Synthesis, in vitro inhibitory activity towards COX-2 and haemolytic activity of derivatives of Esculentoside A
Twenty-one derivatives of Esculentoside A were synthesized. The conversion of the carboxylic acid into amides can highly enhance their inhibitory activity towards COX-2, and also increased the haemolytic activity. Esculentoside A (EsA) has been reported to possess anti-inflammatory activity and sele...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2007-12, Vol.17 (23), p.6430-6433 |
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| creator | Wu, Fei Yi, Yanghua Sun, Peng Zhang, Dazhi |
| description | Twenty-one derivatives of Esculentoside A were synthesized. The conversion of the carboxylic acid into amides can highly enhance their inhibitory activity towards COX-2, and also increased the haemolytic activity.
Esculentoside A (EsA) has been reported to possess anti-inflammatory activity and selective inhibitory activity towards cyclooxygenase-2. A series of derivatives of EsA were synthesized by converting the C-28 carboxylic acid group into amides. The haemolytic activity and inhibitory activity towards cyclooxygenase-2 were evaluated in vitro. The SAR study of the derivatives was conducted and showed that introducing aromatic ring to EsA greatly enhanced its biological activity. Compound
23 showed higher inhibitory activity than Celecoxib and EsA, but lower haemolytic toxicity than EsA. |
| doi_str_mv | 10.1016/j.bmcl.2007.10.006 |
| format | Article |
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Esculentoside A (EsA) has been reported to possess anti-inflammatory activity and selective inhibitory activity towards cyclooxygenase-2. A series of derivatives of EsA were synthesized by converting the C-28 carboxylic acid group into amides. The haemolytic activity and inhibitory activity towards cyclooxygenase-2 were evaluated in vitro. The SAR study of the derivatives was conducted and showed that introducing aromatic ring to EsA greatly enhanced its biological activity. Compound
23 showed higher inhibitory activity than Celecoxib and EsA, but lower haemolytic toxicity than EsA.</description><identifier>ISSN: 0960-894X</identifier><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3405</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmcl.2007.10.006</identifier><identifier>PMID: 17950600</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Animals ; Anti-inflammatory ; Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis ; Anti-Inflammatory Agents, Non-Steroidal - pharmacology ; Biological and medical sciences ; Bones, joints and connective tissue. Antiinflammatory agents ; Cell Line ; Cyclooxygenase 2 - biosynthesis ; Cyclooxygenase 2 - metabolism ; Cyclooxygenase 2 Inhibitors - chemical synthesis ; Cyclooxygenase 2 Inhibitors - pharmacology ; Derivatives ; Esculentoside A ; Hemolysis - drug effects ; Hemolysis - physiology ; Humans ; Insecta ; Medical sciences ; Oleanolic Acid - analogs & derivatives ; Oleanolic Acid - chemical synthesis ; Oleanolic Acid - pharmacology ; Pharmacology. Drug treatments ; Rabbits ; Saponins - chemical synthesis ; Saponins - pharmacology ; Structure-Activity Relationship ; Synthesis</subject><ispartof>Bioorganic & medicinal chemistry, 2007-12, Vol.17 (23), p.6430-6433</ispartof><rights>2007 Elsevier Ltd</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-7349b3894b047afe388150025e000b360436f413d0f9bd5f9ec9826ed0bf214d3</citedby><cites>FETCH-LOGICAL-c415t-7349b3894b047afe388150025e000b360436f413d0f9bd5f9ec9826ed0bf214d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X07011754$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=19372311$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17950600$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wu, Fei</creatorcontrib><creatorcontrib>Yi, Yanghua</creatorcontrib><creatorcontrib>Sun, Peng</creatorcontrib><creatorcontrib>Zhang, Dazhi</creatorcontrib><title>Synthesis, in vitro inhibitory activity towards COX-2 and haemolytic activity of derivatives of Esculentoside A</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Twenty-one derivatives of Esculentoside A were synthesized. The conversion of the carboxylic acid into amides can highly enhance their inhibitory activity towards COX-2, and also increased the haemolytic activity.
Esculentoside A (EsA) has been reported to possess anti-inflammatory activity and selective inhibitory activity towards cyclooxygenase-2. A series of derivatives of EsA were synthesized by converting the C-28 carboxylic acid group into amides. The haemolytic activity and inhibitory activity towards cyclooxygenase-2 were evaluated in vitro. The SAR study of the derivatives was conducted and showed that introducing aromatic ring to EsA greatly enhanced its biological activity. Compound
23 showed higher inhibitory activity than Celecoxib and EsA, but lower haemolytic toxicity than EsA.</description><subject>Animals</subject><subject>Anti-inflammatory</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>Cell Line</subject><subject>Cyclooxygenase 2 - biosynthesis</subject><subject>Cyclooxygenase 2 - metabolism</subject><subject>Cyclooxygenase 2 Inhibitors - chemical synthesis</subject><subject>Cyclooxygenase 2 Inhibitors - pharmacology</subject><subject>Derivatives</subject><subject>Esculentoside A</subject><subject>Hemolysis - drug effects</subject><subject>Hemolysis - physiology</subject><subject>Humans</subject><subject>Insecta</subject><subject>Medical sciences</subject><subject>Oleanolic Acid - analogs & derivatives</subject><subject>Oleanolic Acid - chemical synthesis</subject><subject>Oleanolic Acid - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Rabbits</subject><subject>Saponins - chemical synthesis</subject><subject>Saponins - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Synthesis</subject><issn>0960-894X</issn><issn>0968-0896</issn><issn>1464-3405</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEtr3DAURkVpaSZp_kAXxZt2FU-vLPkh6CYMSVsIZNEWshOydMVosK1U0kzxv4-cGZhdV9L9OPfBIeQjhTUF2nzdrftRD-sKoM3BGqB5Q1aUN7xkHOq3ZAWigbIT_OmCXMa4A6AcOH9PLmgramgAVsT_mqe0xejiTeGm4uBS8Pmzdb1LPsyF0snlcC6S_6eCicXm8amsCjWZYqtw9MOcnD5T3hYGgzuoXGNcyruo9wNOyUdnsLj9QN5ZNUS8Pr1X5M_93e_Nj_Lh8fvPze1DqTmtU9kyLnqWT--Bt8oi6zpaA1Q1AkDPGuCssZwyA1b0prYCteiqBg30tqLcsCvy5Tj3Ofi_e4xJji5qHAY1od9HSQVrOk5pBqsjqIOPMaCVz8GNKsySglw0y51cNMtF85Jlzbnp02n6vh_RnFtOXjPw-QSoqNVgg5q0i2dOsLZir9u_HTnMLg4Og4za4aTRuIA6SePd_-54AbRhm6s</recordid><startdate>20071201</startdate><enddate>20071201</enddate><creator>Wu, Fei</creator><creator>Yi, Yanghua</creator><creator>Sun, Peng</creator><creator>Zhang, Dazhi</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20071201</creationdate><title>Synthesis, in vitro inhibitory activity towards COX-2 and haemolytic activity of derivatives of Esculentoside A</title><author>Wu, Fei ; Yi, Yanghua ; Sun, Peng ; Zhang, Dazhi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-7349b3894b047afe388150025e000b360436f413d0f9bd5f9ec9826ed0bf214d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Animals</topic><topic>Anti-inflammatory</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>Cell Line</topic><topic>Cyclooxygenase 2 - biosynthesis</topic><topic>Cyclooxygenase 2 - metabolism</topic><topic>Cyclooxygenase 2 Inhibitors - chemical synthesis</topic><topic>Cyclooxygenase 2 Inhibitors - pharmacology</topic><topic>Derivatives</topic><topic>Esculentoside A</topic><topic>Hemolysis - drug effects</topic><topic>Hemolysis - physiology</topic><topic>Humans</topic><topic>Insecta</topic><topic>Medical sciences</topic><topic>Oleanolic Acid - analogs & derivatives</topic><topic>Oleanolic Acid - chemical synthesis</topic><topic>Oleanolic Acid - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Rabbits</topic><topic>Saponins - chemical synthesis</topic><topic>Saponins - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wu, Fei</creatorcontrib><creatorcontrib>Yi, Yanghua</creatorcontrib><creatorcontrib>Sun, Peng</creatorcontrib><creatorcontrib>Zhang, Dazhi</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>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wu, Fei</au><au>Yi, Yanghua</au><au>Sun, Peng</au><au>Zhang, Dazhi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, in vitro inhibitory activity towards COX-2 and haemolytic activity of derivatives of Esculentoside A</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2007-12-01</date><risdate>2007</risdate><volume>17</volume><issue>23</issue><spage>6430</spage><epage>6433</epage><pages>6430-6433</pages><issn>0960-894X</issn><issn>0968-0896</issn><eissn>1464-3405</eissn><eissn>1464-3391</eissn><abstract>Twenty-one derivatives of Esculentoside A were synthesized. The conversion of the carboxylic acid into amides can highly enhance their inhibitory activity towards COX-2, and also increased the haemolytic activity.
Esculentoside A (EsA) has been reported to possess anti-inflammatory activity and selective inhibitory activity towards cyclooxygenase-2. A series of derivatives of EsA were synthesized by converting the C-28 carboxylic acid group into amides. The haemolytic activity and inhibitory activity towards cyclooxygenase-2 were evaluated in vitro. The SAR study of the derivatives was conducted and showed that introducing aromatic ring to EsA greatly enhanced its biological activity. Compound
23 showed higher inhibitory activity than Celecoxib and EsA, but lower haemolytic toxicity than EsA.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>17950600</pmid><doi>10.1016/j.bmcl.2007.10.006</doi><tpages>4</tpages></addata></record> |
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| subjects | Animals Anti-inflammatory Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis Anti-Inflammatory Agents, Non-Steroidal - pharmacology Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents Cell Line Cyclooxygenase 2 - biosynthesis Cyclooxygenase 2 - metabolism Cyclooxygenase 2 Inhibitors - chemical synthesis Cyclooxygenase 2 Inhibitors - pharmacology Derivatives Esculentoside A Hemolysis - drug effects Hemolysis - physiology Humans Insecta Medical sciences Oleanolic Acid - analogs & derivatives Oleanolic Acid - chemical synthesis Oleanolic Acid - pharmacology Pharmacology. Drug treatments Rabbits Saponins - chemical synthesis Saponins - pharmacology Structure-Activity Relationship Synthesis |
| title | Synthesis, in vitro inhibitory activity towards COX-2 and haemolytic activity of derivatives of Esculentoside A |
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