Norcantharimides, synthesis and anticancer activity: Synthesis of new norcantharidin analogues and their anticancer evaluation
A range of amines was reacted with norcantharidin ( 2) to provide the corresponding norcantharimides ( 9– 43). Treatment of norcantharidin with allylamine afforded the corresponding allyl-norcantharimide ( 20) which was amenable to epoxidation (mCPBA, 22) and subsequent ring opening (MeOH/H +; 23) o...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2007-09, Vol.15 (18), p.6126-6134 |
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| container_title | Bioorganic & medicinal chemistry |
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| creator | Hill, Timothy A. Stewart, Scott G. Ackland, Stephen P. Gilbert, Jayne Sauer, Benjamin Sakoff, Jennette A. McCluskey, Adam |
| description | A range of amines was reacted with norcantharidin (
2) to provide the corresponding norcantharimides (
9–
43). Treatment of norcantharidin with allylamine afforded the corresponding allyl-norcantharimide (
20) which was amenable to epoxidation (mCPBA,
22) and subsequent ring opening (MeOH/H
+;
23) or alternatively, osmylation (OsO
4/NMO;
24). These simple synthetic modifications of
2 facilitated the development of a novel series of norcantharimides displaying modest to good broad spectrum cytotoxicity against HT29 and SW480 (colorectal carcinoma); MCF-7 (breast adenocarcinoma); A2780 (ovarian carcinoma); H460 (lung carcinoma); A431 (epidermoid carcinoma); DU145 (prostate carcinoma); BE2-C (neuroblastoma); and SJ-G2 (glioblastoma). Analogues possessing a C
10, C
12 or C
14 alkyl chain or a C
12 linked bis-norcantharimide displayed the highest levels of cytotoxicity. |
| doi_str_mv | 10.1016/j.bmc.2007.06.034 |
| format | Article |
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2) to provide the corresponding norcantharimides (
9–
43). Treatment of norcantharidin with allylamine afforded the corresponding allyl-norcantharimide (
20) which was amenable to epoxidation (mCPBA,
22) and subsequent ring opening (MeOH/H
+;
23) or alternatively, osmylation (OsO
4/NMO;
24). These simple synthetic modifications of
2 facilitated the development of a novel series of norcantharimides displaying modest to good broad spectrum cytotoxicity against HT29 and SW480 (colorectal carcinoma); MCF-7 (breast adenocarcinoma); A2780 (ovarian carcinoma); H460 (lung carcinoma); A431 (epidermoid carcinoma); DU145 (prostate carcinoma); BE2-C (neuroblastoma); and SJ-G2 (glioblastoma). Analogues possessing a C
10, C
12 or C
14 alkyl chain or a C
12 linked bis-norcantharimide displayed the highest levels of cytotoxicity.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2007.06.034</identifier><identifier>PMID: 17606377</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Anticancer ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis ; Bridged Bicyclo Compounds, Heterocyclic - chemistry ; Bridged Bicyclo Compounds, Heterocyclic - pharmacology ; Cantharidin ; Cytotoxicity ; Drug Screening Assays, Antitumor ; General aspects ; Humans ; Medical sciences ; Molecular Structure ; Neoplasms - drug therapy ; Neoplasms - pathology ; Norcantharidin ; Norcantharimides ; Pharmacology. Drug treatments ; Structure-Activity Relationship ; Tumor Cells, Cultured - drug effects</subject><ispartof>Bioorganic & medicinal chemistry, 2007-09, Vol.15 (18), p.6126-6134</ispartof><rights>2007</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c381t-4ca771d1e7c551552b1441e241a80954df951bb00523e3ce9a1d83506d572c8a3</citedby><cites>FETCH-LOGICAL-c381t-4ca771d1e7c551552b1441e241a80954df951bb00523e3ce9a1d83506d572c8a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2007.06.034$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18968832$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17606377$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hill, Timothy A.</creatorcontrib><creatorcontrib>Stewart, Scott G.</creatorcontrib><creatorcontrib>Ackland, Stephen P.</creatorcontrib><creatorcontrib>Gilbert, Jayne</creatorcontrib><creatorcontrib>Sauer, Benjamin</creatorcontrib><creatorcontrib>Sakoff, Jennette A.</creatorcontrib><creatorcontrib>McCluskey, Adam</creatorcontrib><title>Norcantharimides, synthesis and anticancer activity: Synthesis of new norcantharidin analogues and their anticancer evaluation</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A range of amines was reacted with norcantharidin (
2) to provide the corresponding norcantharimides (
9–
43). Treatment of norcantharidin with allylamine afforded the corresponding allyl-norcantharimide (
20) which was amenable to epoxidation (mCPBA,
22) and subsequent ring opening (MeOH/H
+;
23) or alternatively, osmylation (OsO
4/NMO;
24). These simple synthetic modifications of
2 facilitated the development of a novel series of norcantharimides displaying modest to good broad spectrum cytotoxicity against HT29 and SW480 (colorectal carcinoma); MCF-7 (breast adenocarcinoma); A2780 (ovarian carcinoma); H460 (lung carcinoma); A431 (epidermoid carcinoma); DU145 (prostate carcinoma); BE2-C (neuroblastoma); and SJ-G2 (glioblastoma). Analogues possessing a C
10, C
12 or C
14 alkyl chain or a C
12 linked bis-norcantharimide displayed the highest levels of cytotoxicity.</description><subject>Anticancer</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis</subject><subject>Bridged Bicyclo Compounds, Heterocyclic - chemistry</subject><subject>Bridged Bicyclo Compounds, Heterocyclic - pharmacology</subject><subject>Cantharidin</subject><subject>Cytotoxicity</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General aspects</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>Neoplasms - drug therapy</subject><subject>Neoplasms - pathology</subject><subject>Norcantharidin</subject><subject>Norcantharimides</subject><subject>Pharmacology. Drug treatments</subject><subject>Structure-Activity Relationship</subject><subject>Tumor Cells, Cultured - drug effects</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kU1v1DAQQC0EokvhB3BBucCJpDPxRxJ6QhUflSo4AGfLsSfgVTYpdnbRXvrbmWpXLKceLMvSm6fRsxAvESoENBfrqt_4qgZoKjAVSPVIrFAZVUrZ4WOxgs60JbSdORPPcl4DQK06fCrOsDFgZNOsxN2XOXk3Lb9cipsYKL8t8p6flGMu3BT4LJEBT6lwfom7uOzfFd_-IfNQTPSnmE6WECcecuP8c0sHBaMx_S-inRu3bonz9Fw8GdyY6cXxPhc_Pn74fvW5vPn66frq_U3pZYtLqbxrGgxIjdcata57VAqpVuha6LQKQ6ex7wF0LUl66hyGVmowQTe1b508F28O3ts0_-a9FruJ2dM4uonmbbaGNaarJYN4AH2ac0402FsO49LeItj76HZtObq9j27BWI7OM6-O8m2_oXCaOFZm4PURcNm7cUicIeYTxz_UtrJm7vLAEafYRUo2-0icLMREfrFhjg-s8RdMkKFp</recordid><startdate>20070915</startdate><enddate>20070915</enddate><creator>Hill, Timothy A.</creator><creator>Stewart, Scott G.</creator><creator>Ackland, Stephen P.</creator><creator>Gilbert, Jayne</creator><creator>Sauer, Benjamin</creator><creator>Sakoff, Jennette A.</creator><creator>McCluskey, Adam</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>7X8</scope></search><sort><creationdate>20070915</creationdate><title>Norcantharimides, synthesis and anticancer activity: Synthesis of new norcantharidin analogues and their anticancer evaluation</title><author>Hill, Timothy A. ; Stewart, Scott G. ; Ackland, Stephen P. ; Gilbert, Jayne ; Sauer, Benjamin ; Sakoff, Jennette A. ; McCluskey, Adam</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c381t-4ca771d1e7c551552b1441e241a80954df951bb00523e3ce9a1d83506d572c8a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Anticancer</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis</topic><topic>Bridged Bicyclo Compounds, Heterocyclic - chemistry</topic><topic>Bridged Bicyclo Compounds, Heterocyclic - pharmacology</topic><topic>Cantharidin</topic><topic>Cytotoxicity</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General aspects</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>Neoplasms - drug therapy</topic><topic>Neoplasms - pathology</topic><topic>Norcantharidin</topic><topic>Norcantharimides</topic><topic>Pharmacology. Drug treatments</topic><topic>Structure-Activity Relationship</topic><topic>Tumor Cells, Cultured - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hill, Timothy A.</creatorcontrib><creatorcontrib>Stewart, Scott G.</creatorcontrib><creatorcontrib>Ackland, Stephen P.</creatorcontrib><creatorcontrib>Gilbert, Jayne</creatorcontrib><creatorcontrib>Sauer, Benjamin</creatorcontrib><creatorcontrib>Sakoff, Jennette A.</creatorcontrib><creatorcontrib>McCluskey, Adam</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>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hill, Timothy A.</au><au>Stewart, Scott G.</au><au>Ackland, Stephen P.</au><au>Gilbert, Jayne</au><au>Sauer, Benjamin</au><au>Sakoff, Jennette A.</au><au>McCluskey, Adam</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Norcantharimides, synthesis and anticancer activity: Synthesis of new norcantharidin analogues and their anticancer evaluation</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2007-09-15</date><risdate>2007</risdate><volume>15</volume><issue>18</issue><spage>6126</spage><epage>6134</epage><pages>6126-6134</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A range of amines was reacted with norcantharidin (
2) to provide the corresponding norcantharimides (
9–
43). Treatment of norcantharidin with allylamine afforded the corresponding allyl-norcantharimide (
20) which was amenable to epoxidation (mCPBA,
22) and subsequent ring opening (MeOH/H
+;
23) or alternatively, osmylation (OsO
4/NMO;
24). These simple synthetic modifications of
2 facilitated the development of a novel series of norcantharimides displaying modest to good broad spectrum cytotoxicity against HT29 and SW480 (colorectal carcinoma); MCF-7 (breast adenocarcinoma); A2780 (ovarian carcinoma); H460 (lung carcinoma); A431 (epidermoid carcinoma); DU145 (prostate carcinoma); BE2-C (neuroblastoma); and SJ-G2 (glioblastoma). Analogues possessing a C
10, C
12 or C
14 alkyl chain or a C
12 linked bis-norcantharimide displayed the highest levels of cytotoxicity.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>17606377</pmid><doi>10.1016/j.bmc.2007.06.034</doi><tpages>9</tpages></addata></record> |
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| subjects | Anticancer Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis Bridged Bicyclo Compounds, Heterocyclic - chemistry Bridged Bicyclo Compounds, Heterocyclic - pharmacology Cantharidin Cytotoxicity Drug Screening Assays, Antitumor General aspects Humans Medical sciences Molecular Structure Neoplasms - drug therapy Neoplasms - pathology Norcantharidin Norcantharimides Pharmacology. Drug treatments Structure-Activity Relationship Tumor Cells, Cultured - drug effects |
| title | Norcantharimides, synthesis and anticancer activity: Synthesis of new norcantharidin analogues and their anticancer evaluation |
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