Syntheses and Structure−Activity Relationships of 5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-quinoxaline Derivatives with Retinoic Acid Receptor α Agonistic Activity
In the course of our studies on retinoic acid receptor (RAR) agonists, we have designed and synthesized a series of quinoxaline derivatives. One of them, 4-[5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-quinoxalinyl)-1H-2-pyrrolyl]benzoic acid (3a), which possesses a 2,5-disubstituted pyrrole moiety,...
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| Veröffentlicht in: | Journal of medicinal chemistry 2000-02, Vol.43 (3), p.409-419 |
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| container_title | Journal of medicinal chemistry |
| container_volume | 43 |
| creator | Kikuchi, Kouichi Hibi, Shigeki Yoshimura, Hiroyuki Tokuhara, Naoki Tai, Kenji Hida, Takayuki Yamauchi, Toshihiko Nagai, Mitsuo |
| description | In the course of our studies on retinoic acid receptor (RAR) agonists, we have designed and synthesized a series of quinoxaline derivatives. One of them, 4-[5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-quinoxalinyl)-1H-2-pyrrolyl]benzoic acid (3a), which possesses a 2,5-disubstituted pyrrole moiety, showed selectivity for the RARα receptor and exerted highly potent cell-differentiating activity on HL-60 cells. |
| doi_str_mv | 10.1021/jm990063w |
| format | Article |
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One of them, 4-[5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-quinoxalinyl)-1H-2-pyrrolyl]benzoic acid (3a), which possesses a 2,5-disubstituted pyrrole moiety, showed selectivity for the RARα receptor and exerted highly potent cell-differentiating activity on HL-60 cells.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm990063w</identifier><identifier>PMID: 10669568</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Antineoplastic agents ; Benzoates - chemical synthesis ; Benzoates - chemistry ; Benzoates - metabolism ; Benzoates - pharmacology ; Binding, Competitive ; Biological and medical sciences ; Cell Differentiation - drug effects ; Cell Line ; General aspects ; Humans ; Medical sciences ; Pharmacology. Drug treatments ; Quinoxalines - chemical synthesis ; Quinoxalines - chemistry ; Quinoxalines - metabolism ; Quinoxalines - pharmacology ; Receptors, Retinoic Acid - agonists ; Receptors, Retinoic Acid - metabolism ; Retinoic Acid Receptor alpha ; Retinoids - chemical synthesis ; Retinoids - chemistry ; Retinoids - metabolism ; Retinoids - pharmacology ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 2000-02, Vol.43 (3), p.409-419</ispartof><rights>Copyright © 2000 American Chemical Society</rights><rights>2000 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a378t-d8dedd668c415e647b87930c74191411dba2305e458e4599ca9f15599807a5f63</citedby><cites>FETCH-LOGICAL-a378t-d8dedd668c415e647b87930c74191411dba2305e458e4599ca9f15599807a5f63</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/jm990063w$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm990063w$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1278391$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10669568$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kikuchi, Kouichi</creatorcontrib><creatorcontrib>Hibi, Shigeki</creatorcontrib><creatorcontrib>Yoshimura, Hiroyuki</creatorcontrib><creatorcontrib>Tokuhara, Naoki</creatorcontrib><creatorcontrib>Tai, Kenji</creatorcontrib><creatorcontrib>Hida, Takayuki</creatorcontrib><creatorcontrib>Yamauchi, Toshihiko</creatorcontrib><creatorcontrib>Nagai, Mitsuo</creatorcontrib><title>Syntheses and Structure−Activity Relationships of 5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-quinoxaline Derivatives with Retinoic Acid Receptor α Agonistic Activity</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>In the course of our studies on retinoic acid receptor (RAR) agonists, we have designed and synthesized a series of quinoxaline derivatives. One of them, 4-[5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-quinoxalinyl)-1H-2-pyrrolyl]benzoic acid (3a), which possesses a 2,5-disubstituted pyrrole moiety, showed selectivity for the RARα receptor and exerted highly potent cell-differentiating activity on HL-60 cells.</description><subject>Antineoplastic agents</subject><subject>Benzoates - chemical synthesis</subject><subject>Benzoates - chemistry</subject><subject>Benzoates - metabolism</subject><subject>Benzoates - pharmacology</subject><subject>Binding, Competitive</subject><subject>Biological and medical sciences</subject><subject>Cell Differentiation - drug effects</subject><subject>Cell Line</subject><subject>General aspects</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Quinoxalines - chemical synthesis</subject><subject>Quinoxalines - chemistry</subject><subject>Quinoxalines - metabolism</subject><subject>Quinoxalines - pharmacology</subject><subject>Receptors, Retinoic Acid - agonists</subject><subject>Receptors, Retinoic Acid - metabolism</subject><subject>Retinoic Acid Receptor alpha</subject><subject>Retinoids - chemical synthesis</subject><subject>Retinoids - chemistry</subject><subject>Retinoids - metabolism</subject><subject>Retinoids - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkcuO0zAUhiMEYsrAghdAWQASUgK-xLdlNVw1RSBa2Fqu41CXJO7YTmfyBqx5CPa8CA_Bk-CSamDBwrJ9_k__OTp_lt2H4CkECD7bdkIAQPHljWwGCQJlxUF1M5sBgFCJKMIn2Z0QtgAADBG-nZ1AQKkglM-y78uxjxsTTMhVX-fL6AcdB29-ff0219HubRzzD6ZV0bo-bOwu5K7JSUELVvByZaJXm7H2riQFKXgqxUOpM3EztiUqLwbbuyvV2t7kz423--SzT60ubdwk25hUq_O5tnX6abOLzuc_f-Tzz663If6RphnuZrca1QZz73ifZh9fvlidvS4X7169OZsvSoUZj2XNa1PXlHJdQWJoxdacCQw0q6CAFYT1WiEMiKkIT0cIrUQDSXpwwBRpKD7NHk--O-8uBhOi7GzQpm1Vb9wQJAMCQF4dwCcTqL0LwZtG7rztlB8lBPIQirwOJbEPjqbDujP1P-SUQgIeHgEVtGobr3ptw18OMY4FTFg5YWk35upaVv6LpAwzIlfvl5IzuPj09hzL88Q_mnilg9y6wfdpdf-Z7zdoVbG4</recordid><startdate>20000210</startdate><enddate>20000210</enddate><creator>Kikuchi, Kouichi</creator><creator>Hibi, Shigeki</creator><creator>Yoshimura, Hiroyuki</creator><creator>Tokuhara, Naoki</creator><creator>Tai, Kenji</creator><creator>Hida, Takayuki</creator><creator>Yamauchi, Toshihiko</creator><creator>Nagai, 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><scope>7X8</scope></search><sort><creationdate>20000210</creationdate><title>Syntheses and Structure−Activity Relationships of 5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-quinoxaline Derivatives with Retinoic Acid Receptor α Agonistic Activity</title><author>Kikuchi, Kouichi ; Hibi, Shigeki ; Yoshimura, Hiroyuki ; Tokuhara, Naoki ; Tai, Kenji ; Hida, Takayuki ; Yamauchi, Toshihiko ; Nagai, Mitsuo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a378t-d8dedd668c415e647b87930c74191411dba2305e458e4599ca9f15599807a5f63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Antineoplastic agents</topic><topic>Benzoates - chemical synthesis</topic><topic>Benzoates - chemistry</topic><topic>Benzoates - metabolism</topic><topic>Benzoates - pharmacology</topic><topic>Binding, Competitive</topic><topic>Biological and medical sciences</topic><topic>Cell Differentiation - drug effects</topic><topic>Cell Line</topic><topic>General aspects</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Quinoxalines - chemical synthesis</topic><topic>Quinoxalines - chemistry</topic><topic>Quinoxalines - metabolism</topic><topic>Quinoxalines - pharmacology</topic><topic>Receptors, Retinoic Acid - agonists</topic><topic>Receptors, Retinoic Acid - metabolism</topic><topic>Retinoic Acid Receptor alpha</topic><topic>Retinoids - chemical synthesis</topic><topic>Retinoids - chemistry</topic><topic>Retinoids - metabolism</topic><topic>Retinoids - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kikuchi, Kouichi</creatorcontrib><creatorcontrib>Hibi, Shigeki</creatorcontrib><creatorcontrib>Yoshimura, Hiroyuki</creatorcontrib><creatorcontrib>Tokuhara, Naoki</creatorcontrib><creatorcontrib>Tai, Kenji</creatorcontrib><creatorcontrib>Hida, Takayuki</creatorcontrib><creatorcontrib>Yamauchi, Toshihiko</creatorcontrib><creatorcontrib>Nagai, 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><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kikuchi, Kouichi</au><au>Hibi, Shigeki</au><au>Yoshimura, Hiroyuki</au><au>Tokuhara, Naoki</au><au>Tai, Kenji</au><au>Hida, Takayuki</au><au>Yamauchi, Toshihiko</au><au>Nagai, Mitsuo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Syntheses and Structure−Activity Relationships of 5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-quinoxaline Derivatives with Retinoic Acid Receptor α Agonistic Activity</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2000-02-10</date><risdate>2000</risdate><volume>43</volume><issue>3</issue><spage>409</spage><epage>419</epage><pages>409-419</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>In the course of our studies on retinoic acid receptor (RAR) agonists, we have designed and synthesized a series of quinoxaline derivatives. One of them, 4-[5-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-quinoxalinyl)-1H-2-pyrrolyl]benzoic acid (3a), which possesses a 2,5-disubstituted pyrrole moiety, showed selectivity for the RARα receptor and exerted highly potent cell-differentiating activity on HL-60 cells.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>10669568</pmid><doi>10.1021/jm990063w</doi><tpages>11</tpages></addata></record> |
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| subjects | Antineoplastic agents Benzoates - chemical synthesis Benzoates - chemistry Benzoates - metabolism Benzoates - pharmacology Binding, Competitive Biological and medical sciences Cell Differentiation - drug effects Cell Line General aspects Humans Medical sciences Pharmacology. Drug treatments Quinoxalines - chemical synthesis Quinoxalines - chemistry Quinoxalines - metabolism Quinoxalines - pharmacology Receptors, Retinoic Acid - agonists Receptors, Retinoic Acid - metabolism Retinoic Acid Receptor alpha Retinoids - chemical synthesis Retinoids - chemistry Retinoids - metabolism Retinoids - pharmacology Structure-Activity Relationship |
| title | Syntheses and Structure−Activity Relationships of 5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-quinoxaline Derivatives with Retinoic Acid Receptor α Agonistic Activity |
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