Synthesis and Biological Evaluation of Novel Pyrazolo[4,3-b]oleanane Derivatives as Inhibitors of Glycogen Phosphorylase
Eighteen pyrazolo[4,3‐b]oleanane derivatives have been synthesized and biologically evaluated as inhibitors of rabbit muscle GPa. Key compound 5 was readily obtained in four steps starting from oleanolic acid (OA; 1). Further modification based on pyrazolo triterpene 5 resulted in 17 novel pyrazolo...
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| Veröffentlicht in: | Chemistry & biodiversity 2008-07, Vol.5 (7), p.1304-1312 |
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| creator | Chen, Jun Gong, Yanchun Liu, Jun Hua, Weiyi Zhang, Luyong Sun, Hongbin |
| description | Eighteen pyrazolo[4,3‐b]oleanane derivatives have been synthesized and biologically evaluated as inhibitors of rabbit muscle GPa. Key compound 5 was readily obtained in four steps starting from oleanolic acid (OA; 1). Further modification based on pyrazolo triterpene 5 resulted in 17 novel pyrazolo pentacyclic triterpenes. All of the synthesized pyrazolo[4,3‐b]oleanane derivatives were biologically assayed against rabbit muscle GPa. Within this series of compounds, pyrazole triterpene 19 (IC50=9.9 μM) exhibited more potent activity than the parent compound 1. Preliminary structure–activity relationship analysis of the pyrazolo[4,3‐b]oleanane derivatives as GPa inhibitors is discussed. |
| doi_str_mv | 10.1002/cbdv.200890117 |
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Key compound 5 was readily obtained in four steps starting from oleanolic acid (OA; 1). Further modification based on pyrazolo triterpene 5 resulted in 17 novel pyrazolo pentacyclic triterpenes. All of the synthesized pyrazolo[4,3‐b]oleanane derivatives were biologically assayed against rabbit muscle GPa. Within this series of compounds, pyrazole triterpene 19 (IC50=9.9 μM) exhibited more potent activity than the parent compound 1. Preliminary structure–activity relationship analysis of the pyrazolo[4,3‐b]oleanane derivatives as GPa inhibitors is discussed.</description><identifier>ISSN: 1612-1872</identifier><identifier>EISSN: 1612-1880</identifier><identifier>DOI: 10.1002/cbdv.200890117</identifier><identifier>PMID: 18649317</identifier><language>eng</language><publisher>Zürich: WILEY-VCH Verlag</publisher><subject>3-b]oleanane derivatives ; Animals ; Enzyme Inhibitors - chemical synthesis ; Enzyme Inhibitors - pharmacology ; Glycogen phosphorylase (GPa) ; Glycogen Phosphorylase - antagonists & inhibitors ; Muscles - enzymology ; Oleanolic Acid - analogs & derivatives ; Oleanolic Acid - chemical synthesis ; Oleanolic Acid - pharmacology ; Pyrazoles - chemical synthesis ; Pyrazoles - pharmacology ; Pyrazolo ; Pyrazolo[4,3‐b]oleanane derivatives ; Rabbits ; Structure-Activity Relationship ; Triterpenes</subject><ispartof>Chemistry & biodiversity, 2008-07, Vol.5 (7), p.1304-1312</ispartof><rights>Copyright © 2008 Verlag Helvetica Chimica Acta AG, Zürich</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3817-901a85eaac34bd99e8e294a011a4c7f7f283db534d69885760d9a766cccf14a53</citedby><cites>FETCH-LOGICAL-c3817-901a85eaac34bd99e8e294a011a4c7f7f283db534d69885760d9a766cccf14a53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbdv.200890117$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbdv.200890117$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,778,782,1414,27913,27914,45563,45564</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18649317$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Chen, Jun</creatorcontrib><creatorcontrib>Gong, Yanchun</creatorcontrib><creatorcontrib>Liu, Jun</creatorcontrib><creatorcontrib>Hua, Weiyi</creatorcontrib><creatorcontrib>Zhang, Luyong</creatorcontrib><creatorcontrib>Sun, Hongbin</creatorcontrib><title>Synthesis and Biological Evaluation of Novel Pyrazolo[4,3-b]oleanane Derivatives as Inhibitors of Glycogen Phosphorylase</title><title>Chemistry & biodiversity</title><addtitle>Chemistry & Biodiversity</addtitle><description>Eighteen pyrazolo[4,3‐b]oleanane derivatives have been synthesized and biologically evaluated as inhibitors of rabbit muscle GPa. Key compound 5 was readily obtained in four steps starting from oleanolic acid (OA; 1). Further modification based on pyrazolo triterpene 5 resulted in 17 novel pyrazolo pentacyclic triterpenes. All of the synthesized pyrazolo[4,3‐b]oleanane derivatives were biologically assayed against rabbit muscle GPa. Within this series of compounds, pyrazole triterpene 19 (IC50=9.9 μM) exhibited more potent activity than the parent compound 1. Preliminary structure–activity relationship analysis of the pyrazolo[4,3‐b]oleanane derivatives as GPa inhibitors is discussed.</description><subject>3-b]oleanane derivatives</subject><subject>Animals</subject><subject>Enzyme Inhibitors - chemical synthesis</subject><subject>Enzyme Inhibitors - pharmacology</subject><subject>Glycogen phosphorylase (GPa)</subject><subject>Glycogen Phosphorylase - antagonists & inhibitors</subject><subject>Muscles - enzymology</subject><subject>Oleanolic Acid - analogs & derivatives</subject><subject>Oleanolic Acid - chemical synthesis</subject><subject>Oleanolic Acid - pharmacology</subject><subject>Pyrazoles - chemical synthesis</subject><subject>Pyrazoles - pharmacology</subject><subject>Pyrazolo</subject><subject>Pyrazolo[4,3‐b]oleanane derivatives</subject><subject>Rabbits</subject><subject>Structure-Activity Relationship</subject><subject>Triterpenes</subject><issn>1612-1872</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM9v0zAYhq0JtI3BlSPKidNS7DjxjyPrRpmYxqSOgYSQ9cVxVoMbFzsNy_56XLUqu3HyJ-t5H33fi9BrgicE4-KdrpthUmAsJCaEH6BjwkiREyHws_3MiyP0IsafiU__4hAdEcFKSQk_Rg_zsesXJtqYQddkZ9Y7f281uOxiALeG3vou82127QfjspsxwGMivpenNK9_eGegg85k5ybYIbGDSZqYXXYLW9veh7iJztyo_b3pspuFj6uFD6ODaF6i5y24aF7t3hP05cPF7fRjfvV5djl9f5VrKgjP01kgKgOgaVk3UhphCllCOhZKzVveFoI2dUXLhkkhKs5wI4EzprVuSQkVPUFvt95V8L_XJvZqaaM2zqW9_ToqJmnFOKMJnGxBHXyMwbRqFewSwqgIVpuu1aZrte86Bd7szOt6aZp_-K7cBMgt8Mc6M_5Hp6Zn53dP5fk2a2NvHvZZCL8U45RX6uv1TN1V8-LTLZmrb_Qvii6cYA</recordid><startdate>200807</startdate><enddate>200807</enddate><creator>Chen, Jun</creator><creator>Gong, Yanchun</creator><creator>Liu, Jun</creator><creator>Hua, Weiyi</creator><creator>Zhang, Luyong</creator><creator>Sun, Hongbin</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</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>200807</creationdate><title>Synthesis and Biological Evaluation of Novel Pyrazolo[4,3-b]oleanane Derivatives as Inhibitors of Glycogen Phosphorylase</title><author>Chen, Jun ; Gong, Yanchun ; Liu, Jun ; Hua, Weiyi ; Zhang, Luyong ; Sun, Hongbin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3817-901a85eaac34bd99e8e294a011a4c7f7f283db534d69885760d9a766cccf14a53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>3-b]oleanane derivatives</topic><topic>Animals</topic><topic>Enzyme Inhibitors - chemical synthesis</topic><topic>Enzyme Inhibitors - pharmacology</topic><topic>Glycogen phosphorylase (GPa)</topic><topic>Glycogen Phosphorylase - antagonists & inhibitors</topic><topic>Muscles - enzymology</topic><topic>Oleanolic Acid - analogs & derivatives</topic><topic>Oleanolic Acid - chemical synthesis</topic><topic>Oleanolic Acid - pharmacology</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - pharmacology</topic><topic>Pyrazolo</topic><topic>Pyrazolo[4,3‐b]oleanane derivatives</topic><topic>Rabbits</topic><topic>Structure-Activity Relationship</topic><topic>Triterpenes</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chen, Jun</creatorcontrib><creatorcontrib>Gong, Yanchun</creatorcontrib><creatorcontrib>Liu, Jun</creatorcontrib><creatorcontrib>Hua, Weiyi</creatorcontrib><creatorcontrib>Zhang, Luyong</creatorcontrib><creatorcontrib>Sun, Hongbin</creatorcontrib><collection>Istex</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>Chemistry & biodiversity</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chen, Jun</au><au>Gong, Yanchun</au><au>Liu, Jun</au><au>Hua, Weiyi</au><au>Zhang, Luyong</au><au>Sun, Hongbin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Biological Evaluation of Novel Pyrazolo[4,3-b]oleanane Derivatives as Inhibitors of Glycogen Phosphorylase</atitle><jtitle>Chemistry & biodiversity</jtitle><addtitle>Chemistry & Biodiversity</addtitle><date>2008-07</date><risdate>2008</risdate><volume>5</volume><issue>7</issue><spage>1304</spage><epage>1312</epage><pages>1304-1312</pages><issn>1612-1872</issn><eissn>1612-1880</eissn><abstract>Eighteen pyrazolo[4,3‐b]oleanane derivatives have been synthesized and biologically evaluated as inhibitors of rabbit muscle GPa. Key compound 5 was readily obtained in four steps starting from oleanolic acid (OA; 1). Further modification based on pyrazolo triterpene 5 resulted in 17 novel pyrazolo pentacyclic triterpenes. All of the synthesized pyrazolo[4,3‐b]oleanane derivatives were biologically assayed against rabbit muscle GPa. Within this series of compounds, pyrazole triterpene 19 (IC50=9.9 μM) exhibited more potent activity than the parent compound 1. Preliminary structure–activity relationship analysis of the pyrazolo[4,3‐b]oleanane derivatives as GPa inhibitors is discussed.</abstract><cop>Zürich</cop><pub>WILEY-VCH Verlag</pub><pmid>18649317</pmid><doi>10.1002/cbdv.200890117</doi><tpages>9</tpages></addata></record> |
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| subjects | 3-b]oleanane derivatives Animals Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - pharmacology Glycogen phosphorylase (GPa) Glycogen Phosphorylase - antagonists & inhibitors Muscles - enzymology Oleanolic Acid - analogs & derivatives Oleanolic Acid - chemical synthesis Oleanolic Acid - pharmacology Pyrazoles - chemical synthesis Pyrazoles - pharmacology Pyrazolo Pyrazolo[4,3‐b]oleanane derivatives Rabbits Structure-Activity Relationship Triterpenes |
| title | Synthesis and Biological Evaluation of Novel Pyrazolo[4,3-b]oleanane Derivatives as Inhibitors of Glycogen Phosphorylase |
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