Synthesis of Apicidin-Derived Quinolone Derivatives: Parasite-Selective Histone Deacetylase Inhibitors and Antiproliferative Agents
Apicidin's indole was efficiently converted into a series of N-substituted quinolone derivatives by indole N-alkylation followed by a two-step, one-pot, ozonolysis/aldol condensation protocol. The new quinolones exhibited good parasite selectivity and potency both at the level of their molecula...
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| Veröffentlicht in: | Journal of medicinal chemistry 2000-12, Vol.43 (25), p.4919-4922 |
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| container_issue | 25 |
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| container_title | Journal of medicinal chemistry |
| container_volume | 43 |
| creator | Meinke, Peter T Colletti, Steven L Doss, George Myers, Robert W Gurnett, Anne M Dulski, Paula M Darkin-Rattray, Sandra J Allocco, John J Galuska, Stefan Schmatz, Dennis M Wyvratt, Matthew J Fisher, Michael H |
| description | Apicidin's indole was efficiently converted into a series of N-substituted quinolone derivatives by indole N-alkylation followed by a two-step, one-pot, ozonolysis/aldol condensation protocol. The new quinolones exhibited good parasite selectivity and potency both at the level of their molecular target, histone deacetylase, and in their whole cell antiproliferative activity in vitro. |
| doi_str_mv | 10.1021/jm0001976 |
| format | Article |
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The new quinolones exhibited good parasite selectivity and potency both at the level of their molecular target, histone deacetylase, and in their whole cell antiproliferative activity in vitro.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm0001976</identifier><identifier>PMID: 11124001</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antimalarials - chemical synthesis ; Antimalarials - chemistry ; Antimalarials - pharmacology ; Antiparasitic agents ; Antiprotozoal Agents - chemical synthesis ; Antiprotozoal Agents - chemistry ; Antiprotozoal Agents - pharmacology ; Binding, Competitive ; Biological and medical sciences ; Cell Division - drug effects ; Cell Extracts ; Chickens ; Eimeria tenella - cytology ; Eimeria tenella - drug effects ; Eimeria tenella - metabolism ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - chemistry ; Enzyme Inhibitors - pharmacology ; HeLa Cells ; Histone Deacetylase Inhibitors ; Histone Deacetylases - metabolism ; Humans ; In Vitro Techniques ; Indoles - chemical synthesis ; Indoles - chemistry ; Indoles - pharmacology ; Liver - metabolism ; Medical sciences ; Peptides, Cyclic - chemistry ; Pharmacology. Drug treatments ; Plasmodium falciparum - drug effects ; Quinolones - chemical synthesis ; Quinolones - chemistry ; Quinolones - pharmacology ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 2000-12, Vol.43 (25), p.4919-4922</ispartof><rights>Copyright © 2000 American Chemical Society</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a377t-38fa295cbbf88a25b6361abfddeea0213d236acea2d6fa9b38dcf080b9b51d9b3</citedby><cites>FETCH-LOGICAL-a377t-38fa295cbbf88a25b6361abfddeea0213d236acea2d6fa9b38dcf080b9b51d9b3</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/jm0001976$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm0001976$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=843206$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11124001$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Meinke, Peter T</creatorcontrib><creatorcontrib>Colletti, Steven L</creatorcontrib><creatorcontrib>Doss, George</creatorcontrib><creatorcontrib>Myers, Robert W</creatorcontrib><creatorcontrib>Gurnett, Anne M</creatorcontrib><creatorcontrib>Dulski, Paula M</creatorcontrib><creatorcontrib>Darkin-Rattray, Sandra J</creatorcontrib><creatorcontrib>Allocco, John J</creatorcontrib><creatorcontrib>Galuska, Stefan</creatorcontrib><creatorcontrib>Schmatz, Dennis M</creatorcontrib><creatorcontrib>Wyvratt, Matthew J</creatorcontrib><creatorcontrib>Fisher, Michael H</creatorcontrib><title>Synthesis of Apicidin-Derived Quinolone Derivatives: Parasite-Selective Histone Deacetylase Inhibitors and Antiproliferative Agents</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Apicidin's indole was efficiently converted into a series of N-substituted quinolone derivatives by indole N-alkylation followed by a two-step, one-pot, ozonolysis/aldol condensation protocol. The new quinolones exhibited good parasite selectivity and potency both at the level of their molecular target, histone deacetylase, and in their whole cell antiproliferative activity in vitro.</description><subject>Animals</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antimalarials - chemical synthesis</subject><subject>Antimalarials - chemistry</subject><subject>Antimalarials - pharmacology</subject><subject>Antiparasitic agents</subject><subject>Antiprotozoal Agents - chemical synthesis</subject><subject>Antiprotozoal Agents - chemistry</subject><subject>Antiprotozoal Agents - pharmacology</subject><subject>Binding, Competitive</subject><subject>Biological and medical sciences</subject><subject>Cell Division - drug effects</subject><subject>Cell Extracts</subject><subject>Chickens</subject><subject>Eimeria tenella - cytology</subject><subject>Eimeria tenella - drug effects</subject><subject>Eimeria tenella - metabolism</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - chemistry</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>HeLa Cells</subject><subject>Histone Deacetylase Inhibitors</subject><subject>Histone Deacetylases - metabolism</subject><subject>Humans</subject><subject>In Vitro Techniques</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>Indoles - pharmacology</subject><subject>Liver - metabolism</subject><subject>Medical sciences</subject><subject>Peptides, Cyclic - chemistry</subject><subject>Pharmacology. Drug treatments</subject><subject>Plasmodium falciparum - drug effects</subject><subject>Quinolones - chemical synthesis</subject><subject>Quinolones - chemistry</subject><subject>Quinolones - 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>eNptkMmOEzEURS0EokNgwQ8gSwgkFgUeanDYRc3QjVoikIKt9coD7VBxBduFyI4VEr_Jl-B0RWHDyvL18X1PB6GHlDynhNEXmy0hhC6a-haa0YqRohSkvI1mhDBWsJrxM3Qvxk2GOGX8LjqjlLIyf5mhX-u9T9cmuogHi5c7p5x2vnhlgvtuNP4wOj_0gzf4JoGU0_jyz8_feAUBokumWJveqEOOL1xMEwrKpH0P0eBLf-06l4YQMXiNlz65XRh6Z024KcPLL8aneB_dsdBH8-B4ztGnN6_b84vi6v3by_PlVQG8aVLBhQW2qFTXWSGAVV3Nawqd1doYyCa4ZrzOw4Hp2sKi40IrSwTpFl1Fdb7P0dOpNy_xbTQxya2LyvQ9eDOMUTasFEJkY3P0bAJVGGIMxspdcFsIe0mJPEiXJ-mZfXQsHbut0f_Io-UMPD4CEBX0NoBXLp44UXJGDjXFRGWN5sfpFcJXWTe8qWS7Wkvafv7Yrt6tZZv5JxMPKsrNMAafzf1nvb9szqiB</recordid><startdate>20001214</startdate><enddate>20001214</enddate><creator>Meinke, Peter T</creator><creator>Colletti, Steven L</creator><creator>Doss, George</creator><creator>Myers, Robert W</creator><creator>Gurnett, Anne M</creator><creator>Dulski, Paula M</creator><creator>Darkin-Rattray, Sandra J</creator><creator>Allocco, John J</creator><creator>Galuska, Stefan</creator><creator>Schmatz, Dennis M</creator><creator>Wyvratt, Matthew J</creator><creator>Fisher, Michael H</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>20001214</creationdate><title>Synthesis of Apicidin-Derived Quinolone Derivatives: Parasite-Selective Histone Deacetylase Inhibitors and Antiproliferative Agents</title><author>Meinke, Peter T ; Colletti, Steven L ; Doss, George ; Myers, Robert W ; Gurnett, Anne M ; Dulski, Paula M ; Darkin-Rattray, Sandra J ; Allocco, John J ; Galuska, Stefan ; Schmatz, Dennis M ; Wyvratt, Matthew J ; Fisher, Michael H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a377t-38fa295cbbf88a25b6361abfddeea0213d236acea2d6fa9b38dcf080b9b51d9b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Animals</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antimalarials - chemical synthesis</topic><topic>Antimalarials - chemistry</topic><topic>Antimalarials - pharmacology</topic><topic>Antiparasitic agents</topic><topic>Antiprotozoal Agents - chemical synthesis</topic><topic>Antiprotozoal Agents - chemistry</topic><topic>Antiprotozoal Agents - pharmacology</topic><topic>Binding, Competitive</topic><topic>Biological and medical sciences</topic><topic>Cell Division - drug effects</topic><topic>Cell Extracts</topic><topic>Chickens</topic><topic>Eimeria tenella - cytology</topic><topic>Eimeria tenella - drug effects</topic><topic>Eimeria tenella - metabolism</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - chemistry</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>HeLa Cells</topic><topic>Histone Deacetylase Inhibitors</topic><topic>Histone Deacetylases - metabolism</topic><topic>Humans</topic><topic>In Vitro Techniques</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Indoles - pharmacology</topic><topic>Liver - metabolism</topic><topic>Medical sciences</topic><topic>Peptides, Cyclic - chemistry</topic><topic>Pharmacology. Drug treatments</topic><topic>Plasmodium falciparum - drug effects</topic><topic>Quinolones - chemical synthesis</topic><topic>Quinolones - chemistry</topic><topic>Quinolones - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Meinke, Peter T</creatorcontrib><creatorcontrib>Colletti, Steven L</creatorcontrib><creatorcontrib>Doss, George</creatorcontrib><creatorcontrib>Myers, Robert W</creatorcontrib><creatorcontrib>Gurnett, Anne M</creatorcontrib><creatorcontrib>Dulski, Paula M</creatorcontrib><creatorcontrib>Darkin-Rattray, Sandra J</creatorcontrib><creatorcontrib>Allocco, John J</creatorcontrib><creatorcontrib>Galuska, Stefan</creatorcontrib><creatorcontrib>Schmatz, Dennis M</creatorcontrib><creatorcontrib>Wyvratt, Matthew J</creatorcontrib><creatorcontrib>Fisher, Michael H</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>Meinke, Peter T</au><au>Colletti, Steven L</au><au>Doss, George</au><au>Myers, Robert W</au><au>Gurnett, Anne M</au><au>Dulski, Paula M</au><au>Darkin-Rattray, Sandra J</au><au>Allocco, John J</au><au>Galuska, Stefan</au><au>Schmatz, Dennis M</au><au>Wyvratt, Matthew J</au><au>Fisher, Michael H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Apicidin-Derived Quinolone Derivatives: Parasite-Selective Histone Deacetylase Inhibitors and Antiproliferative Agents</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2000-12-14</date><risdate>2000</risdate><volume>43</volume><issue>25</issue><spage>4919</spage><epage>4922</epage><pages>4919-4922</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>Apicidin's indole was efficiently converted into a series of N-substituted quinolone derivatives by indole N-alkylation followed by a two-step, one-pot, ozonolysis/aldol condensation protocol. The new quinolones exhibited good parasite selectivity and potency both at the level of their molecular target, histone deacetylase, and in their whole cell antiproliferative activity in vitro.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>11124001</pmid><doi>10.1021/jm0001976</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 2000-12, Vol.43 (25), p.4919-4922 |
| issn | 0022-2623 1520-4804 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antimalarials - chemical synthesis Antimalarials - chemistry Antimalarials - pharmacology Antiparasitic agents Antiprotozoal Agents - chemical synthesis Antiprotozoal Agents - chemistry Antiprotozoal Agents - pharmacology Binding, Competitive Biological and medical sciences Cell Division - drug effects Cell Extracts Chickens Eimeria tenella - cytology Eimeria tenella - drug effects Eimeria tenella - metabolism Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology HeLa Cells Histone Deacetylase Inhibitors Histone Deacetylases - metabolism Humans In Vitro Techniques Indoles - chemical synthesis Indoles - chemistry Indoles - pharmacology Liver - metabolism Medical sciences Peptides, Cyclic - chemistry Pharmacology. Drug treatments Plasmodium falciparum - drug effects Quinolones - chemical synthesis Quinolones - chemistry Quinolones - pharmacology Structure-Activity Relationship |
| title | Synthesis of Apicidin-Derived Quinolone Derivatives: Parasite-Selective Histone Deacetylase Inhibitors and Antiproliferative Agents |
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