Synthesis and preliminary biological evaluation of truncated zoanthenol analogues
Graphic Zoanthamines are a family of marine alkaloids that have complex heptacyclic structures and are reported to be interleukin-6 modulators. While the structure of zoanthamines, especially the ABC-ring portion, is similar to that of steroids, the CDEFG-ring portion, composed of aminoacetal and la...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2004-05, Vol.14 (10), p.2647-2651 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Hirai, Go Oguri, Hiroki Hayashi, Masahiko Koyama, Koji Koizumi, Yuuki Moharram, Sameh M. Hirama, Masahiro |
| description | Graphic
Zoanthamines are a family of marine alkaloids that have complex heptacyclic structures and are reported to be interleukin-6 modulators. While the structure of zoanthamines, especially the ABC-ring portion, is similar to that of steroids, the CDEFG-ring portion, composed of aminoacetal and lactone core, is a unique structural element. In this report, we designed and synthesized ABC-ring
6 and CDEFG-ring
7, which are truncated analogues of the northern and southern hemispheres of zoanthenol
5, respectively, and which incorporate all of the functionality of each hemisphere. A preliminary SAR study suggested that the hydrochloride of the CEFG-ring portion is an active pharmacophore for suppressing the growth of interleukin-6-dependent MH60 cells. |
| doi_str_mv | 10.1016/j.bmcl.2004.02.064 |
| format | Article |
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Zoanthamines are a family of marine alkaloids that have complex heptacyclic structures and are reported to be interleukin-6 modulators. While the structure of zoanthamines, especially the ABC-ring portion, is similar to that of steroids, the CDEFG-ring portion, composed of aminoacetal and lactone core, is a unique structural element. In this report, we designed and synthesized ABC-ring
6 and CDEFG-ring
7, which are truncated analogues of the northern and southern hemispheres of zoanthenol
5, respectively, and which incorporate all of the functionality of each hemisphere. A preliminary SAR study suggested that the hydrochloride of the CEFG-ring portion is an active pharmacophore for suppressing the growth of interleukin-6-dependent MH60 cells.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2004.02.064</identifier><identifier>PMID: 15109670</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Alkaloids - chemical synthesis ; Alkaloids - pharmacology ; Animals ; Biological and medical sciences ; Bones, joints and connective tissue. Antiinflammatory agents ; Cell Proliferation - drug effects ; Cnidaria - chemistry ; Dose-Response Relationship, Drug ; Drug Design ; Heterocyclic Compounds, Bridged-Ring - chemical synthesis ; Heterocyclic Compounds, Bridged-Ring - pharmacology ; Hybridomas ; Interleukin-6 - antagonists & inhibitors ; Medical sciences ; Mice ; Molecular Mimicry ; Osteoporosis - drug therapy ; Pharmacology. Drug treatments ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2004-05, Vol.14 (10), p.2647-2651</ispartof><rights>2004 Elsevier Ltd</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c382t-4566af072f8ddd6cdec08cc8a2286f8e19d132d5b4d621f3abed9e0367178ff03</citedby><cites>FETCH-LOGICAL-c382t-4566af072f8ddd6cdec08cc8a2286f8e19d132d5b4d621f3abed9e0367178ff03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2004.02.064$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15707804$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15109670$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hirai, Go</creatorcontrib><creatorcontrib>Oguri, Hiroki</creatorcontrib><creatorcontrib>Hayashi, Masahiko</creatorcontrib><creatorcontrib>Koyama, Koji</creatorcontrib><creatorcontrib>Koizumi, Yuuki</creatorcontrib><creatorcontrib>Moharram, Sameh M.</creatorcontrib><creatorcontrib>Hirama, Masahiro</creatorcontrib><title>Synthesis and preliminary biological evaluation of truncated zoanthenol analogues</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Graphic
Zoanthamines are a family of marine alkaloids that have complex heptacyclic structures and are reported to be interleukin-6 modulators. While the structure of zoanthamines, especially the ABC-ring portion, is similar to that of steroids, the CDEFG-ring portion, composed of aminoacetal and lactone core, is a unique structural element. In this report, we designed and synthesized ABC-ring
6 and CDEFG-ring
7, which are truncated analogues of the northern and southern hemispheres of zoanthenol
5, respectively, and which incorporate all of the functionality of each hemisphere. A preliminary SAR study suggested that the hydrochloride of the CEFG-ring portion is an active pharmacophore for suppressing the growth of interleukin-6-dependent MH60 cells.</description><subject>Alkaloids - chemical synthesis</subject><subject>Alkaloids - pharmacology</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>Cell Proliferation - drug effects</subject><subject>Cnidaria - chemistry</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Design</subject><subject>Heterocyclic Compounds, Bridged-Ring - chemical synthesis</subject><subject>Heterocyclic Compounds, Bridged-Ring - pharmacology</subject><subject>Hybridomas</subject><subject>Interleukin-6 - antagonists & inhibitors</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Molecular Mimicry</subject><subject>Osteoporosis - drug therapy</subject><subject>Pharmacology. 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Antiinflammatory agents</topic><topic>Cell Proliferation - drug effects</topic><topic>Cnidaria - chemistry</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Design</topic><topic>Heterocyclic Compounds, Bridged-Ring - chemical synthesis</topic><topic>Heterocyclic Compounds, Bridged-Ring - pharmacology</topic><topic>Hybridomas</topic><topic>Interleukin-6 - antagonists & inhibitors</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Molecular Mimicry</topic><topic>Osteoporosis - drug therapy</topic><topic>Pharmacology. Drug treatments</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hirai, Go</creatorcontrib><creatorcontrib>Oguri, Hiroki</creatorcontrib><creatorcontrib>Hayashi, Masahiko</creatorcontrib><creatorcontrib>Koyama, Koji</creatorcontrib><creatorcontrib>Koizumi, Yuuki</creatorcontrib><creatorcontrib>Moharram, Sameh M.</creatorcontrib><creatorcontrib>Hirama, Masahiro</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>Hirai, Go</au><au>Oguri, Hiroki</au><au>Hayashi, Masahiko</au><au>Koyama, Koji</au><au>Koizumi, Yuuki</au><au>Moharram, Sameh M.</au><au>Hirama, Masahiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and preliminary biological evaluation of truncated zoanthenol analogues</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2004-05-17</date><risdate>2004</risdate><volume>14</volume><issue>10</issue><spage>2647</spage><epage>2651</epage><pages>2647-2651</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Graphic
Zoanthamines are a family of marine alkaloids that have complex heptacyclic structures and are reported to be interleukin-6 modulators. While the structure of zoanthamines, especially the ABC-ring portion, is similar to that of steroids, the CDEFG-ring portion, composed of aminoacetal and lactone core, is a unique structural element. In this report, we designed and synthesized ABC-ring
6 and CDEFG-ring
7, which are truncated analogues of the northern and southern hemispheres of zoanthenol
5, respectively, and which incorporate all of the functionality of each hemisphere. A preliminary SAR study suggested that the hydrochloride of the CEFG-ring portion is an active pharmacophore for suppressing the growth of interleukin-6-dependent MH60 cells.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>15109670</pmid><doi>10.1016/j.bmcl.2004.02.064</doi><tpages>5</tpages></addata></record> |
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| subjects | Alkaloids - chemical synthesis Alkaloids - pharmacology Animals Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents Cell Proliferation - drug effects Cnidaria - chemistry Dose-Response Relationship, Drug Drug Design Heterocyclic Compounds, Bridged-Ring - chemical synthesis Heterocyclic Compounds, Bridged-Ring - pharmacology Hybridomas Interleukin-6 - antagonists & inhibitors Medical sciences Mice Molecular Mimicry Osteoporosis - drug therapy Pharmacology. Drug treatments Structure-Activity Relationship |
| title | Synthesis and preliminary biological evaluation of truncated zoanthenol analogues |
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