Syntheses of 1,2,3-triazolyl salicylamides with inhibitory activity on lipopolysaccharide-induced nitric oxide production
A 28-membered 1,2,3-triazolyl salicylamide library was synthesized via a click chemistry. Compound 29g inhibited NO production in LPS-activated RAW264.7 macrophage cells with the IC 50 value of 12.8 μM. A 28-membered 1,2,3-triazolyl salicylamide library was synthesized via a Cu(I)-catalyzed azide-al...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2011-04, Vol.21 (7), p.1953-1957 |
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| container_end_page | 1957 |
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| container_issue | 7 |
| container_start_page | 1953 |
| container_title | Bioorganic & medicinal chemistry letters |
| container_volume | 21 |
| creator | Yoon, Jieun Cho, Lan Lee, Sang Kook Ryu, Jae-Sang |
| description | A 28-membered 1,2,3-triazolyl salicylamide library was synthesized via a click chemistry. Compound
29g inhibited NO production in LPS-activated RAW264.7 macrophage cells with the IC
50 value of 12.8
μM.
A 28-membered 1,2,3-triazolyl salicylamide library was synthesized via a Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition and evaluated for their abilities to inhibit NO production in LPS-activated RAW264.7 macrophage cells. Among 28 analogues,
29g showed a significant inhibitory activity (IC
50
=
12.8
μM). The inhibitory effects of
29g on LPS-mediated NO production in macrophage cells appeared to be associated with the suppression of iNOS expression. |
| doi_str_mv | 10.1016/j.bmcl.2011.02.034 |
| format | Article |
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29g inhibited NO production in LPS-activated RAW264.7 macrophage cells with the IC
50 value of 12.8
μM.
A 28-membered 1,2,3-triazolyl salicylamide library was synthesized via a Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition and evaluated for their abilities to inhibit NO production in LPS-activated RAW264.7 macrophage cells. Among 28 analogues,
29g showed a significant inhibitory activity (IC
50
=
12.8
μM). The inhibitory effects of
29g on LPS-mediated NO production in macrophage cells appeared to be associated with the suppression of iNOS expression.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2011.02.034</identifier><identifier>PMID: 21377876</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Animals ; Biological and medical sciences ; Bones, joints and connective tissue. Antiinflammatory agents ; Cell Line ; Click chemistry ; copper ; inducible nitric oxide synthase ; Inhibitory Concentration 50 ; iNOS ; Library ; Lipopolysaccharides - pharmacology ; macrophages ; Medical sciences ; Mice ; nitric oxide ; Nitric Oxide - antagonists & inhibitors ; Nitric Oxide - biosynthesis ; Nitric Oxide Synthase Type II - antagonists & inhibitors ; Nitric Oxide Synthase Type II - metabolism ; Pharmacology. Drug treatments ; Salicylamide ; Salicylamides - chemical synthesis ; Salicylamides - pharmacology ; Triazole</subject><ispartof>Bioorganic & medicinal chemistry letters, 2011-04, Vol.21 (7), p.1953-1957</ispartof><rights>2011 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c441t-2c8176dc448f28513b0f1b4fb388585bc1aa31376cf7eb4161739aeb2cd70abb3</citedby><cites>FETCH-LOGICAL-c441t-2c8176dc448f28513b0f1b4fb388585bc1aa31376cf7eb4161739aeb2cd70abb3</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.2011.02.034$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,778,782,3539,27907,27908,45978</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23982113$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21377876$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Yoon, Jieun</creatorcontrib><creatorcontrib>Cho, Lan</creatorcontrib><creatorcontrib>Lee, Sang Kook</creatorcontrib><creatorcontrib>Ryu, Jae-Sang</creatorcontrib><title>Syntheses of 1,2,3-triazolyl salicylamides with inhibitory activity on lipopolysaccharide-induced nitric oxide production</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A 28-membered 1,2,3-triazolyl salicylamide library was synthesized via a click chemistry. Compound
29g inhibited NO production in LPS-activated RAW264.7 macrophage cells with the IC
50 value of 12.8
μM.
A 28-membered 1,2,3-triazolyl salicylamide library was synthesized via a Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition and evaluated for their abilities to inhibit NO production in LPS-activated RAW264.7 macrophage cells. Among 28 analogues,
29g showed a significant inhibitory activity (IC
50
=
12.8
μM). The inhibitory effects of
29g on LPS-mediated NO production in macrophage cells appeared to be associated with the suppression of iNOS expression.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>Cell Line</subject><subject>Click chemistry</subject><subject>copper</subject><subject>inducible nitric oxide synthase</subject><subject>Inhibitory Concentration 50</subject><subject>iNOS</subject><subject>Library</subject><subject>Lipopolysaccharides - pharmacology</subject><subject>macrophages</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>nitric oxide</subject><subject>Nitric Oxide - antagonists & inhibitors</subject><subject>Nitric Oxide - biosynthesis</subject><subject>Nitric Oxide Synthase Type II - antagonists & inhibitors</subject><subject>Nitric Oxide Synthase Type II - metabolism</subject><subject>Pharmacology. Drug treatments</subject><subject>Salicylamide</subject><subject>Salicylamides - chemical synthesis</subject><subject>Salicylamides - pharmacology</subject><subject>Triazole</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU2PFCEQhonRuLOrf8CDcjF72W4poBsm8WI2fiWbeFg38UaAph0mdDMCs9r-epnMqDc9ESrPWwX1IPQMSAsE-lfb1kw2tJQAtIS2hPEHaAW85w3jpHuIVmTdk0au-ZczdJ7zlhDghPPH6IwCE0KKfoWW22UuG5ddxnHEcEWvWFOS1z9jWALOOni7BD35oQLffdlgP2-88SWmBWtb_L0vC44zDn4XdzWTtbUbnSrf-HnYWzfg2deGFscftYh3KdZq8XF-gh6NOmT39HReoLt3bz9ff2huPr3_eP3mprGcQ2molSD6oV7kSGUHzJARDB8Nk7KTnbGgNavf6e0onOHQg2Br7Qy1gyDaGHaBLo996-hve5eLmny2LgQ9u7jPSvZUSLrm4v9kJ4DVzR9IeiRtijknN6pd8pNOiwKiDm7UVh3cqIMbRaiqbmro-an93kxu-BP5LaMCL0-AzlaHMenZ-vyXY2tJAVjlXhy5UUelv6bK3N3WSV0VzHgPshKvj4Sri733LqlsvZurDZ-cLWqI_l8v_QUP_bgj</recordid><startdate>20110401</startdate><enddate>20110401</enddate><creator>Yoon, Jieun</creator><creator>Cho, Lan</creator><creator>Lee, Sang Kook</creator><creator>Ryu, Jae-Sang</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20110401</creationdate><title>Syntheses of 1,2,3-triazolyl salicylamides with inhibitory activity on lipopolysaccharide-induced nitric oxide production</title><author>Yoon, Jieun ; Cho, Lan ; Lee, Sang Kook ; Ryu, Jae-Sang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c441t-2c8176dc448f28513b0f1b4fb388585bc1aa31376cf7eb4161739aeb2cd70abb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>Cell Line</topic><topic>Click chemistry</topic><topic>copper</topic><topic>inducible nitric oxide synthase</topic><topic>Inhibitory Concentration 50</topic><topic>iNOS</topic><topic>Library</topic><topic>Lipopolysaccharides - pharmacology</topic><topic>macrophages</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>nitric oxide</topic><topic>Nitric Oxide - antagonists & inhibitors</topic><topic>Nitric Oxide - biosynthesis</topic><topic>Nitric Oxide Synthase Type II - antagonists & inhibitors</topic><topic>Nitric Oxide Synthase Type II - metabolism</topic><topic>Pharmacology. Drug treatments</topic><topic>Salicylamide</topic><topic>Salicylamides - chemical synthesis</topic><topic>Salicylamides - pharmacology</topic><topic>Triazole</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yoon, Jieun</creatorcontrib><creatorcontrib>Cho, Lan</creatorcontrib><creatorcontrib>Lee, Sang Kook</creatorcontrib><creatorcontrib>Ryu, Jae-Sang</creatorcontrib><collection>AGRIS</collection><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><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 letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yoon, Jieun</au><au>Cho, Lan</au><au>Lee, Sang Kook</au><au>Ryu, Jae-Sang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Syntheses of 1,2,3-triazolyl salicylamides with inhibitory activity on lipopolysaccharide-induced nitric oxide production</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2011-04-01</date><risdate>2011</risdate><volume>21</volume><issue>7</issue><spage>1953</spage><epage>1957</epage><pages>1953-1957</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A 28-membered 1,2,3-triazolyl salicylamide library was synthesized via a click chemistry. Compound
29g inhibited NO production in LPS-activated RAW264.7 macrophage cells with the IC
50 value of 12.8
μM.
A 28-membered 1,2,3-triazolyl salicylamide library was synthesized via a Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition and evaluated for their abilities to inhibit NO production in LPS-activated RAW264.7 macrophage cells. Among 28 analogues,
29g showed a significant inhibitory activity (IC
50
=
12.8
μM). The inhibitory effects of
29g on LPS-mediated NO production in macrophage cells appeared to be associated with the suppression of iNOS expression.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>21377876</pmid><doi>10.1016/j.bmcl.2011.02.034</doi><tpages>5</tpages></addata></record> |
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| source | Elsevier ScienceDirect Journals Complete - AutoHoldings; MEDLINE |
| subjects | Animals Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents Cell Line Click chemistry copper inducible nitric oxide synthase Inhibitory Concentration 50 iNOS Library Lipopolysaccharides - pharmacology macrophages Medical sciences Mice nitric oxide Nitric Oxide - antagonists & inhibitors Nitric Oxide - biosynthesis Nitric Oxide Synthase Type II - antagonists & inhibitors Nitric Oxide Synthase Type II - metabolism Pharmacology. Drug treatments Salicylamide Salicylamides - chemical synthesis Salicylamides - pharmacology Triazole |
| title | Syntheses of 1,2,3-triazolyl salicylamides with inhibitory activity on lipopolysaccharide-induced nitric oxide production |
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