Antitumor Agents. 166. Synthesis and Biological Evaluation of 5,6,7,8-Substituted-2-phenylthiochromen-4-ones
As a continuation of our structure−activity relationship study of substituted 2-phenyl-4-quinolones and flavonoids as antitumor and antiviral agents, a series of 5,6,7,8-substituted-2-phenylthiochromen-4-ones has been synthesized by condensation of substituted thiophenols and ethyl benzoylacetates....
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| Veröffentlicht in: | Journal of medicinal chemistry 1996-05, Vol.39 (10), p.1975-1980 |
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| container_end_page | 1980 |
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| container_issue | 10 |
| container_start_page | 1975 |
| container_title | Journal of medicinal chemistry |
| container_volume | 39 |
| creator | Wang, Hui-Kang Bastow, Kenneth F Cosentino, L. Mark Lee, Kuo-Hsiung |
| description | As a continuation of our structure−activity relationship study of substituted 2-phenyl-4-quinolones and flavonoids as antitumor and antiviral agents, a series of 5,6,7,8-substituted-2-phenylthiochromen-4-ones has been synthesized by condensation of substituted thiophenols and ethyl benzoylacetates. Target compounds were evaluated for biological activity. Among them, compounds 7, 10, 12, and 13 displayed significant growth inhibitory action against a panel of tumor cell lines including human ileocecal carcinoma (HCT-8), murine leukemia (P-388), human melanoma (RPMI), and human central nervous system tumor (TE671) cells. Compounds 10, 12, and 19 displayed DNA topoisomerase I inhibitory activity in vitro and compound 11 was an in vitro, inhibitor of DNA topoisomerase II. Compound 11 was most active (ED50 value, 0.65 μM) against HIV in acutely infected H9 lymphocytes and had a therapeutic index of about 5. |
| doi_str_mv | 10.1021/jm960008c |
| format | Article |
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Synthesis and Biological Evaluation of 5,6,7,8-Substituted-2-phenylthiochromen-4-ones</title><source>ACS Publications</source><source>MEDLINE</source><creator>Wang, Hui-Kang ; Bastow, Kenneth F ; Cosentino, L. Mark ; Lee, Kuo-Hsiung</creator><creatorcontrib>Wang, Hui-Kang ; Bastow, Kenneth F ; Cosentino, L. Mark ; Lee, Kuo-Hsiung</creatorcontrib><description>As a continuation of our structure−activity relationship study of substituted 2-phenyl-4-quinolones and flavonoids as antitumor and antiviral agents, a series of 5,6,7,8-substituted-2-phenylthiochromen-4-ones has been synthesized by condensation of substituted thiophenols and ethyl benzoylacetates. Target compounds were evaluated for biological activity. Among them, compounds 7, 10, 12, and 13 displayed significant growth inhibitory action against a panel of tumor cell lines including human ileocecal carcinoma (HCT-8), murine leukemia (P-388), human melanoma (RPMI), and human central nervous system tumor (TE671) cells. Compounds 10, 12, and 19 displayed DNA topoisomerase I inhibitory activity in vitro and compound 11 was an in vitro, inhibitor of DNA topoisomerase II. Compound 11 was most active (ED50 value, 0.65 μM) against HIV in acutely infected H9 lymphocytes and had a therapeutic index of about 5.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm960008c</identifier><identifier>PMID: 8642556</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>AIDS/HIV ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Biological and medical sciences ; Cell Line ; Chromans - chemical synthesis ; Chromans - chemistry ; Chromans - pharmacology ; General aspects ; HIV - drug effects ; Humans ; Magnetic Resonance Spectroscopy ; Medical sciences ; Pharmacology. Drug treatments ; Structure-Activity Relationship ; Tumor Cells, Cultured</subject><ispartof>Journal of medicinal chemistry, 1996-05, Vol.39 (10), p.1975-1980</ispartof><rights>Copyright © 1996 American Chemical Society</rights><rights>1996 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a443t-bfec5c5b2ce54f033777fe9dc5828a261fa404a75f6c6aa0ab930eaccb25a6a03</citedby><cites>FETCH-LOGICAL-a443t-bfec5c5b2ce54f033777fe9dc5828a261fa404a75f6c6aa0ab930eaccb25a6a03</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/jm960008c$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm960008c$$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=3088259$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8642556$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Hui-Kang</creatorcontrib><creatorcontrib>Bastow, Kenneth F</creatorcontrib><creatorcontrib>Cosentino, L. Mark</creatorcontrib><creatorcontrib>Lee, Kuo-Hsiung</creatorcontrib><title>Antitumor Agents. 166. Synthesis and Biological Evaluation of 5,6,7,8-Substituted-2-phenylthiochromen-4-ones</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>As a continuation of our structure−activity relationship study of substituted 2-phenyl-4-quinolones and flavonoids as antitumor and antiviral agents, a series of 5,6,7,8-substituted-2-phenylthiochromen-4-ones has been synthesized by condensation of substituted thiophenols and ethyl benzoylacetates. Target compounds were evaluated for biological activity. Among them, compounds 7, 10, 12, and 13 displayed significant growth inhibitory action against a panel of tumor cell lines including human ileocecal carcinoma (HCT-8), murine leukemia (P-388), human melanoma (RPMI), and human central nervous system tumor (TE671) cells. Compounds 10, 12, and 19 displayed DNA topoisomerase I inhibitory activity in vitro and compound 11 was an in vitro, inhibitor of DNA topoisomerase II. Compound 11 was most active (ED50 value, 0.65 μM) against HIV in acutely infected H9 lymphocytes and had a therapeutic index of about 5.</description><subject>AIDS/HIV</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cell Line</subject><subject>Chromans - chemical synthesis</subject><subject>Chromans - chemistry</subject><subject>Chromans - pharmacology</subject><subject>General aspects</subject><subject>HIV - drug effects</subject><subject>Humans</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Pharmacology. Drug treatments</subject><subject>Structure-Activity Relationship</subject><subject>Tumor Cells, Cultured</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E-LEzEYx_EgytpdPfgChDmoIDQ1_2d6rMu6u7Cg0Kqwl_BMmmxTZ5KaZGT77p2lpac95fB8-BG-CL2jZEYJo1-2_VwRQhrzAk2oZASLhoiXaEIIY5gpxl-j85y3I-GU8TN01ijBpFQT1C1C8WXoY6oWDzaUPKuoUrNquQ9lY7PPFYR19dXHLj54A1119Q-6AYqPoYquklM1racNXg5tftopdo0Z3m1s2Hdl46PZpNjbgAWOweY36JWDLtu3x_cC_fx2tbq8wXffr28vF3cYhOAFt84aaWTLjJXCEc7runZ2vjayYQ0wRR0IIqCWThkFQKCdc2LBmJZJUED4Bfp02N2l-HewuejeZ2O7DoKNQ9b1WKchko_w8wGaFHNO1uld8j2kvaZEP5XVp7KjfX8cHdrerk_ymHK8fzjeIY-hXIJgfD4xTpqGyfnI8IH5XOzj6Qzpj1Y1r6Ve_Vjqe75i6je9179G__HgwWS9jUMKY7lnvvcfS0qbCg</recordid><startdate>19960510</startdate><enddate>19960510</enddate><creator>Wang, Hui-Kang</creator><creator>Bastow, Kenneth F</creator><creator>Cosentino, L. Mark</creator><creator>Lee, Kuo-Hsiung</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>19960510</creationdate><title>Antitumor Agents. 166. Synthesis and Biological Evaluation of 5,6,7,8-Substituted-2-phenylthiochromen-4-ones</title><author>Wang, Hui-Kang ; Bastow, Kenneth F ; Cosentino, L. Mark ; Lee, Kuo-Hsiung</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a443t-bfec5c5b2ce54f033777fe9dc5828a261fa404a75f6c6aa0ab930eaccb25a6a03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>AIDS/HIV</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Line</topic><topic>Chromans - chemical synthesis</topic><topic>Chromans - chemistry</topic><topic>Chromans - pharmacology</topic><topic>General aspects</topic><topic>HIV - drug effects</topic><topic>Humans</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Pharmacology. Drug treatments</topic><topic>Structure-Activity Relationship</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Hui-Kang</creatorcontrib><creatorcontrib>Bastow, Kenneth F</creatorcontrib><creatorcontrib>Cosentino, L. Mark</creatorcontrib><creatorcontrib>Lee, Kuo-Hsiung</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>Wang, Hui-Kang</au><au>Bastow, Kenneth F</au><au>Cosentino, L. Mark</au><au>Lee, Kuo-Hsiung</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antitumor Agents. 166. Synthesis and Biological Evaluation of 5,6,7,8-Substituted-2-phenylthiochromen-4-ones</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1996-05-10</date><risdate>1996</risdate><volume>39</volume><issue>10</issue><spage>1975</spage><epage>1980</epage><pages>1975-1980</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>As a continuation of our structure−activity relationship study of substituted 2-phenyl-4-quinolones and flavonoids as antitumor and antiviral agents, a series of 5,6,7,8-substituted-2-phenylthiochromen-4-ones has been synthesized by condensation of substituted thiophenols and ethyl benzoylacetates. Target compounds were evaluated for biological activity. Among them, compounds 7, 10, 12, and 13 displayed significant growth inhibitory action against a panel of tumor cell lines including human ileocecal carcinoma (HCT-8), murine leukemia (P-388), human melanoma (RPMI), and human central nervous system tumor (TE671) cells. Compounds 10, 12, and 19 displayed DNA topoisomerase I inhibitory activity in vitro and compound 11 was an in vitro, inhibitor of DNA topoisomerase II. Compound 11 was most active (ED50 value, 0.65 μM) against HIV in acutely infected H9 lymphocytes and had a therapeutic index of about 5.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>8642556</pmid><doi>10.1021/jm960008c</doi><tpages>6</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1996-05, Vol.39 (10), p.1975-1980 |
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| source | ACS Publications; MEDLINE |
| subjects | AIDS/HIV Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Biological and medical sciences Cell Line Chromans - chemical synthesis Chromans - chemistry Chromans - pharmacology General aspects HIV - drug effects Humans Magnetic Resonance Spectroscopy Medical sciences Pharmacology. Drug treatments Structure-Activity Relationship Tumor Cells, Cultured |
| title | Antitumor Agents. 166. Synthesis and Biological Evaluation of 5,6,7,8-Substituted-2-phenylthiochromen-4-ones |
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