Discovery and evaluation of selective N-type calcium channel blockers: 6-Unsubstituted-1,4-dihydropyridine-5-carboxylic acid derivatives
The structure–activity relationship study on 6-unsubstituted-1,4-dihydropyridine derivatives and 2,6-dihydro-1,4-dihydropyridine derivatives are reported as selective N-type calcium channel blockers over L-type calcium channel. A structure–activity relationship study of 6-unsubstituted-1,4-dihydropy...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2012-06, Vol.22 (11), p.3639-3642 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Yamamoto, Takashi Niwa, Seiji Tokumasu, Munetaka Onishi, Tomoyuki Ohno, Seiji Hagihara, Masako Koganei, Hajime Fujita, Shin-ichi Takeda, Tomoko Saitou, Yuki Iwayama, Satoshi Takahara, Akira Iwata, Seinosuke Shoji, Masataka |
| description | The structure–activity relationship study on 6-unsubstituted-1,4-dihydropyridine derivatives and 2,6-dihydro-1,4-dihydropyridine derivatives are reported as selective N-type calcium channel blockers over L-type calcium channel.
A structure–activity relationship study of 6-unsubstituted-1,4-dihydropyridine and 2,6-unsubstituted-1,4-dihydropyridine derivatives was conducted in an attempt to discover N-type calcium channel blockers that were highly selective over L-type calcium channel blockers. Among the tested compounds, (+)-4-(3,5-dichloro-4-methoxy-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-cinnamyl ester was found to be an effective and selective N-type calcium channel blocker with oral analgesic potential. |
| doi_str_mv | 10.1016/j.bmcl.2012.04.051 |
| format | Article |
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A structure–activity relationship study of 6-unsubstituted-1,4-dihydropyridine and 2,6-unsubstituted-1,4-dihydropyridine derivatives was conducted in an attempt to discover N-type calcium channel blockers that were highly selective over L-type calcium channel blockers. Among the tested compounds, (+)-4-(3,5-dichloro-4-methoxy-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-cinnamyl ester was found to be an effective and selective N-type calcium channel blocker with oral analgesic potential.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2012.04.051</identifier><identifier>PMID: 22560585</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>1,4-Dihydropyridine derivative ; Administration, Oral ; Analgesics ; Analgesics - chemical synthesis ; Analgesics - chemistry ; Analgesics - pharmacology ; Animals ; Biological and medical sciences ; calcium channel blockers ; Calcium Channel Blockers - chemical synthesis ; Calcium Channel Blockers - chemistry ; Calcium Channel Blockers - pharmacology ; calcium channels ; Calcium Channels, N-Type - chemistry ; Calcium Channels, N-Type - metabolism ; Carboxylic Acids - chemical synthesis ; Carboxylic Acids - chemistry ; Carboxylic Acids - pharmacology ; Dihydropyridines - chemistry ; Drug Evaluation, Preclinical ; Formaldehyde - toxicity ; Medical sciences ; N-Type calcium channel blocker ; Pain Measurement - drug effects ; Pharmacology. Drug treatments ; Rats ; Structure-Activity Relationship ; Structure–activity relationships</subject><ispartof>Bioorganic & medicinal chemistry letters, 2012-06, Vol.22 (11), p.3639-3642</ispartof><rights>2012 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c509t-1935201fa8c2dc3cbf38cb849402e191c5bba12fc900328ba0147fe4b6d5b2cd3</citedby><cites>FETCH-LOGICAL-c509t-1935201fa8c2dc3cbf38cb849402e191c5bba12fc900328ba0147fe4b6d5b2cd3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X1200501X$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25943926$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22560585$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yamamoto, Takashi</creatorcontrib><creatorcontrib>Niwa, Seiji</creatorcontrib><creatorcontrib>Tokumasu, Munetaka</creatorcontrib><creatorcontrib>Onishi, Tomoyuki</creatorcontrib><creatorcontrib>Ohno, Seiji</creatorcontrib><creatorcontrib>Hagihara, Masako</creatorcontrib><creatorcontrib>Koganei, Hajime</creatorcontrib><creatorcontrib>Fujita, Shin-ichi</creatorcontrib><creatorcontrib>Takeda, Tomoko</creatorcontrib><creatorcontrib>Saitou, Yuki</creatorcontrib><creatorcontrib>Iwayama, Satoshi</creatorcontrib><creatorcontrib>Takahara, Akira</creatorcontrib><creatorcontrib>Iwata, Seinosuke</creatorcontrib><creatorcontrib>Shoji, Masataka</creatorcontrib><title>Discovery and evaluation of selective N-type calcium channel blockers: 6-Unsubstituted-1,4-dihydropyridine-5-carboxylic acid derivatives</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>The structure–activity relationship study on 6-unsubstituted-1,4-dihydropyridine derivatives and 2,6-dihydro-1,4-dihydropyridine derivatives are reported as selective N-type calcium channel blockers over L-type calcium channel.
A structure–activity relationship study of 6-unsubstituted-1,4-dihydropyridine and 2,6-unsubstituted-1,4-dihydropyridine derivatives was conducted in an attempt to discover N-type calcium channel blockers that were highly selective over L-type calcium channel blockers. Among the tested compounds, (+)-4-(3,5-dichloro-4-methoxy-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-cinnamyl ester was found to be an effective and selective N-type calcium channel blocker with oral analgesic potential.</description><subject>1,4-Dihydropyridine derivative</subject><subject>Administration, Oral</subject><subject>Analgesics</subject><subject>Analgesics - chemical synthesis</subject><subject>Analgesics - chemistry</subject><subject>Analgesics - pharmacology</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>calcium channel blockers</subject><subject>Calcium Channel Blockers - chemical synthesis</subject><subject>Calcium Channel Blockers - chemistry</subject><subject>Calcium Channel Blockers - pharmacology</subject><subject>calcium channels</subject><subject>Calcium Channels, N-Type - chemistry</subject><subject>Calcium Channels, N-Type - metabolism</subject><subject>Carboxylic Acids - chemical synthesis</subject><subject>Carboxylic Acids - chemistry</subject><subject>Carboxylic Acids - pharmacology</subject><subject>Dihydropyridines - chemistry</subject><subject>Drug Evaluation, Preclinical</subject><subject>Formaldehyde - toxicity</subject><subject>Medical sciences</subject><subject>N-Type calcium channel blocker</subject><subject>Pain Measurement - drug effects</subject><subject>Pharmacology. Drug treatments</subject><subject>Rats</subject><subject>Structure-Activity Relationship</subject><subject>Structure–activity relationships</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkbuO1DAUhiMEYmcXXoAC3CBtgYPt2JlkRYOWq7SCAkais-zjE9ZDEg92MiJvwGPj0QzQIarTfOf2f0XxiLOSM14_35Z2gL4UjIuSyZIpfqdYcVlLWkmm7hYr1taMNq38clacp7RljEsm5f3iTAhVM9WoVfHzlU8Q9hgXYkZHcG_62Uw-jCR0JGGPMPk9kg90WnZIwPTg54HArRlH7IntA3zDmK5ITTdjmm2a_DRP6Ch_Jqnzt4uLYbdE7_yIVFEw0YYfS--BGPCOOIx-bw4b0oPiXmf6hA9P9aLYvHn9-fodvfn49v31yxsKirUT5W2l8sOdaUA4qMB2VQO2ka1kAnnLQVlruOigZawSjTX553WH0tZOWQGuuiguj3N3MXyfMU16yAlg35sRw5w0Z5VsuMjh_AfKq1Yc9mRUHFGIIaWInd5FP5i4ZOjA1XqrD7L0QZZmUmdZuenxaf5sB3R_Wn7bycDTE2BSjr6LZgSf_nKqlfmAOnNPjlxngjZfY2Y2n_ImlY1XrF6vM_HiSGCOdu8x6gQeR0DnY1asXfD_uvQXksO9PA</recordid><startdate>20120601</startdate><enddate>20120601</enddate><creator>Yamamoto, Takashi</creator><creator>Niwa, Seiji</creator><creator>Tokumasu, Munetaka</creator><creator>Onishi, Tomoyuki</creator><creator>Ohno, Seiji</creator><creator>Hagihara, Masako</creator><creator>Koganei, Hajime</creator><creator>Fujita, Shin-ichi</creator><creator>Takeda, Tomoko</creator><creator>Saitou, Yuki</creator><creator>Iwayama, Satoshi</creator><creator>Takahara, Akira</creator><creator>Iwata, Seinosuke</creator><creator>Shoji, Masataka</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</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><scope>7QO</scope><scope>7QP</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20120601</creationdate><title>Discovery and evaluation of selective N-type calcium channel blockers: 6-Unsubstituted-1,4-dihydropyridine-5-carboxylic acid derivatives</title><author>Yamamoto, Takashi ; Niwa, Seiji ; Tokumasu, Munetaka ; Onishi, Tomoyuki ; Ohno, Seiji ; Hagihara, Masako ; Koganei, Hajime ; Fujita, Shin-ichi ; Takeda, Tomoko ; Saitou, Yuki ; Iwayama, Satoshi ; Takahara, Akira ; Iwata, Seinosuke ; Shoji, Masataka</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c509t-1935201fa8c2dc3cbf38cb849402e191c5bba12fc900328ba0147fe4b6d5b2cd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>1,4-Dihydropyridine derivative</topic><topic>Administration, Oral</topic><topic>Analgesics</topic><topic>Analgesics - chemical synthesis</topic><topic>Analgesics - chemistry</topic><topic>Analgesics - pharmacology</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>calcium channel blockers</topic><topic>Calcium Channel Blockers - chemical synthesis</topic><topic>Calcium Channel Blockers - chemistry</topic><topic>Calcium Channel Blockers - pharmacology</topic><topic>calcium channels</topic><topic>Calcium Channels, N-Type - chemistry</topic><topic>Calcium Channels, N-Type - metabolism</topic><topic>Carboxylic Acids - chemical synthesis</topic><topic>Carboxylic Acids - chemistry</topic><topic>Carboxylic Acids - pharmacology</topic><topic>Dihydropyridines - chemistry</topic><topic>Drug Evaluation, Preclinical</topic><topic>Formaldehyde - toxicity</topic><topic>Medical sciences</topic><topic>N-Type calcium channel blocker</topic><topic>Pain Measurement - drug effects</topic><topic>Pharmacology. Drug treatments</topic><topic>Rats</topic><topic>Structure-Activity Relationship</topic><topic>Structure–activity relationships</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yamamoto, Takashi</creatorcontrib><creatorcontrib>Niwa, Seiji</creatorcontrib><creatorcontrib>Tokumasu, Munetaka</creatorcontrib><creatorcontrib>Onishi, Tomoyuki</creatorcontrib><creatorcontrib>Ohno, Seiji</creatorcontrib><creatorcontrib>Hagihara, Masako</creatorcontrib><creatorcontrib>Koganei, Hajime</creatorcontrib><creatorcontrib>Fujita, Shin-ichi</creatorcontrib><creatorcontrib>Takeda, Tomoko</creatorcontrib><creatorcontrib>Saitou, Yuki</creatorcontrib><creatorcontrib>Iwayama, Satoshi</creatorcontrib><creatorcontrib>Takahara, Akira</creatorcontrib><creatorcontrib>Iwata, Seinosuke</creatorcontrib><creatorcontrib>Shoji, Masataka</creatorcontrib><collection>AGRIS</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><collection>Biotechnology Research Abstracts</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yamamoto, Takashi</au><au>Niwa, Seiji</au><au>Tokumasu, Munetaka</au><au>Onishi, Tomoyuki</au><au>Ohno, Seiji</au><au>Hagihara, Masako</au><au>Koganei, Hajime</au><au>Fujita, Shin-ichi</au><au>Takeda, Tomoko</au><au>Saitou, Yuki</au><au>Iwayama, Satoshi</au><au>Takahara, Akira</au><au>Iwata, Seinosuke</au><au>Shoji, Masataka</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Discovery and evaluation of selective N-type calcium channel blockers: 6-Unsubstituted-1,4-dihydropyridine-5-carboxylic acid derivatives</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2012-06-01</date><risdate>2012</risdate><volume>22</volume><issue>11</issue><spage>3639</spage><epage>3642</epage><pages>3639-3642</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>The structure–activity relationship study on 6-unsubstituted-1,4-dihydropyridine derivatives and 2,6-dihydro-1,4-dihydropyridine derivatives are reported as selective N-type calcium channel blockers over L-type calcium channel.
A structure–activity relationship study of 6-unsubstituted-1,4-dihydropyridine and 2,6-unsubstituted-1,4-dihydropyridine derivatives was conducted in an attempt to discover N-type calcium channel blockers that were highly selective over L-type calcium channel blockers. Among the tested compounds, (+)-4-(3,5-dichloro-4-methoxy-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-cinnamyl ester was found to be an effective and selective N-type calcium channel blocker with oral analgesic potential.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>22560585</pmid><doi>10.1016/j.bmcl.2012.04.051</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2012-06, Vol.22 (11), p.3639-3642 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| subjects | 1,4-Dihydropyridine derivative Administration, Oral Analgesics Analgesics - chemical synthesis Analgesics - chemistry Analgesics - pharmacology Animals Biological and medical sciences calcium channel blockers Calcium Channel Blockers - chemical synthesis Calcium Channel Blockers - chemistry Calcium Channel Blockers - pharmacology calcium channels Calcium Channels, N-Type - chemistry Calcium Channels, N-Type - metabolism Carboxylic Acids - chemical synthesis Carboxylic Acids - chemistry Carboxylic Acids - pharmacology Dihydropyridines - chemistry Drug Evaluation, Preclinical Formaldehyde - toxicity Medical sciences N-Type calcium channel blocker Pain Measurement - drug effects Pharmacology. Drug treatments Rats Structure-Activity Relationship Structure–activity relationships |
| title | Discovery and evaluation of selective N-type calcium channel blockers: 6-Unsubstituted-1,4-dihydropyridine-5-carboxylic acid derivatives |
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