Published in: | Bioorganic & medicinal chemistry 2004-07, Vol.12 (13), p.3703-3709 |
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| Main Authors: | , , , , , , |
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| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c379t-fb1b115e9ff677488d53a8edab30d6f17e696126bb176cdd7b2ffeba630dfb153 |
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| cites | cdi_FETCH-LOGICAL-c379t-fb1b115e9ff677488d53a8edab30d6f17e696126bb176cdd7b2ffeba630dfb153 |
| container_end_page | 3709 |
| container_issue | 13 |
| container_start_page | 3703 |
| container_title | Bioorganic & medicinal chemistry |
| container_volume | 12 |
| creator | Micale, Nicola De Sarro, Giovambattista Ferreri, Guido Zappalá, Maria Grasso, Silvana Puia, Giulia De Micheli, Carlo |
| description | A series of 1-substituted 2-[(4-aryl)-methyl]-4,5-methylenedioxybenzene derivatives were synthesized and sound-induced seizure test was used to evaluate their anticonvulsant activity.
A series of 1-substituted 2-[(4-aryl)-methyl]-4,5-methylenedioxybenzene derivatives (
13–
25), structurally related to model compound
5 (2-[(4-aminophenyl)-(4-methylsemicarbazono)-methyl]-4,5-methylenedioxyphenylacetic acid methyl ester), were synthesized and tested as anticonvulsant agents in DBA/2 mice against sound-induced seizures. The new compounds possess anticonvulsant properties lower than those of prototype
5 but, in some instances, comparable to that of GYKI 52466, a well-known noncompetitive AMPA receptor antagonist. |
| doi_str_mv | 10.1016/j.bmc.2004.04.015 |
| format | article |
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A series of 1-substituted 2-[(4-aryl)-methyl]-4,5-methylenedioxybenzene derivatives (
13–
25), structurally related to model compound
5 (2-[(4-aminophenyl)-(4-methylsemicarbazono)-methyl]-4,5-methylenedioxyphenylacetic acid methyl ester), were synthesized and tested as anticonvulsant agents in DBA/2 mice against sound-induced seizures. The new compounds possess anticonvulsant properties lower than those of prototype
5 but, in some instances, comparable to that of GYKI 52466, a well-known noncompetitive AMPA receptor antagonist.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2004.04.015</identifier><identifier>PMID: 15186856</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Animals ; Anticonvulsants - chemical synthesis ; Anticonvulsants - chemistry ; Anticonvulsants - pharmacology ; Anticonvulsants - therapeutic use ; Anticonvulsants. Antiepileptics. Antiparkinson agents ; Benzene - chemical synthesis ; Benzene - chemistry ; Benzene - pharmacology ; Benzene - therapeutic use ; Biological and medical sciences ; Cells, Cultured ; Dioxoles - chemical synthesis ; Dioxoles - pharmacology ; Dioxoles - therapeutic use ; Drug Design ; Female ; Male ; Medical sciences ; Mice ; Mice, Inbred DBA ; Molecular Structure ; Neurons - drug effects ; Neuropharmacology ; Pharmacology. Drug treatments ; Seizures - drug therapy ; Seizures - physiopathology</subject><ispartof>Bioorganic & medicinal chemistry, 2004-07, Vol.12 (13), p.3703-3709</ispartof><rights>2004 Elsevier Ltd</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c379t-fb1b115e9ff677488d53a8edab30d6f17e696126bb176cdd7b2ffeba630dfb153</citedby><cites>FETCH-LOGICAL-c379t-fb1b115e9ff677488d53a8edab30d6f17e696126bb176cdd7b2ffeba630dfb153</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15859710$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15186856$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Micale, Nicola</creatorcontrib><creatorcontrib>De Sarro, Giovambattista</creatorcontrib><creatorcontrib>Ferreri, Guido</creatorcontrib><creatorcontrib>Zappalá, Maria</creatorcontrib><creatorcontrib>Grasso, Silvana</creatorcontrib><creatorcontrib>Puia, Giulia</creatorcontrib><creatorcontrib>De Micheli, Carlo</creatorcontrib><title>Design of 1-substituted 2-arylmethyl-4,5-methylenedioxybenzene derivatives as antiseizure agents</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A series of 1-substituted 2-[(4-aryl)-methyl]-4,5-methylenedioxybenzene derivatives were synthesized and sound-induced seizure test was used to evaluate their anticonvulsant activity.
A series of 1-substituted 2-[(4-aryl)-methyl]-4,5-methylenedioxybenzene derivatives (
13–
25), structurally related to model compound
5 (2-[(4-aminophenyl)-(4-methylsemicarbazono)-methyl]-4,5-methylenedioxyphenylacetic acid methyl ester), were synthesized and tested as anticonvulsant agents in DBA/2 mice against sound-induced seizures. The new compounds possess anticonvulsant properties lower than those of prototype
5 but, in some instances, comparable to that of GYKI 52466, a well-known noncompetitive AMPA receptor antagonist.</description><subject>Animals</subject><subject>Anticonvulsants - chemical synthesis</subject><subject>Anticonvulsants - chemistry</subject><subject>Anticonvulsants - pharmacology</subject><subject>Anticonvulsants - therapeutic use</subject><subject>Anticonvulsants. Antiepileptics. Antiparkinson agents</subject><subject>Benzene - chemical synthesis</subject><subject>Benzene - chemistry</subject><subject>Benzene - pharmacology</subject><subject>Benzene - therapeutic use</subject><subject>Biological and medical sciences</subject><subject>Cells, Cultured</subject><subject>Dioxoles - chemical synthesis</subject><subject>Dioxoles - pharmacology</subject><subject>Dioxoles - therapeutic use</subject><subject>Drug Design</subject><subject>Female</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Mice, Inbred DBA</subject><subject>Molecular Structure</subject><subject>Neurons - drug effects</subject><subject>Neuropharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Seizures - drug therapy</subject><subject>Seizures - physiopathology</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNp9kEuLFDEURoMoTjv6A9xIbXRl2tx6JFW4GsYnDLjRdczjZkxTjzE31djz603bDboSPsiFnPuRHMaeg9iCAPlmt7WT29ZCtNtjoHvANtDKljfNAA_ZRgyy56If5AV7QrQTQtTtAI_ZBXTQy76TG_b9HVK8naslVMBptZRjXjP6quYmHcYJ84_DyNvXHT-NOKOPy6-Dxfm-zJXHFPcmxz1SZUrmHAnj_ZqwMrc4Z3rKHgUzEj47n5fs24f3X68_8ZsvHz9fX91w16gh82DBAnQ4hCCVavved43p0RvbCC8DKJSDhFpaC0o675WtQ0BrZLkuu11zyV6deu_S8nNFynqK5HAczYzLSloVTVLJpoBwAl1aiBIGfZfiVD6rQeijVr3TRas-atXH_Cl_cS5f7YT-78bZYwFengFDzowhmdlF-ofru0GBKNzbE4dFxT5i0uQizq5ITeiy9kv8zzN-A2GplwI</recordid><startdate>20040701</startdate><enddate>20040701</enddate><creator>Micale, Nicola</creator><creator>De Sarro, Giovambattista</creator><creator>Ferreri, Guido</creator><creator>Zappalá, Maria</creator><creator>Grasso, Silvana</creator><creator>Puia, Giulia</creator><creator>De Micheli, Carlo</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>20040701</creationdate><title>Design of 1-substituted 2-arylmethyl-4,5-methylenedioxybenzene derivatives as antiseizure agents</title><author>Micale, Nicola ; De Sarro, Giovambattista ; Ferreri, Guido ; Zappalá, Maria ; Grasso, Silvana ; Puia, Giulia ; De Micheli, Carlo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c379t-fb1b115e9ff677488d53a8edab30d6f17e696126bb176cdd7b2ffeba630dfb153</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Animals</topic><topic>Anticonvulsants - chemical synthesis</topic><topic>Anticonvulsants - chemistry</topic><topic>Anticonvulsants - pharmacology</topic><topic>Anticonvulsants - therapeutic use</topic><topic>Anticonvulsants. Antiepileptics. Antiparkinson agents</topic><topic>Benzene - chemical synthesis</topic><topic>Benzene - chemistry</topic><topic>Benzene - pharmacology</topic><topic>Benzene - therapeutic use</topic><topic>Biological and medical sciences</topic><topic>Cells, Cultured</topic><topic>Dioxoles - chemical synthesis</topic><topic>Dioxoles - pharmacology</topic><topic>Dioxoles - therapeutic use</topic><topic>Drug Design</topic><topic>Female</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Mice, Inbred DBA</topic><topic>Molecular Structure</topic><topic>Neurons - drug effects</topic><topic>Neuropharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Seizures - drug therapy</topic><topic>Seizures - physiopathology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Micale, Nicola</creatorcontrib><creatorcontrib>De Sarro, Giovambattista</creatorcontrib><creatorcontrib>Ferreri, Guido</creatorcontrib><creatorcontrib>Zappalá, Maria</creatorcontrib><creatorcontrib>Grasso, Silvana</creatorcontrib><creatorcontrib>Puia, Giulia</creatorcontrib><creatorcontrib>De Micheli, Carlo</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>Micale, Nicola</au><au>De Sarro, Giovambattista</au><au>Ferreri, Guido</au><au>Zappalá, Maria</au><au>Grasso, Silvana</au><au>Puia, Giulia</au><au>De Micheli, Carlo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design of 1-substituted 2-arylmethyl-4,5-methylenedioxybenzene derivatives as antiseizure agents</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2004-07-01</date><risdate>2004</risdate><volume>12</volume><issue>13</issue><spage>3703</spage><epage>3709</epage><pages>3703-3709</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A series of 1-substituted 2-[(4-aryl)-methyl]-4,5-methylenedioxybenzene derivatives were synthesized and sound-induced seizure test was used to evaluate their anticonvulsant activity.
A series of 1-substituted 2-[(4-aryl)-methyl]-4,5-methylenedioxybenzene derivatives (
13–
25), structurally related to model compound
5 (2-[(4-aminophenyl)-(4-methylsemicarbazono)-methyl]-4,5-methylenedioxyphenylacetic acid methyl ester), were synthesized and tested as anticonvulsant agents in DBA/2 mice against sound-induced seizures. The new compounds possess anticonvulsant properties lower than those of prototype
5 but, in some instances, comparable to that of GYKI 52466, a well-known noncompetitive AMPA receptor antagonist.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>15186856</pmid><doi>10.1016/j.bmc.2004.04.015</doi><tpages>7</tpages></addata></record> |
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| source | ScienceDirect Journals |
| subjects | Animals Anticonvulsants - chemical synthesis Anticonvulsants - chemistry Anticonvulsants - pharmacology Anticonvulsants - therapeutic use Anticonvulsants. Antiepileptics. Antiparkinson agents Benzene - chemical synthesis Benzene - chemistry Benzene - pharmacology Benzene - therapeutic use Biological and medical sciences Cells, Cultured Dioxoles - chemical synthesis Dioxoles - pharmacology Dioxoles - therapeutic use Drug Design Female Male Medical sciences Mice Mice, Inbred DBA Molecular Structure Neurons - drug effects Neuropharmacology Pharmacology. Drug treatments Seizures - drug therapy Seizures - physiopathology |
| title | Design of 1-substituted 2-arylmethyl-4,5-methylenedioxybenzene derivatives as antiseizure agents |
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