Synthesis of 13-amino costunolide derivatives as anticancer agents
A number of 13-amino costunolide derivatives ( 4a– p) have synthesized and several of them have shown better cytotoxicity with better safety index as compared to costunolide. A number of costunolide derivatives ( 4a– p) have been synthesized and evaluated for their in vitro cytotoxicity against eigh...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2006-08, Vol.16 (16), p.4195-4199 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Srivastava, Sanjay K. Abraham, Aji Bhat, Beena Jaggi, Manu Singh, Anu T. Sanna, Vinod K. Singh, Gurvinder Agarwal, Shiv K. Mukherjee, Rama Burman, Anand C. |
| description | A number of 13-amino costunolide derivatives (
4a–
p) have synthesized and several of them have shown better cytotoxicity with better safety index as compared to costunolide.
A number of costunolide derivatives (
4a–
p) have been synthesized and evaluated for their in vitro cytotoxicity against eight tumor and a non-tumor cell lines. Compound
4d showed around 2-fold better cytotoxicity against SW-620 (colon) cell line with improved safety index than costunolide (
1). While compounds
4e,
4g, and
4p have shown around 2- to 3-fold better cytotoxicity against MIAPaCa2 (pancreas), K-562 (leukemia) and PA-1 (ovary) cell lines as well as better safety index in comparison to costunolide (
1). Compound
4p also exhibited cytotoxicity against HBL100 (breast) cell line with 2-fold better safety index. Structure–activity relationship has been described. |
| doi_str_mv | 10.1016/j.bmcl.2006.05.083 |
| format | Article |
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4a–
p) have synthesized and several of them have shown better cytotoxicity with better safety index as compared to costunolide.
A number of costunolide derivatives (
4a–
p) have been synthesized and evaluated for their in vitro cytotoxicity against eight tumor and a non-tumor cell lines. Compound
4d showed around 2-fold better cytotoxicity against SW-620 (colon) cell line with improved safety index than costunolide (
1). While compounds
4e,
4g, and
4p have shown around 2- to 3-fold better cytotoxicity against MIAPaCa2 (pancreas), K-562 (leukemia) and PA-1 (ovary) cell lines as well as better safety index in comparison to costunolide (
1). Compound
4p also exhibited cytotoxicity against HBL100 (breast) cell line with 2-fold better safety index. Structure–activity relationship has been described.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2006.05.083</identifier><identifier>PMID: 16766184</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Animals ; Anticancer ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Cell Line ; Cell Line, Tumor ; Chemistry, Pharmaceutical - methods ; Costunolide derivatives ; Drug Design ; Drug Screening Assays, Antitumor ; General aspects ; Humans ; K562 Cells ; Medical sciences ; Mice ; Models, Chemical ; Pharmacology. Drug treatments ; Sesquiterpenes - chemical synthesis ; Sesquiterpenes - chemistry</subject><ispartof>Bioorganic & medicinal chemistry letters, 2006-08, Vol.16 (16), p.4195-4199</ispartof><rights>2006 Elsevier Ltd</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c450t-b8a3934bad10f729102208a41439591523971f276b67923109c6a7c2cb41a5193</citedby><cites>FETCH-LOGICAL-c450t-b8a3934bad10f729102208a41439591523971f276b67923109c6a7c2cb41a5193</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X0600638X$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17953136$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16766184$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Srivastava, Sanjay K.</creatorcontrib><creatorcontrib>Abraham, Aji</creatorcontrib><creatorcontrib>Bhat, Beena</creatorcontrib><creatorcontrib>Jaggi, Manu</creatorcontrib><creatorcontrib>Singh, Anu T.</creatorcontrib><creatorcontrib>Sanna, Vinod K.</creatorcontrib><creatorcontrib>Singh, Gurvinder</creatorcontrib><creatorcontrib>Agarwal, Shiv K.</creatorcontrib><creatorcontrib>Mukherjee, Rama</creatorcontrib><creatorcontrib>Burman, Anand C.</creatorcontrib><title>Synthesis of 13-amino costunolide derivatives as anticancer agents</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A number of 13-amino costunolide derivatives (
4a–
p) have synthesized and several of them have shown better cytotoxicity with better safety index as compared to costunolide.
A number of costunolide derivatives (
4a–
p) have been synthesized and evaluated for their in vitro cytotoxicity against eight tumor and a non-tumor cell lines. Compound
4d showed around 2-fold better cytotoxicity against SW-620 (colon) cell line with improved safety index than costunolide (
1). While compounds
4e,
4g, and
4p have shown around 2- to 3-fold better cytotoxicity against MIAPaCa2 (pancreas), K-562 (leukemia) and PA-1 (ovary) cell lines as well as better safety index in comparison to costunolide (
1). Compound
4p also exhibited cytotoxicity against HBL100 (breast) cell line with 2-fold better safety index. Structure–activity relationship has been described.</description><subject>Animals</subject><subject>Anticancer</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Cell Line</subject><subject>Cell Line, Tumor</subject><subject>Chemistry, Pharmaceutical - methods</subject><subject>Costunolide derivatives</subject><subject>Drug Design</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General aspects</subject><subject>Humans</subject><subject>K562 Cells</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Models, Chemical</subject><subject>Pharmacology. Drug treatments</subject><subject>Sesquiterpenes - chemical synthesis</subject><subject>Sesquiterpenes - chemistry</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp90EtLxDAQwPEgiq6PL-BBetFb60xebcCLLr5A8KCCt5CmqWbpQ5Pugt_eLLvgTQjM5T9D-BFyilAgoLxcFHVvu4ICyAJEARXbITPkkueMg9glM1AS8krx9wNyGOMCADlwvk8OUJZSYsVn5OblZ5g-XfQxG9sMWW56P4yZHeO0HMbONy5rXPArM_mVi5lJb5i8NYN1ITMfbpjiMdlrTRfdyXYekbe729f5Q_70fP84v37KLRcw5XVlmGK8Ng1CW1KFQClUhiNnSigUlKkSW1rKWpaKMgRlpSkttTVHI1CxI3KxufsVxu-li5PufbSu68zgxmXUspKclihSSDehDWOMwbX6K_jehB-NoNdyeqHXcnotp0HoJJeWzrbXl3Xvmr-VLVUKzreBidZ0bUgGPv51pRIMmUzd1aZzyWLlXdDRepe8Gh-cnXQz-v_-8QuSmYov</recordid><startdate>20060815</startdate><enddate>20060815</enddate><creator>Srivastava, Sanjay K.</creator><creator>Abraham, Aji</creator><creator>Bhat, Beena</creator><creator>Jaggi, Manu</creator><creator>Singh, Anu T.</creator><creator>Sanna, Vinod K.</creator><creator>Singh, Gurvinder</creator><creator>Agarwal, Shiv K.</creator><creator>Mukherjee, Rama</creator><creator>Burman, Anand C.</creator><general>Elsevier Ltd</general><general>Elsevier</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>20060815</creationdate><title>Synthesis of 13-amino costunolide derivatives as anticancer agents</title><author>Srivastava, Sanjay K. ; Abraham, Aji ; Bhat, Beena ; Jaggi, Manu ; Singh, Anu T. ; Sanna, Vinod K. ; Singh, Gurvinder ; Agarwal, Shiv K. ; Mukherjee, Rama ; Burman, Anand C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c450t-b8a3934bad10f729102208a41439591523971f276b67923109c6a7c2cb41a5193</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Animals</topic><topic>Anticancer</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Cell Line</topic><topic>Cell Line, Tumor</topic><topic>Chemistry, Pharmaceutical - methods</topic><topic>Costunolide derivatives</topic><topic>Drug Design</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General aspects</topic><topic>Humans</topic><topic>K562 Cells</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Models, Chemical</topic><topic>Pharmacology. Drug treatments</topic><topic>Sesquiterpenes - chemical synthesis</topic><topic>Sesquiterpenes - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Srivastava, Sanjay K.</creatorcontrib><creatorcontrib>Abraham, Aji</creatorcontrib><creatorcontrib>Bhat, Beena</creatorcontrib><creatorcontrib>Jaggi, Manu</creatorcontrib><creatorcontrib>Singh, Anu T.</creatorcontrib><creatorcontrib>Sanna, Vinod K.</creatorcontrib><creatorcontrib>Singh, Gurvinder</creatorcontrib><creatorcontrib>Agarwal, Shiv K.</creatorcontrib><creatorcontrib>Mukherjee, Rama</creatorcontrib><creatorcontrib>Burman, Anand C.</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 letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Srivastava, Sanjay K.</au><au>Abraham, Aji</au><au>Bhat, Beena</au><au>Jaggi, Manu</au><au>Singh, Anu T.</au><au>Sanna, Vinod K.</au><au>Singh, Gurvinder</au><au>Agarwal, Shiv K.</au><au>Mukherjee, Rama</au><au>Burman, Anand C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 13-amino costunolide derivatives as anticancer agents</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2006-08-15</date><risdate>2006</risdate><volume>16</volume><issue>16</issue><spage>4195</spage><epage>4199</epage><pages>4195-4199</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A number of 13-amino costunolide derivatives (
4a–
p) have synthesized and several of them have shown better cytotoxicity with better safety index as compared to costunolide.
A number of costunolide derivatives (
4a–
p) have been synthesized and evaluated for their in vitro cytotoxicity against eight tumor and a non-tumor cell lines. Compound
4d showed around 2-fold better cytotoxicity against SW-620 (colon) cell line with improved safety index than costunolide (
1). While compounds
4e,
4g, and
4p have shown around 2- to 3-fold better cytotoxicity against MIAPaCa2 (pancreas), K-562 (leukemia) and PA-1 (ovary) cell lines as well as better safety index in comparison to costunolide (
1). Compound
4p also exhibited cytotoxicity against HBL100 (breast) cell line with 2-fold better safety index. Structure–activity relationship has been described.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16766184</pmid><doi>10.1016/j.bmcl.2006.05.083</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Bioorganic & medicinal chemistry letters, 2006-08, Vol.16 (16), p.4195-4199 |
| issn | 0960-894X 1464-3405 |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Animals Anticancer Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Biological and medical sciences Cell Line Cell Line, Tumor Chemistry, Pharmaceutical - methods Costunolide derivatives Drug Design Drug Screening Assays, Antitumor General aspects Humans K562 Cells Medical sciences Mice Models, Chemical Pharmacology. Drug treatments Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry |
| title | Synthesis of 13-amino costunolide derivatives as anticancer agents |
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