Loading…
Studies on quinones. Part 41: Synthesis and cytotoxicity of isoquinoline-containing polycyclic quinones
The regioselective synthesis of fused isoquinolinequinones (i.e., 6, 8, 13, and 15) through highly regiocontrolled cycloaddition reactions from methyl 1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate 3 and 1,3-dienes is reported. The 2-aza- and 1,6-diaza-anthraquinone derivatives display...
Saved in:
| Published in: | Bioorganic & medicinal chemistry 2006-07, Vol.14 (14), p.5003-5011 |
|---|---|
| Main Authors: | , , , , , , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| Citations: | Items that cite this one |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| cited_by | cdi_FETCH-LOGICAL-c412t-c113bb35e44dc7e4abddc217e1fd545a6d090ed12bc00c178d750f5478ac68e43 |
|---|---|
| cites | |
| container_end_page | 5011 |
| container_issue | 14 |
| container_start_page | 5003 |
| container_title | Bioorganic & medicinal chemistry |
| container_volume | 14 |
| creator | Valderrama, Jaime A. González, M. Florencia Pessoa-Mahana, David Tapia, Ricardo A. Fillion, Houda Pautet, Felix Rodriguez, Jaime A. Theoduloz, Cristina Schmeda-Hirschmann, Guillermo |
| description | The regioselective synthesis of fused isoquinolinequinones (i.e.,
6,
8,
13, and
15) through highly regiocontrolled cycloaddition reactions from methyl 1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate
3 and 1,3-dienes is reported. The 2-aza- and 1,6-diaza-anthraquinone derivatives displayed significant in vitro activity on normal fibroblast and four tumor cell lines.
In the search for new potentially anticancer drugs, isoquinolinequinone-containing polycyclic compounds have been designed and synthesized through highly regiocontrolled cycloaddition reactions of methyl 1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate with polarized 1,3-dienes and a thiazole-
o-quinodimethane. The new
N-heterocyclic quinones were tested on normal human fibroblasts and four distinct human cancer cell lines. Two of the evaluated compounds displayed significant in vitro activity (IC
50: 0.44–5.9
μM) comparable to that of the reference drug etoposide. |
| doi_str_mv | 10.1016/j.bmc.2006.03.008 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_68017138</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0968089606002057</els_id><sourcerecordid>68017138</sourcerecordid><originalsourceid>FETCH-LOGICAL-c412t-c113bb35e44dc7e4abddc217e1fd545a6d090ed12bc00c178d750f5478ac68e43</originalsourceid><addsrcrecordid>eNqFkcuO1DAQRS0EYpqBD2CDvIFdQjl27ARWoxEvaSSQBtaWU64MbqXtJnYj8vek6Razg1Vtzj26qsvYcwG1AKFfb-thh3UDoGuQNUD3gG2E0qqSshcP2QZ63VXQ9fqCPcl5CwCN6sVjdiF0q6UxcsPubsvBB8o8Rf7jEGKKlGv-xc2FK_GG3y6xfKccMnfRc1xKKulXwFAWnkYecvqTmUKkClMsLsQQ7_g-TQsuOAX863zKHo1uyvTsfC_Zt_fvvl5_rG4-f_h0fXVToRJNqVAIOQyyJaU8GlJu8B4bYUiMvlWt0x56IC-aAQFQmM6bFsZWmc6h7kjJS_bq5N3PazfKxe5CRpomFykdstUdCCNk919wpUzXN0ejOIE4p5xnGu1-Djs3L1aAPc5gt3adwR5nsCDtOsOaeXGWH4Yd-fvE-e8r8PIMuIxuGmcXMeR7znRN22q9cm9PHK0_-xlothkDRSQfZsJifQr_qPEbHZKmtg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>17178924</pqid></control><display><type>article</type><title>Studies on quinones. Part 41: Synthesis and cytotoxicity of isoquinoline-containing polycyclic quinones</title><source>ScienceDirect Journals</source><creator>Valderrama, Jaime A. ; González, M. Florencia ; Pessoa-Mahana, David ; Tapia, Ricardo A. ; Fillion, Houda ; Pautet, Felix ; Rodriguez, Jaime A. ; Theoduloz, Cristina ; Schmeda-Hirschmann, Guillermo</creator><creatorcontrib>Valderrama, Jaime A. ; González, M. Florencia ; Pessoa-Mahana, David ; Tapia, Ricardo A. ; Fillion, Houda ; Pautet, Felix ; Rodriguez, Jaime A. ; Theoduloz, Cristina ; Schmeda-Hirschmann, Guillermo</creatorcontrib><description>The regioselective synthesis of fused isoquinolinequinones (i.e.,
6,
8,
13, and
15) through highly regiocontrolled cycloaddition reactions from methyl 1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate
3 and 1,3-dienes is reported. The 2-aza- and 1,6-diaza-anthraquinone derivatives displayed significant in vitro activity on normal fibroblast and four tumor cell lines.
In the search for new potentially anticancer drugs, isoquinolinequinone-containing polycyclic compounds have been designed and synthesized through highly regiocontrolled cycloaddition reactions of methyl 1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate with polarized 1,3-dienes and a thiazole-
o-quinodimethane. The new
N-heterocyclic quinones were tested on normal human fibroblasts and four distinct human cancer cell lines. Two of the evaluated compounds displayed significant in vitro activity (IC
50: 0.44–5.9
μM) comparable to that of the reference drug etoposide.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2006.03.008</identifier><identifier>PMID: 16563773</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Aza-anthraquinones ; Biological and medical sciences ; Cell Line ; Cell Line, Tumor ; Cytotoxicity ; Diels–Alder reaction ; Drug Design ; Drug Screening Assays, Antitumor ; Etoposide - pharmacology ; Fibroblasts - drug effects ; General aspects ; Humans ; Medical sciences ; Pharmacology. Drug treatments ; Quinones - chemical synthesis ; Quinones - chemistry ; Quinones - pharmacology ; Regioselectivity</subject><ispartof>Bioorganic & medicinal chemistry, 2006-07, Vol.14 (14), p.5003-5011</ispartof><rights>2006 Elsevier Ltd</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c412t-c113bb35e44dc7e4abddc217e1fd545a6d090ed12bc00c178d750f5478ac68e43</citedby></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=17825566$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16563773$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Valderrama, Jaime A.</creatorcontrib><creatorcontrib>González, M. Florencia</creatorcontrib><creatorcontrib>Pessoa-Mahana, David</creatorcontrib><creatorcontrib>Tapia, Ricardo A.</creatorcontrib><creatorcontrib>Fillion, Houda</creatorcontrib><creatorcontrib>Pautet, Felix</creatorcontrib><creatorcontrib>Rodriguez, Jaime A.</creatorcontrib><creatorcontrib>Theoduloz, Cristina</creatorcontrib><creatorcontrib>Schmeda-Hirschmann, Guillermo</creatorcontrib><title>Studies on quinones. Part 41: Synthesis and cytotoxicity of isoquinoline-containing polycyclic quinones</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>The regioselective synthesis of fused isoquinolinequinones (i.e.,
6,
8,
13, and
15) through highly regiocontrolled cycloaddition reactions from methyl 1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate
3 and 1,3-dienes is reported. The 2-aza- and 1,6-diaza-anthraquinone derivatives displayed significant in vitro activity on normal fibroblast and four tumor cell lines.
In the search for new potentially anticancer drugs, isoquinolinequinone-containing polycyclic compounds have been designed and synthesized through highly regiocontrolled cycloaddition reactions of methyl 1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate with polarized 1,3-dienes and a thiazole-
o-quinodimethane. The new
N-heterocyclic quinones were tested on normal human fibroblasts and four distinct human cancer cell lines. Two of the evaluated compounds displayed significant in vitro activity (IC
50: 0.44–5.9
μM) comparable to that of the reference drug etoposide.</description><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Aza-anthraquinones</subject><subject>Biological and medical sciences</subject><subject>Cell Line</subject><subject>Cell Line, Tumor</subject><subject>Cytotoxicity</subject><subject>Diels–Alder reaction</subject><subject>Drug Design</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Etoposide - pharmacology</subject><subject>Fibroblasts - drug effects</subject><subject>General aspects</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Quinones - chemical synthesis</subject><subject>Quinones - chemistry</subject><subject>Quinones - pharmacology</subject><subject>Regioselectivity</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNqFkcuO1DAQRS0EYpqBD2CDvIFdQjl27ARWoxEvaSSQBtaWU64MbqXtJnYj8vek6Razg1Vtzj26qsvYcwG1AKFfb-thh3UDoGuQNUD3gG2E0qqSshcP2QZ63VXQ9fqCPcl5CwCN6sVjdiF0q6UxcsPubsvBB8o8Rf7jEGKKlGv-xc2FK_GG3y6xfKccMnfRc1xKKulXwFAWnkYecvqTmUKkClMsLsQQ7_g-TQsuOAX863zKHo1uyvTsfC_Zt_fvvl5_rG4-f_h0fXVToRJNqVAIOQyyJaU8GlJu8B4bYUiMvlWt0x56IC-aAQFQmM6bFsZWmc6h7kjJS_bq5N3PazfKxe5CRpomFykdstUdCCNk919wpUzXN0ejOIE4p5xnGu1-Djs3L1aAPc5gt3adwR5nsCDtOsOaeXGWH4Yd-fvE-e8r8PIMuIxuGmcXMeR7znRN22q9cm9PHK0_-xlothkDRSQfZsJifQr_qPEbHZKmtg</recordid><startdate>20060715</startdate><enddate>20060715</enddate><creator>Valderrama, Jaime A.</creator><creator>González, M. Florencia</creator><creator>Pessoa-Mahana, David</creator><creator>Tapia, Ricardo A.</creator><creator>Fillion, Houda</creator><creator>Pautet, Felix</creator><creator>Rodriguez, Jaime A.</creator><creator>Theoduloz, Cristina</creator><creator>Schmeda-Hirschmann, Guillermo</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20060715</creationdate><title>Studies on quinones. Part 41: Synthesis and cytotoxicity of isoquinoline-containing polycyclic quinones</title><author>Valderrama, Jaime A. ; González, M. Florencia ; Pessoa-Mahana, David ; Tapia, Ricardo A. ; Fillion, Houda ; Pautet, Felix ; Rodriguez, Jaime A. ; Theoduloz, Cristina ; Schmeda-Hirschmann, Guillermo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c412t-c113bb35e44dc7e4abddc217e1fd545a6d090ed12bc00c178d750f5478ac68e43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Aza-anthraquinones</topic><topic>Biological and medical sciences</topic><topic>Cell Line</topic><topic>Cell Line, Tumor</topic><topic>Cytotoxicity</topic><topic>Diels–Alder reaction</topic><topic>Drug Design</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Etoposide - pharmacology</topic><topic>Fibroblasts - drug effects</topic><topic>General aspects</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Quinones - chemical synthesis</topic><topic>Quinones - chemistry</topic><topic>Quinones - pharmacology</topic><topic>Regioselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Valderrama, Jaime A.</creatorcontrib><creatorcontrib>González, M. Florencia</creatorcontrib><creatorcontrib>Pessoa-Mahana, David</creatorcontrib><creatorcontrib>Tapia, Ricardo A.</creatorcontrib><creatorcontrib>Fillion, Houda</creatorcontrib><creatorcontrib>Pautet, Felix</creatorcontrib><creatorcontrib>Rodriguez, Jaime A.</creatorcontrib><creatorcontrib>Theoduloz, Cristina</creatorcontrib><creatorcontrib>Schmeda-Hirschmann, Guillermo</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>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Valderrama, Jaime A.</au><au>González, M. Florencia</au><au>Pessoa-Mahana, David</au><au>Tapia, Ricardo A.</au><au>Fillion, Houda</au><au>Pautet, Felix</au><au>Rodriguez, Jaime A.</au><au>Theoduloz, Cristina</au><au>Schmeda-Hirschmann, Guillermo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Studies on quinones. Part 41: Synthesis and cytotoxicity of isoquinoline-containing polycyclic quinones</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2006-07-15</date><risdate>2006</risdate><volume>14</volume><issue>14</issue><spage>5003</spage><epage>5011</epage><pages>5003-5011</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>The regioselective synthesis of fused isoquinolinequinones (i.e.,
6,
8,
13, and
15) through highly regiocontrolled cycloaddition reactions from methyl 1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate
3 and 1,3-dienes is reported. The 2-aza- and 1,6-diaza-anthraquinone derivatives displayed significant in vitro activity on normal fibroblast and four tumor cell lines.
In the search for new potentially anticancer drugs, isoquinolinequinone-containing polycyclic compounds have been designed and synthesized through highly regiocontrolled cycloaddition reactions of methyl 1,3-dimethyl-5,8-dioxo-5,8-dihydroisoquinoline-4-carboxylate with polarized 1,3-dienes and a thiazole-
o-quinodimethane. The new
N-heterocyclic quinones were tested on normal human fibroblasts and four distinct human cancer cell lines. Two of the evaluated compounds displayed significant in vitro activity (IC
50: 0.44–5.9
μM) comparable to that of the reference drug etoposide.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16563773</pmid><doi>10.1016/j.bmc.2006.03.008</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2006-07, Vol.14 (14), p.5003-5011 |
| issn | 0968-0896 1464-3391 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_68017138 |
| source | ScienceDirect Journals |
| subjects | Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Aza-anthraquinones Biological and medical sciences Cell Line Cell Line, Tumor Cytotoxicity Diels–Alder reaction Drug Design Drug Screening Assays, Antitumor Etoposide - pharmacology Fibroblasts - drug effects General aspects Humans Medical sciences Pharmacology. Drug treatments Quinones - chemical synthesis Quinones - chemistry Quinones - pharmacology Regioselectivity |
| title | Studies on quinones. Part 41: Synthesis and cytotoxicity of isoquinoline-containing polycyclic quinones |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T00%3A07%3A42IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Studies%20on%20quinones.%20Part%2041:%20Synthesis%20and%20cytotoxicity%20of%20isoquinoline-containing%20polycyclic%20quinones&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry&rft.au=Valderrama,%20Jaime%20A.&rft.date=2006-07-15&rft.volume=14&rft.issue=14&rft.spage=5003&rft.epage=5011&rft.pages=5003-5011&rft.issn=0968-0896&rft.eissn=1464-3391&rft_id=info:doi/10.1016/j.bmc.2006.03.008&rft_dat=%3Cproquest_cross%3E68017138%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c412t-c113bb35e44dc7e4abddc217e1fd545a6d090ed12bc00c178d750f5478ac68e43%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=17178924&rft_id=info:pmid/16563773&rfr_iscdi=true |