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Substituted (.omega.-aminoalkoxy)stilbene derivatives as a new class of anticonvulsants
A series of substituted (omega- aminoalkoxy )stilbene derivatives has been synthesized and screened for anticonvulsant activity. The effect of structural modification of these molecules on the activities has been systematically examined. Potent anticonvulsant activity was displayed by 2-[4-(4-methyl...
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| Published in: | Journal of medicinal chemistry 1984-05, Vol.27 (5), p.645-649 |
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| Main Authors: | , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-a383t-69e641c460387e69ad7e0234b1eb7fa581959684ebdaa15fbcada32d1f9dff803 |
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| container_end_page | 649 |
| container_issue | 5 |
| container_start_page | 645 |
| container_title | Journal of medicinal chemistry |
| container_volume | 27 |
| creator | Kikumoto, Ryoji Tobe, Akihiro Fukami, Harukazu Ninomiya, Kunihiro Egawa, Mitsuo |
| description | A series of substituted (omega- aminoalkoxy )stilbene derivatives has been synthesized and screened for anticonvulsant activity. The effect of structural modification of these molecules on the activities has been systematically examined. Potent anticonvulsant activity was displayed by 2-[4-(4-methyl-1 piperazinyl)butoxy]stilbene (20) and some 2-[4-(3-alkoxy-1-piperidino)butoxy]stilbene derivatives (21, 37, 38, and 40), as determined by maximal electroshock seizure (MES) and pentylenetetrazol-induced convulsion tests in mice. Compound 21 exhibited more potent anti-MES activity than diphenylhydantoin and carbamazepine in further pharmacological tests in rats, and its therapeutic index was superior to those of two antiepileptic drugs. |
| doi_str_mv | 10.1021/jm00371a015 |
| format | article |
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The effect of structural modification of these molecules on the activities has been systematically examined. Potent anticonvulsant activity was displayed by 2-[4-(4-methyl-1 piperazinyl)butoxy]stilbene (20) and some 2-[4-(3-alkoxy-1-piperidino)butoxy]stilbene derivatives (21, 37, 38, and 40), as determined by maximal electroshock seizure (MES) and pentylenetetrazol-induced convulsion tests in mice. Compound 21 exhibited more potent anti-MES activity than diphenylhydantoin and carbamazepine in further pharmacological tests in rats, and its therapeutic index was superior to those of two antiepileptic drugs.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00371a015</identifier><identifier>PMID: 6716402</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Anticonvulsants - chemical synthesis ; Biological and medical sciences ; Biological Assay ; Drug Evaluation, Preclinical ; Electroshock ; General pharmacology ; Indicators and Reagents ; Male ; Medical sciences ; Mice ; Mice, Inbred Strains ; Pentylenetetrazole - toxicity ; Pharmacology. Drug treatments ; Physicochemical properties. Structure-activity relationships ; Rats ; Rats, Inbred Strains ; Seizures - drug therapy ; Stilbenes - chemical synthesis ; Stilbenes - toxicity ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 1984-05, Vol.27 (5), p.645-649</ispartof><rights>1984 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a383t-69e641c460387e69ad7e0234b1eb7fa581959684ebdaa15fbcada32d1f9dff803</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm00371a015$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00371a015$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,27064,27924,27925,56766,56816</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=9610304$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/6716402$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kikumoto, Ryoji</creatorcontrib><creatorcontrib>Tobe, Akihiro</creatorcontrib><creatorcontrib>Fukami, Harukazu</creatorcontrib><creatorcontrib>Ninomiya, Kunihiro</creatorcontrib><creatorcontrib>Egawa, Mitsuo</creatorcontrib><title>Substituted (.omega.-aminoalkoxy)stilbene derivatives as a new class of anticonvulsants</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A series of substituted (omega- aminoalkoxy )stilbene derivatives has been synthesized and screened for anticonvulsant activity. The effect of structural modification of these molecules on the activities has been systematically examined. Potent anticonvulsant activity was displayed by 2-[4-(4-methyl-1 piperazinyl)butoxy]stilbene (20) and some 2-[4-(3-alkoxy-1-piperidino)butoxy]stilbene derivatives (21, 37, 38, and 40), as determined by maximal electroshock seizure (MES) and pentylenetetrazol-induced convulsion tests in mice. Compound 21 exhibited more potent anti-MES activity than diphenylhydantoin and carbamazepine in further pharmacological tests in rats, and its therapeutic index was superior to those of two antiepileptic drugs.</description><subject>Animals</subject><subject>Anticonvulsants - chemical synthesis</subject><subject>Biological and medical sciences</subject><subject>Biological Assay</subject><subject>Drug Evaluation, Preclinical</subject><subject>Electroshock</subject><subject>General pharmacology</subject><subject>Indicators and Reagents</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Mice, Inbred Strains</subject><subject>Pentylenetetrazole - toxicity</subject><subject>Pharmacology. Drug treatments</subject><subject>Physicochemical properties. Structure-activity relationships</subject><subject>Rats</subject><subject>Rats, Inbred Strains</subject><subject>Seizures - drug therapy</subject><subject>Stilbenes - chemical synthesis</subject><subject>Stilbenes - toxicity</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1984</creationdate><recordtype>article</recordtype><recordid>eNpt0F1LwzAUBuAgypzTK6-FXggq0nmStGl7KcMv2FTYRPGmnLaJdOvHSNq5_XsjHcMLIXAC78Ph8BJySmFIgdGbeQnAA4pA_T3Spz4D1wvB2yd9AMZcJhg_JEfGzME6yniP9ERAhQesT96nbWKavGkbmTmXw7qUXzh0scyrGotFvd5c2bRIZCWdTOp8hU2-ksZB-5xKfjtpgcY4tXKwavK0rlZtYezXHJMDhYWRJ9s5IG_3d7PRozt-eXga3Y5d5CFvXBFJ4dHUE8DDQIoIs0AC415CZRIo9EMa-ZEIPZlkiNRXSYoZcpZRFWVKhcAH5Lrbm-raGC1VvNR5iXoTU4h_24n_tGP1WaeXbVLKbGe3ddj8fJujSbFQGqs0NzsWCQocPMvcjuWmketdjHphN_HAj2ev09gP-eTzg03iZ-svOo-pied1qytbyb8H_gA4KYjq</recordid><startdate>198405</startdate><enddate>198405</enddate><creator>Kikumoto, Ryoji</creator><creator>Tobe, Akihiro</creator><creator>Fukami, Harukazu</creator><creator>Ninomiya, Kunihiro</creator><creator>Egawa, Mitsuo</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></search><sort><creationdate>198405</creationdate><title>Substituted (.omega.-aminoalkoxy)stilbene derivatives as a new class of anticonvulsants</title><author>Kikumoto, Ryoji ; Tobe, Akihiro ; Fukami, Harukazu ; Ninomiya, Kunihiro ; Egawa, Mitsuo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a383t-69e641c460387e69ad7e0234b1eb7fa581959684ebdaa15fbcada32d1f9dff803</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1984</creationdate><topic>Animals</topic><topic>Anticonvulsants - chemical synthesis</topic><topic>Biological and medical sciences</topic><topic>Biological Assay</topic><topic>Drug Evaluation, Preclinical</topic><topic>Electroshock</topic><topic>General pharmacology</topic><topic>Indicators and Reagents</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Mice, Inbred Strains</topic><topic>Pentylenetetrazole - toxicity</topic><topic>Pharmacology. Drug treatments</topic><topic>Physicochemical properties. Structure-activity relationships</topic><topic>Rats</topic><topic>Rats, Inbred Strains</topic><topic>Seizures - drug therapy</topic><topic>Stilbenes - chemical synthesis</topic><topic>Stilbenes - toxicity</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kikumoto, Ryoji</creatorcontrib><creatorcontrib>Tobe, Akihiro</creatorcontrib><creatorcontrib>Fukami, Harukazu</creatorcontrib><creatorcontrib>Ninomiya, Kunihiro</creatorcontrib><creatorcontrib>Egawa, Mitsuo</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><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kikumoto, Ryoji</au><au>Tobe, Akihiro</au><au>Fukami, Harukazu</au><au>Ninomiya, Kunihiro</au><au>Egawa, Mitsuo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Substituted (.omega.-aminoalkoxy)stilbene derivatives as a new class of anticonvulsants</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1984-05</date><risdate>1984</risdate><volume>27</volume><issue>5</issue><spage>645</spage><epage>649</epage><pages>645-649</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>A series of substituted (omega- aminoalkoxy )stilbene derivatives has been synthesized and screened for anticonvulsant activity. The effect of structural modification of these molecules on the activities has been systematically examined. Potent anticonvulsant activity was displayed by 2-[4-(4-methyl-1 piperazinyl)butoxy]stilbene (20) and some 2-[4-(3-alkoxy-1-piperidino)butoxy]stilbene derivatives (21, 37, 38, and 40), as determined by maximal electroshock seizure (MES) and pentylenetetrazol-induced convulsion tests in mice. Compound 21 exhibited more potent anti-MES activity than diphenylhydantoin and carbamazepine in further pharmacological tests in rats, and its therapeutic index was superior to those of two antiepileptic drugs.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>6716402</pmid><doi>10.1021/jm00371a015</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1984-05, Vol.27 (5), p.645-649 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_crossref_primary_10_1021_jm00371a015 |
| source | ACS CRKN Legacy Archives |
| subjects | Animals Anticonvulsants - chemical synthesis Biological and medical sciences Biological Assay Drug Evaluation, Preclinical Electroshock General pharmacology Indicators and Reagents Male Medical sciences Mice Mice, Inbred Strains Pentylenetetrazole - toxicity Pharmacology. Drug treatments Physicochemical properties. Structure-activity relationships Rats Rats, Inbred Strains Seizures - drug therapy Stilbenes - chemical synthesis Stilbenes - toxicity Structure-Activity Relationship |
| title | Substituted (.omega.-aminoalkoxy)stilbene derivatives as a new class of anticonvulsants |
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