Antitumor Activity of Novel Deoxoartemisinin Monomers, Dimers, and Trimer
The first primary amines 9 and bromoalkyl analogues 7 of deoxoartemisinin with nonacetal functionality at C-12 are prepared as versatile intermediates for the synthesis of various derivatives. Eight C-12 nonacetal type dimers and one trimer of deoxoartemisinin were prepared using novel chemistry. Di...
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| Veröffentlicht in: | Journal of medicinal chemistry 2003-03, Vol.46 (6), p.987-994 |
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| container_end_page | 994 |
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| container_issue | 6 |
| container_start_page | 987 |
| container_title | Journal of medicinal chemistry |
| container_volume | 46 |
| creator | Jung, Mankil Lee, Sangmin Ham, Jungyeob Lee, Kyunghoon Kim, Hanjo Kim, Soo Kie |
| description | The first primary amines 9 and bromoalkyl analogues 7 of deoxoartemisinin with nonacetal functionality at C-12 are prepared as versatile intermediates for the synthesis of various derivatives. Eight C-12 nonacetal type dimers and one trimer of deoxoartemisinin were prepared using novel chemistry. Dimers, particularly 12a, 18a,b, and trimer 17, were especially potent and selective at inhibiting the growth of certain human cancer cell lines and were comparable to that of clinically used anticancer drugs. The linker with one amide- or one sulfur-centered two ethylene groups of the dimers is essential for high anticancer activity. Trimer 17 shows very potent activity against most of the human cancer cell lines tested. |
| doi_str_mv | 10.1021/jm020119d |
| format | Article |
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Eight C-12 nonacetal type dimers and one trimer of deoxoartemisinin were prepared using novel chemistry. Dimers, particularly 12a, 18a,b, and trimer 17, were especially potent and selective at inhibiting the growth of certain human cancer cell lines and were comparable to that of clinically used anticancer drugs. The linker with one amide- or one sulfur-centered two ethylene groups of the dimers is essential for high anticancer activity. Trimer 17 shows very potent activity against most of the human cancer cell lines tested.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm020119d</identifier><identifier>PMID: 12620075</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Artemisinins - chemical synthesis ; Artemisinins - chemistry ; Artemisinins - pharmacology ; Biological and medical sciences ; Drug Screening Assays, Antitumor ; General aspects ; Humans ; Medical sciences ; Mice ; Pharmacology. Drug treatments ; Polymers ; Sesquiterpenes - chemical synthesis ; Sesquiterpenes - chemistry ; Sesquiterpenes - pharmacology ; Structure-Activity Relationship ; Tumor Cells, Cultured</subject><ispartof>Journal of medicinal chemistry, 2003-03, Vol.46 (6), p.987-994</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-e19e38508fd97ef5fb5d6c6b76c61c250693b8c3f1f8065ba0e540bc97d35ea03</citedby><cites>FETCH-LOGICAL-a445t-e19e38508fd97ef5fb5d6c6b76c61c250693b8c3f1f8065ba0e540bc97d35ea03</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/jm020119d$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm020119d$$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=14640152$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12620075$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jung, Mankil</creatorcontrib><creatorcontrib>Lee, Sangmin</creatorcontrib><creatorcontrib>Ham, Jungyeob</creatorcontrib><creatorcontrib>Lee, Kyunghoon</creatorcontrib><creatorcontrib>Kim, Hanjo</creatorcontrib><creatorcontrib>Kim, Soo Kie</creatorcontrib><title>Antitumor Activity of Novel Deoxoartemisinin Monomers, Dimers, and Trimer</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>The first primary amines 9 and bromoalkyl analogues 7 of deoxoartemisinin with nonacetal functionality at C-12 are prepared as versatile intermediates for the synthesis of various derivatives. Eight C-12 nonacetal type dimers and one trimer of deoxoartemisinin were prepared using novel chemistry. Dimers, particularly 12a, 18a,b, and trimer 17, were especially potent and selective at inhibiting the growth of certain human cancer cell lines and were comparable to that of clinically used anticancer drugs. The linker with one amide- or one sulfur-centered two ethylene groups of the dimers is essential for high anticancer activity. Trimer 17 shows very potent activity against most of the human cancer cell lines tested.</description><subject>Animals</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Artemisinins - chemical synthesis</subject><subject>Artemisinins - chemistry</subject><subject>Artemisinins - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General aspects</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Pharmacology. Drug treatments</subject><subject>Polymers</subject><subject>Sesquiterpenes - chemical synthesis</subject><subject>Sesquiterpenes - chemistry</subject><subject>Sesquiterpenes - pharmacology</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>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtKAzEUhoMotl4WvoDMRkFw9CSZzGVZWm9gq2AFdyGTSSB1ZqLJTLFvb0qL3bg5h5N8_Px8CJ1huMFA8O2iAQIYF9UeGmJGIE5ySPbREICQmKSEDtCR9wsAoJjQQzTA4REgY0P0NGo70_WNddFIdmZpulVkdTSzS1VHE2V_rHCdaow3rWmjqW1to5y_jiZms0VbRXO3Pk7QgRa1V6fbfYze7-_m48f4-eXhaTx6jkWSsC5WuFA0Z5DrqsiUZrpkVSrTMgsDS8IgLWiZS6qxziFlpQDFEihlkVWUKQH0GF1ucr-c_e6V73hoJ1Vdi1bZ3vOMQo4pYQG82oDSWe-d0vwrFBVuxTHwtTf-5y2w59vQvmxUtSO3ogJwsQWEl6LWTrTS-B2XpAkE9YGLN5zxnfr5-xfuk6cZzRifv75xAhPyMZ4SPtvlCun5wvauDe7-KfgLv5CPPw</recordid><startdate>20030313</startdate><enddate>20030313</enddate><creator>Jung, Mankil</creator><creator>Lee, Sangmin</creator><creator>Ham, Jungyeob</creator><creator>Lee, Kyunghoon</creator><creator>Kim, Hanjo</creator><creator>Kim, Soo Kie</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>20030313</creationdate><title>Antitumor Activity of Novel Deoxoartemisinin Monomers, Dimers, and Trimer</title><author>Jung, Mankil ; Lee, Sangmin ; Ham, Jungyeob ; Lee, Kyunghoon ; Kim, Hanjo ; Kim, Soo Kie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-e19e38508fd97ef5fb5d6c6b76c61c250693b8c3f1f8065ba0e540bc97d35ea03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Animals</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Artemisinins - chemical synthesis</topic><topic>Artemisinins - chemistry</topic><topic>Artemisinins - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General aspects</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Pharmacology. Drug treatments</topic><topic>Polymers</topic><topic>Sesquiterpenes - chemical synthesis</topic><topic>Sesquiterpenes - chemistry</topic><topic>Sesquiterpenes - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jung, Mankil</creatorcontrib><creatorcontrib>Lee, Sangmin</creatorcontrib><creatorcontrib>Ham, Jungyeob</creatorcontrib><creatorcontrib>Lee, Kyunghoon</creatorcontrib><creatorcontrib>Kim, Hanjo</creatorcontrib><creatorcontrib>Kim, Soo Kie</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>Jung, Mankil</au><au>Lee, Sangmin</au><au>Ham, Jungyeob</au><au>Lee, Kyunghoon</au><au>Kim, Hanjo</au><au>Kim, Soo Kie</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antitumor Activity of Novel Deoxoartemisinin Monomers, Dimers, and Trimer</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. 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| ispartof | Journal of medicinal chemistry, 2003-03, Vol.46 (6), p.987-994 |
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| subjects | Animals Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Artemisinins - chemical synthesis Artemisinins - chemistry Artemisinins - pharmacology Biological and medical sciences Drug Screening Assays, Antitumor General aspects Humans Medical sciences Mice Pharmacology. Drug treatments Polymers Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Sesquiterpenes - pharmacology Structure-Activity Relationship Tumor Cells, Cultured |
| title | Antitumor Activity of Novel Deoxoartemisinin Monomers, Dimers, and Trimer |
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