Synthesis and Evaluation of Anti‐inflammatory N‐Substituted 3,5‐Bis(2‐(trifluoromethyl)benzylidene)piperidin‐4‐ones
A total of 24 N‐substituted 3,5‐bis(2‐(trifluoromethyl)benzylidene)piperidin‐4‐one derivatives were synthesized via aldol condensation, and their anti‐inflammatory activities were evaluated. These compounds were found to have no significant cytotoxicity against mouse bone marrow cells in vitro. Howe...
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| creator | Xie, Zixin Zhang, Zaikui Yu, Shufang Cheng, Donghua Zhang, Huan Han, Chao Lv, Handeng Ye, Faqing |
| description | A total of 24 N‐substituted 3,5‐bis(2‐(trifluoromethyl)benzylidene)piperidin‐4‐one derivatives were synthesized via aldol condensation, and their anti‐inflammatory activities were evaluated. These compounds were found to have no significant cytotoxicity against mouse bone marrow cells in vitro. However, some compounds, such as c6 (N‐(3‐methylbenzoyl)‐3,5‐bis‐(2‐(trifluoromethyl)benzylidene)piperidin‐4‐one) and c10 (N‐(2‐chlorobenzoyl)‐3,5‐bis‐(2‐(trifluoromethyl)benzylidene)piperidin‐4‐one), displayed potent anti‐inflammatory activity by inhibiting lipopolysaccharide (LPS)‐stimulated tumor necrosis factor (TNF)‐α, interleukin‐6 (IL‐6), IL‐1β, prostaglandin E2 (PGE2), and nitric oxide (NO) production in RAW 264.7 cells. Treatment with c6 or c10 at 2.5 or 10 mg kg−1 significantly decreased the paw edema induced by carrageenan in rats, and the anti‐inflammatory effects of these compounds were found to be better than those of celecoxib or indomethacin as well as their parent compound C66 (2,6‐bis‐(2‐(trifluoromethyl)benzylidene)cyclohexanone). Pharmacokinetic analysis indicated that c6 has better bioavailability than curcumin. Therefore, these compounds may be valuable leads for the development of new anti‐inflammatory drugs.
Taking the heat off: The 24 curcumin analogues in this study were found to have no toxicity toward mouse bone marrow cells, and some of them showed potent anti‐inflammatory activity by inhibiting LPS‐stimulated TNFα, IL‐6, IL‐1β, PGE2, and NO production in rat macrophages. Pharmacokinetic studies indicated that compound c6 has better bioavailability than curcumin in vivo. Both c6 and c10 may be valuable leads for the development of new anti‐inflammatory agents. |
| doi_str_mv | 10.1002/cmdc.201600606 |
| format | Article |
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Taking the heat off: The 24 curcumin analogues in this study were found to have no toxicity toward mouse bone marrow cells, and some of them showed potent anti‐inflammatory activity by inhibiting LPS‐stimulated TNFα, IL‐6, IL‐1β, PGE2, and NO production in rat macrophages. Pharmacokinetic studies indicated that compound c6 has better bioavailability than curcumin in vivo. Both c6 and c10 may be valuable leads for the development of new anti‐inflammatory agents.</description><identifier>ISSN: 1860-7179</identifier><identifier>EISSN: 1860-7187</identifier><identifier>DOI: 10.1002/cmdc.201600606</identifier><identifier>PMID: 28098433</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Animals ; anti-inflammatory activity ; Anti-Inflammatory Agents - chemical synthesis ; Anti-Inflammatory Agents - pharmacokinetics ; Anti-Inflammatory Agents - therapeutic use ; Anti-Inflammatory Agents - toxicity ; Bone Marrow Cells - cytology ; Bone Marrow Cells - drug effects ; Bone Marrow Cells - metabolism ; Carrageenan - toxicity ; Celecoxib - pharmacology ; Celecoxib - therapeutic use ; Cell Survival - drug effects ; curcumin analogues ; Dinoprostone - metabolism ; Disease Models, Animal ; Edema - chemically induced ; Edema - drug therapy ; Enzyme-Linked Immunosorbent Assay ; Interleukin-1beta - analysis ; Interleukin-6 - analysis ; Lipopolysaccharides - toxicity ; Macrophages - cytology ; Macrophages - drug effects ; Macrophages - metabolism ; Mice ; Nitric Oxide - metabolism ; piperidones ; Piperidones - chemistry ; Piperidones - pharmacokinetics ; Piperidones - therapeutic use ; Piperidones - toxicity ; Rats ; RAW 264.7 Cells ; Rodents ; Structure-Activity Relationship ; synthesis ; Tissue Distribution ; Tumor Necrosis Factor-alpha - analysis ; Tumor necrosis factor-TNF</subject><ispartof>ChemMedChem, 2017-02, Vol.12 (4), p.327-336</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4066-4a65665d038ff15015299a90b59040091d129509a96624be494afae9284eaf493</citedby><cites>FETCH-LOGICAL-c4066-4a65665d038ff15015299a90b59040091d129509a96624be494afae9284eaf493</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%2Fcmdc.201600606$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcmdc.201600606$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28098433$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Xie, Zixin</creatorcontrib><creatorcontrib>Zhang, Zaikui</creatorcontrib><creatorcontrib>Yu, Shufang</creatorcontrib><creatorcontrib>Cheng, Donghua</creatorcontrib><creatorcontrib>Zhang, Huan</creatorcontrib><creatorcontrib>Han, Chao</creatorcontrib><creatorcontrib>Lv, Handeng</creatorcontrib><creatorcontrib>Ye, Faqing</creatorcontrib><title>Synthesis and Evaluation of Anti‐inflammatory N‐Substituted 3,5‐Bis(2‐(trifluoromethyl)benzylidene)piperidin‐4‐ones</title><title>ChemMedChem</title><addtitle>ChemMedChem</addtitle><description>A total of 24 N‐substituted 3,5‐bis(2‐(trifluoromethyl)benzylidene)piperidin‐4‐one derivatives were synthesized via aldol condensation, and their anti‐inflammatory activities were evaluated. These compounds were found to have no significant cytotoxicity against mouse bone marrow cells in vitro. However, some compounds, such as c6 (N‐(3‐methylbenzoyl)‐3,5‐bis‐(2‐(trifluoromethyl)benzylidene)piperidin‐4‐one) and c10 (N‐(2‐chlorobenzoyl)‐3,5‐bis‐(2‐(trifluoromethyl)benzylidene)piperidin‐4‐one), displayed potent anti‐inflammatory activity by inhibiting lipopolysaccharide (LPS)‐stimulated tumor necrosis factor (TNF)‐α, interleukin‐6 (IL‐6), IL‐1β, prostaglandin E2 (PGE2), and nitric oxide (NO) production in RAW 264.7 cells. Treatment with c6 or c10 at 2.5 or 10 mg kg−1 significantly decreased the paw edema induced by carrageenan in rats, and the anti‐inflammatory effects of these compounds were found to be better than those of celecoxib or indomethacin as well as their parent compound C66 (2,6‐bis‐(2‐(trifluoromethyl)benzylidene)cyclohexanone). Pharmacokinetic analysis indicated that c6 has better bioavailability than curcumin. Therefore, these compounds may be valuable leads for the development of new anti‐inflammatory drugs.
Taking the heat off: The 24 curcumin analogues in this study were found to have no toxicity toward mouse bone marrow cells, and some of them showed potent anti‐inflammatory activity by inhibiting LPS‐stimulated TNFα, IL‐6, IL‐1β, PGE2, and NO production in rat macrophages. Pharmacokinetic studies indicated that compound c6 has better bioavailability than curcumin in vivo. Both c6 and c10 may be valuable leads for the development of new anti‐inflammatory agents.</description><subject>Animals</subject><subject>anti-inflammatory activity</subject><subject>Anti-Inflammatory Agents - chemical synthesis</subject><subject>Anti-Inflammatory Agents - pharmacokinetics</subject><subject>Anti-Inflammatory Agents - therapeutic use</subject><subject>Anti-Inflammatory Agents - toxicity</subject><subject>Bone Marrow Cells - cytology</subject><subject>Bone Marrow Cells - drug effects</subject><subject>Bone Marrow Cells - metabolism</subject><subject>Carrageenan - toxicity</subject><subject>Celecoxib - pharmacology</subject><subject>Celecoxib - therapeutic use</subject><subject>Cell Survival - drug effects</subject><subject>curcumin analogues</subject><subject>Dinoprostone - metabolism</subject><subject>Disease Models, Animal</subject><subject>Edema - chemically induced</subject><subject>Edema - drug therapy</subject><subject>Enzyme-Linked Immunosorbent Assay</subject><subject>Interleukin-1beta - analysis</subject><subject>Interleukin-6 - analysis</subject><subject>Lipopolysaccharides - toxicity</subject><subject>Macrophages - cytology</subject><subject>Macrophages - drug effects</subject><subject>Macrophages - metabolism</subject><subject>Mice</subject><subject>Nitric Oxide - metabolism</subject><subject>piperidones</subject><subject>Piperidones - chemistry</subject><subject>Piperidones - pharmacokinetics</subject><subject>Piperidones - therapeutic use</subject><subject>Piperidones - toxicity</subject><subject>Rats</subject><subject>RAW 264.7 Cells</subject><subject>Rodents</subject><subject>Structure-Activity Relationship</subject><subject>synthesis</subject><subject>Tissue Distribution</subject><subject>Tumor Necrosis Factor-alpha - analysis</subject><subject>Tumor necrosis factor-TNF</subject><issn>1860-7179</issn><issn>1860-7187</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkcFu1DAQhi0EoqXlyhFF4rKVuss4cbz2sd22gFTooXCOnGSsunLsxXZA6QUegWfsk9SrLYvEBSSPxvr1-dd4fkJeUVhQgPJtN_TdogTKATjwJ2SfCg7zJRXLp7v7Uu6RFzHeAjAmqHhO9koBUrCq2ic_rieXbjCaWCjXF-fflB1VMt4VXhcnLpn7n7-M01YNg0o-TMWnLFyPbUwmjQn7ojqus3Jq4qzMfZaC0Xb0wQ-YbiZ71KK7m6zp0eHR2qwxmN64DLJc3mE8JM-0shFfPvYD8uXi_PPq_fzy6t2H1cnlvGPA-ZwpXnNe91AJrWkNtC6lVBLaWgIDkLSnpawhS5yXrEUmmdIKZSkYKs1kdUBmW9918F9HjKkZTOzQWuXQj7HJC1uKSuTzHyineRgAyOibv9BbPwaXP7IxhBqYFDRTiy3VBR9jQN2sgxlUmBoKzSbFZpNis0sxP3j9aDu2A_Y7_HdsGZBb4LuxOP3Drll9PFv9MX8AwWCt5A</recordid><startdate>20170220</startdate><enddate>20170220</enddate><creator>Xie, Zixin</creator><creator>Zhang, Zaikui</creator><creator>Yu, Shufang</creator><creator>Cheng, Donghua</creator><creator>Zhang, Huan</creator><creator>Han, Chao</creator><creator>Lv, Handeng</creator><creator>Ye, Faqing</creator><general>Wiley Subscription Services, Inc</general><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>7TK</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>K9.</scope><scope>P64</scope><scope>RC3</scope><scope>7X8</scope></search><sort><creationdate>20170220</creationdate><title>Synthesis and Evaluation of Anti‐inflammatory N‐Substituted 3,5‐Bis(2‐(trifluoromethyl)benzylidene)piperidin‐4‐ones</title><author>Xie, Zixin ; Zhang, Zaikui ; Yu, Shufang ; Cheng, Donghua ; Zhang, Huan ; Han, Chao ; Lv, Handeng ; Ye, Faqing</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4066-4a65665d038ff15015299a90b59040091d129509a96624be494afae9284eaf493</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Animals</topic><topic>anti-inflammatory activity</topic><topic>Anti-Inflammatory Agents - chemical synthesis</topic><topic>Anti-Inflammatory Agents - pharmacokinetics</topic><topic>Anti-Inflammatory Agents - therapeutic use</topic><topic>Anti-Inflammatory Agents - toxicity</topic><topic>Bone Marrow Cells - cytology</topic><topic>Bone Marrow Cells - drug effects</topic><topic>Bone Marrow Cells - metabolism</topic><topic>Carrageenan - toxicity</topic><topic>Celecoxib - pharmacology</topic><topic>Celecoxib - therapeutic use</topic><topic>Cell Survival - drug effects</topic><topic>curcumin analogues</topic><topic>Dinoprostone - metabolism</topic><topic>Disease Models, Animal</topic><topic>Edema - chemically induced</topic><topic>Edema - drug therapy</topic><topic>Enzyme-Linked Immunosorbent Assay</topic><topic>Interleukin-1beta - analysis</topic><topic>Interleukin-6 - analysis</topic><topic>Lipopolysaccharides - toxicity</topic><topic>Macrophages - cytology</topic><topic>Macrophages - drug effects</topic><topic>Macrophages - metabolism</topic><topic>Mice</topic><topic>Nitric Oxide - metabolism</topic><topic>piperidones</topic><topic>Piperidones - chemistry</topic><topic>Piperidones - pharmacokinetics</topic><topic>Piperidones - therapeutic use</topic><topic>Piperidones - toxicity</topic><topic>Rats</topic><topic>RAW 264.7 Cells</topic><topic>Rodents</topic><topic>Structure-Activity Relationship</topic><topic>synthesis</topic><topic>Tissue Distribution</topic><topic>Tumor Necrosis Factor-alpha - analysis</topic><topic>Tumor necrosis factor-TNF</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xie, Zixin</creatorcontrib><creatorcontrib>Zhang, Zaikui</creatorcontrib><creatorcontrib>Yu, Shufang</creatorcontrib><creatorcontrib>Cheng, Donghua</creatorcontrib><creatorcontrib>Zhang, Huan</creatorcontrib><creatorcontrib>Han, Chao</creatorcontrib><creatorcontrib>Lv, Handeng</creatorcontrib><creatorcontrib>Ye, Faqing</creatorcontrib><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>Neurosciences Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Genetics Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>ChemMedChem</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xie, Zixin</au><au>Zhang, Zaikui</au><au>Yu, Shufang</au><au>Cheng, Donghua</au><au>Zhang, Huan</au><au>Han, Chao</au><au>Lv, Handeng</au><au>Ye, Faqing</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Evaluation of Anti‐inflammatory N‐Substituted 3,5‐Bis(2‐(trifluoromethyl)benzylidene)piperidin‐4‐ones</atitle><jtitle>ChemMedChem</jtitle><addtitle>ChemMedChem</addtitle><date>2017-02-20</date><risdate>2017</risdate><volume>12</volume><issue>4</issue><spage>327</spage><epage>336</epage><pages>327-336</pages><issn>1860-7179</issn><eissn>1860-7187</eissn><abstract>A total of 24 N‐substituted 3,5‐bis(2‐(trifluoromethyl)benzylidene)piperidin‐4‐one derivatives were synthesized via aldol condensation, and their anti‐inflammatory activities were evaluated. These compounds were found to have no significant cytotoxicity against mouse bone marrow cells in vitro. However, some compounds, such as c6 (N‐(3‐methylbenzoyl)‐3,5‐bis‐(2‐(trifluoromethyl)benzylidene)piperidin‐4‐one) and c10 (N‐(2‐chlorobenzoyl)‐3,5‐bis‐(2‐(trifluoromethyl)benzylidene)piperidin‐4‐one), displayed potent anti‐inflammatory activity by inhibiting lipopolysaccharide (LPS)‐stimulated tumor necrosis factor (TNF)‐α, interleukin‐6 (IL‐6), IL‐1β, prostaglandin E2 (PGE2), and nitric oxide (NO) production in RAW 264.7 cells. Treatment with c6 or c10 at 2.5 or 10 mg kg−1 significantly decreased the paw edema induced by carrageenan in rats, and the anti‐inflammatory effects of these compounds were found to be better than those of celecoxib or indomethacin as well as their parent compound C66 (2,6‐bis‐(2‐(trifluoromethyl)benzylidene)cyclohexanone). Pharmacokinetic analysis indicated that c6 has better bioavailability than curcumin. Therefore, these compounds may be valuable leads for the development of new anti‐inflammatory drugs.
Taking the heat off: The 24 curcumin analogues in this study were found to have no toxicity toward mouse bone marrow cells, and some of them showed potent anti‐inflammatory activity by inhibiting LPS‐stimulated TNFα, IL‐6, IL‐1β, PGE2, and NO production in rat macrophages. Pharmacokinetic studies indicated that compound c6 has better bioavailability than curcumin in vivo. Both c6 and c10 may be valuable leads for the development of new anti‐inflammatory agents.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>28098433</pmid><doi>10.1002/cmdc.201600606</doi><tpages>10</tpages></addata></record> |
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| subjects | Animals anti-inflammatory activity Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents - pharmacokinetics Anti-Inflammatory Agents - therapeutic use Anti-Inflammatory Agents - toxicity Bone Marrow Cells - cytology Bone Marrow Cells - drug effects Bone Marrow Cells - metabolism Carrageenan - toxicity Celecoxib - pharmacology Celecoxib - therapeutic use Cell Survival - drug effects curcumin analogues Dinoprostone - metabolism Disease Models, Animal Edema - chemically induced Edema - drug therapy Enzyme-Linked Immunosorbent Assay Interleukin-1beta - analysis Interleukin-6 - analysis Lipopolysaccharides - toxicity Macrophages - cytology Macrophages - drug effects Macrophages - metabolism Mice Nitric Oxide - metabolism piperidones Piperidones - chemistry Piperidones - pharmacokinetics Piperidones - therapeutic use Piperidones - toxicity Rats RAW 264.7 Cells Rodents Structure-Activity Relationship synthesis Tissue Distribution Tumor Necrosis Factor-alpha - analysis Tumor necrosis factor-TNF |
| title | Synthesis and Evaluation of Anti‐inflammatory N‐Substituted 3,5‐Bis(2‐(trifluoromethyl)benzylidene)piperidin‐4‐ones |
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