Synthesis of Novel Rhinacanthins and Related Anticancer Naphthoquinone Esters
Rhinacanthin-M, -N and -Q, natural products isolated from the medicinal plant Rhinacanthus nasutus, and 39 novel naphthoquinone esters have been synthesized in excellent yield by esterification of naphthoquinone-3-(propan-3‘-ols) with benzoic or naphthoic acids. Almost all the naphthoquinone esters...
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| Veröffentlicht in: | Journal of medicinal chemistry 2004-08, Vol.47 (18), p.4427-4438 |
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| container_title | Journal of medicinal chemistry |
| container_volume | 47 |
| creator | Kongkathip, Ngampong Luangkamin, Suwaporn Kongkathip, Boonsong Sangma, Chak Grigg, Ronald Kongsaeree, Palangpon Prabpai, Samran Pradidphol, Narathip Piyaviriyagul, Suratsawadee Siripong, Pongpun |
| description | Rhinacanthin-M, -N and -Q, natural products isolated from the medicinal plant Rhinacanthus nasutus, and 39 novel naphthoquinone esters have been synthesized in excellent yield by esterification of naphthoquinone-3-(propan-3‘-ols) with benzoic or naphthoic acids. Almost all the naphthoquinone esters that contain a C-3 hydroxy group showed significant cytotoxicities against KB, HeLa, and HepG2 cell lines. In contrast, ester derivatives lacking the C-3 hydroxy group were inactive to the cancer cell lines. Two methyl substituents on the C-2‘ of propyl chain conferred more potent cytotoxicity than when there is only one or no methyl group. Naphthoate esters exhibited greater cytotoxicity than benzoate esters. Computer modeling has been done to obtain a first look at the mode of action in connection with these observations. |
| doi_str_mv | 10.1021/jm030323g |
| format | Article |
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Almost all the naphthoquinone esters that contain a C-3 hydroxy group showed significant cytotoxicities against KB, HeLa, and HepG2 cell lines. In contrast, ester derivatives lacking the C-3 hydroxy group were inactive to the cancer cell lines. Two methyl substituents on the C-2‘ of propyl chain conferred more potent cytotoxicity than when there is only one or no methyl group. Naphthoate esters exhibited greater cytotoxicity than benzoate esters. Computer modeling has been done to obtain a first look at the mode of action in connection with these observations.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm030323g</identifier><identifier>PMID: 15317455</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Antineoplastic agents ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Binding Sites ; Biological and medical sciences ; Cell Division - drug effects ; Cell Line, Tumor ; Doxorubicin - chemistry ; Esters - chemical synthesis ; Esters - pharmacology ; General aspects ; General pharmacology ; Humans ; Inhibitory Concentration 50 ; Medical sciences ; Models, Molecular ; Naphthoquinones - chemical synthesis ; Naphthoquinones - pharmacology ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Rhinacanthus nasutus ; Structure-Activity Relationship ; Topoisomerase II Inhibitors</subject><ispartof>Journal of medicinal chemistry, 2004-08, Vol.47 (18), p.4427-4438</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a476t-96c7e2784559c23c1693aead93c76a9a191a5a067b5b59e539a077708c0e1d903</citedby><cites>FETCH-LOGICAL-a476t-96c7e2784559c23c1693aead93c76a9a191a5a067b5b59e539a077708c0e1d903</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/jm030323g$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm030323g$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16040964$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15317455$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kongkathip, Ngampong</creatorcontrib><creatorcontrib>Luangkamin, Suwaporn</creatorcontrib><creatorcontrib>Kongkathip, Boonsong</creatorcontrib><creatorcontrib>Sangma, Chak</creatorcontrib><creatorcontrib>Grigg, Ronald</creatorcontrib><creatorcontrib>Kongsaeree, Palangpon</creatorcontrib><creatorcontrib>Prabpai, Samran</creatorcontrib><creatorcontrib>Pradidphol, Narathip</creatorcontrib><creatorcontrib>Piyaviriyagul, Suratsawadee</creatorcontrib><creatorcontrib>Siripong, Pongpun</creatorcontrib><title>Synthesis of Novel Rhinacanthins and Related Anticancer Naphthoquinone Esters</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Rhinacanthin-M, -N and -Q, natural products isolated from the medicinal plant Rhinacanthus nasutus, and 39 novel naphthoquinone esters have been synthesized in excellent yield by esterification of naphthoquinone-3-(propan-3‘-ols) with benzoic or naphthoic acids. Almost all the naphthoquinone esters that contain a C-3 hydroxy group showed significant cytotoxicities against KB, HeLa, and HepG2 cell lines. In contrast, ester derivatives lacking the C-3 hydroxy group were inactive to the cancer cell lines. Two methyl substituents on the C-2‘ of propyl chain conferred more potent cytotoxicity than when there is only one or no methyl group. Naphthoate esters exhibited greater cytotoxicity than benzoate esters. Computer modeling has been done to obtain a first look at the mode of action in connection with these observations.</description><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Binding Sites</subject><subject>Biological and medical sciences</subject><subject>Cell Division - drug effects</subject><subject>Cell Line, Tumor</subject><subject>Doxorubicin - chemistry</subject><subject>Esters - chemical synthesis</subject><subject>Esters - pharmacology</subject><subject>General aspects</subject><subject>General pharmacology</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Naphthoquinones - chemical synthesis</subject><subject>Naphthoquinones - pharmacology</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Rhinacanthus nasutus</subject><subject>Structure-Activity Relationship</subject><subject>Topoisomerase II Inhibitors</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkE1vEzEQhi0EomnhwB9AewGph4WxvbbjY1UVWpQG6IfUmzXxThqnG2-wNxX99zVK1Fw4jTTzzKtXD2MfOHzhIPjX5QokSCHvX7ERVwLqZgzNazYCEKIWWsgDdpjzEgAkF_ItO-BKctMoNWKX109xWFAOuern1bR_pK66WoSIHss-xFxhbKsr6nCgtjqJQygHT6ma4noxLPo_mxD7SNVZHijld-zNHLtM73fziN1-O7s5Pa8nP79fnJ5MamyMHmqrvSFhxqWB9UJ6rq1EwtZKbzRa5JajQtBmpmbKkpIWwRgDYw_EWwvyiH3e5q5TaUB5cKuQPXUdRuo32XHbmKZ8FPB4C_rU55xo7tYprDA9OQ7unzv34q6wH3ehm9mK2j25k1WATzsAs8dunoqJkPechgasbgpXb7lQpPx9uWN6cNpIo9zNr2s3VXeX0v7-4Sb7XPTZLftNisXdfwo-AyULkKM</recordid><startdate>20040826</startdate><enddate>20040826</enddate><creator>Kongkathip, Ngampong</creator><creator>Luangkamin, Suwaporn</creator><creator>Kongkathip, Boonsong</creator><creator>Sangma, Chak</creator><creator>Grigg, Ronald</creator><creator>Kongsaeree, Palangpon</creator><creator>Prabpai, Samran</creator><creator>Pradidphol, Narathip</creator><creator>Piyaviriyagul, Suratsawadee</creator><creator>Siripong, Pongpun</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20040826</creationdate><title>Synthesis of Novel Rhinacanthins and Related Anticancer Naphthoquinone Esters</title><author>Kongkathip, Ngampong ; Luangkamin, Suwaporn ; Kongkathip, Boonsong ; Sangma, Chak ; Grigg, Ronald ; Kongsaeree, Palangpon ; Prabpai, Samran ; Pradidphol, Narathip ; Piyaviriyagul, Suratsawadee ; Siripong, Pongpun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a476t-96c7e2784559c23c1693aead93c76a9a191a5a067b5b59e539a077708c0e1d903</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Binding Sites</topic><topic>Biological and medical sciences</topic><topic>Cell Division - drug effects</topic><topic>Cell Line, Tumor</topic><topic>Doxorubicin - chemistry</topic><topic>Esters - chemical synthesis</topic><topic>Esters - pharmacology</topic><topic>General aspects</topic><topic>General pharmacology</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Naphthoquinones - chemical synthesis</topic><topic>Naphthoquinones - pharmacology</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Rhinacanthus nasutus</topic><topic>Structure-Activity Relationship</topic><topic>Topoisomerase II Inhibitors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kongkathip, Ngampong</creatorcontrib><creatorcontrib>Luangkamin, Suwaporn</creatorcontrib><creatorcontrib>Kongkathip, Boonsong</creatorcontrib><creatorcontrib>Sangma, Chak</creatorcontrib><creatorcontrib>Grigg, Ronald</creatorcontrib><creatorcontrib>Kongsaeree, Palangpon</creatorcontrib><creatorcontrib>Prabpai, Samran</creatorcontrib><creatorcontrib>Pradidphol, Narathip</creatorcontrib><creatorcontrib>Piyaviriyagul, Suratsawadee</creatorcontrib><creatorcontrib>Siripong, Pongpun</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>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kongkathip, Ngampong</au><au>Luangkamin, Suwaporn</au><au>Kongkathip, Boonsong</au><au>Sangma, Chak</au><au>Grigg, Ronald</au><au>Kongsaeree, Palangpon</au><au>Prabpai, Samran</au><au>Pradidphol, Narathip</au><au>Piyaviriyagul, Suratsawadee</au><au>Siripong, Pongpun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Novel Rhinacanthins and Related Anticancer Naphthoquinone Esters</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2004-08-26</date><risdate>2004</risdate><volume>47</volume><issue>18</issue><spage>4427</spage><epage>4438</epage><pages>4427-4438</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>Rhinacanthin-M, -N and -Q, natural products isolated from the medicinal plant Rhinacanthus nasutus, and 39 novel naphthoquinone esters have been synthesized in excellent yield by esterification of naphthoquinone-3-(propan-3‘-ols) with benzoic or naphthoic acids. Almost all the naphthoquinone esters that contain a C-3 hydroxy group showed significant cytotoxicities against KB, HeLa, and HepG2 cell lines. In contrast, ester derivatives lacking the C-3 hydroxy group were inactive to the cancer cell lines. Two methyl substituents on the C-2‘ of propyl chain conferred more potent cytotoxicity than when there is only one or no methyl group. Naphthoate esters exhibited greater cytotoxicity than benzoate esters. Computer modeling has been done to obtain a first look at the mode of action in connection with these observations.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15317455</pmid><doi>10.1021/jm030323g</doi><tpages>12</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 2004-08, Vol.47 (18), p.4427-4438 |
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| subjects | Antineoplastic agents Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Binding Sites Biological and medical sciences Cell Division - drug effects Cell Line, Tumor Doxorubicin - chemistry Esters - chemical synthesis Esters - pharmacology General aspects General pharmacology Humans Inhibitory Concentration 50 Medical sciences Models, Molecular Naphthoquinones - chemical synthesis Naphthoquinones - pharmacology Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Rhinacanthus nasutus Structure-Activity Relationship Topoisomerase II Inhibitors |
| title | Synthesis of Novel Rhinacanthins and Related Anticancer Naphthoquinone Esters |
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