Synthesis, biological evaluation and molecular modeling study of pyrazole derivatives as selective COX-2 inhibitors and anti-inflammatory agents
•Pyrazole derivatives were synthesized.•In vivo anti-inflammatory activity was evaluated.•Carrageenan-induced rat paw edema model was used.•In silico (docking) studies were carried out.•Theoretical binding was calculated on schrodinger software. A novel series of pyrazole derivatives were synthesize...
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| Veröffentlicht in: | Bioorganic chemistry 2014-10, Vol.56, p.8-15 |
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| container_title | Bioorganic chemistry |
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| creator | Tewari, Ashish Kumar Singh, Ved Prakash Yadav, Pratima Gupta, Garima Singh, Amit Goel, Raj Kumar Shinde, Pravin Mohan, C. Gopi |
| description | •Pyrazole derivatives were synthesized.•In vivo anti-inflammatory activity was evaluated.•Carrageenan-induced rat paw edema model was used.•In silico (docking) studies were carried out.•Theoretical binding was calculated on schrodinger software.
A novel series of pyrazole derivatives were synthesized and evaluated in vivo for their anti-inflammatory activity in carrageenan-induced rat paw edema model. Among all compounds, 5a, and 5b showed comparable anti-inflammatory activity to Nimesulide, the standard drug taken for the studies. In silico (docking) studies were carried out to investigate the theoretical binding mode of the compounds to target the cyclooxygenase (COX-2) using Autodock 4.2. |
| doi_str_mv | 10.1016/j.bioorg.2014.05.004 |
| format | Article |
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A novel series of pyrazole derivatives were synthesized and evaluated in vivo for their anti-inflammatory activity in carrageenan-induced rat paw edema model. Among all compounds, 5a, and 5b showed comparable anti-inflammatory activity to Nimesulide, the standard drug taken for the studies. In silico (docking) studies were carried out to investigate the theoretical binding mode of the compounds to target the cyclooxygenase (COX-2) using Autodock 4.2.</description><identifier>ISSN: 0045-2068</identifier><identifier>EISSN: 1090-2120</identifier><identifier>DOI: 10.1016/j.bioorg.2014.05.004</identifier><identifier>PMID: 24893208</identifier><language>eng</language><publisher>United States: Elsevier Inc</publisher><subject>Animals ; Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis ; Anti-Inflammatory Agents, Non-Steroidal - chemistry ; Anti-Inflammatory Agents, Non-Steroidal - pharmacology ; COX-2 inhibitors ; Cyclooxygenase 1 - metabolism ; Cyclooxygenase 2 - metabolism ; Cyclooxygenase Inhibitors - chemical synthesis ; Cyclooxygenase Inhibitors - chemistry ; Cyclooxygenase Inhibitors - pharmacology ; Dose-Response Relationship, Drug ; Drug design ; Edema - drug therapy ; Humans ; Inflammation ; Models, Molecular ; Molecular modeling ; Molecular Structure ; Pyrazole ; Pyrazoles - chemical synthesis ; Pyrazoles - chemistry ; Pyrazoles - pharmacology ; Rats ; Rats, Wistar ; Structure-Activity Relationship</subject><ispartof>Bioorganic chemistry, 2014-10, Vol.56, p.8-15</ispartof><rights>2014 Elsevier Inc.</rights><rights>Copyright © 2014 Elsevier Inc. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c428t-eee4d3880907f21a14bdf7a77e6f94d48eaa7877d3a02479bf58b737a1abcaf33</citedby><cites>FETCH-LOGICAL-c428t-eee4d3880907f21a14bdf7a77e6f94d48eaa7877d3a02479bf58b737a1abcaf33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bioorg.2014.05.004$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27923,27924,45994</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24893208$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tewari, Ashish Kumar</creatorcontrib><creatorcontrib>Singh, Ved Prakash</creatorcontrib><creatorcontrib>Yadav, Pratima</creatorcontrib><creatorcontrib>Gupta, Garima</creatorcontrib><creatorcontrib>Singh, Amit</creatorcontrib><creatorcontrib>Goel, Raj Kumar</creatorcontrib><creatorcontrib>Shinde, Pravin</creatorcontrib><creatorcontrib>Mohan, C. Gopi</creatorcontrib><title>Synthesis, biological evaluation and molecular modeling study of pyrazole derivatives as selective COX-2 inhibitors and anti-inflammatory agents</title><title>Bioorganic chemistry</title><addtitle>Bioorg Chem</addtitle><description>•Pyrazole derivatives were synthesized.•In vivo anti-inflammatory activity was evaluated.•Carrageenan-induced rat paw edema model was used.•In silico (docking) studies were carried out.•Theoretical binding was calculated on schrodinger software.
A novel series of pyrazole derivatives were synthesized and evaluated in vivo for their anti-inflammatory activity in carrageenan-induced rat paw edema model. Among all compounds, 5a, and 5b showed comparable anti-inflammatory activity to Nimesulide, the standard drug taken for the studies. In silico (docking) studies were carried out to investigate the theoretical binding mode of the compounds to target the cyclooxygenase (COX-2) using Autodock 4.2.</description><subject>Animals</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - chemistry</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - pharmacology</subject><subject>COX-2 inhibitors</subject><subject>Cyclooxygenase 1 - metabolism</subject><subject>Cyclooxygenase 2 - metabolism</subject><subject>Cyclooxygenase Inhibitors - chemical synthesis</subject><subject>Cyclooxygenase Inhibitors - chemistry</subject><subject>Cyclooxygenase Inhibitors - pharmacology</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug design</subject><subject>Edema - drug therapy</subject><subject>Humans</subject><subject>Inflammation</subject><subject>Models, Molecular</subject><subject>Molecular modeling</subject><subject>Molecular Structure</subject><subject>Pyrazole</subject><subject>Pyrazoles - chemical synthesis</subject><subject>Pyrazoles - chemistry</subject><subject>Pyrazoles - pharmacology</subject><subject>Rats</subject><subject>Rats, Wistar</subject><subject>Structure-Activity Relationship</subject><issn>0045-2068</issn><issn>1090-2120</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9UcuO1DAQtBCIHRb-ACEfOZBgO06cuSCh0fKQVtoDIHGzOnF71iPHHuxkpPAVfDIeZuHIye3uqmp1FSEvOas5493bQz24GNO-FozLmrU1Y_IR2XC2ZZXggj0mm9JpK8G6_oo8y_nAGOdSdU_JlZD9thGs35BfX9Yw32N2-Q0tej7u3Qie4gn8ArOLgUIwdIoex8VDKpVB78Ke5nkxK42WHtcEP8ucGkzuVDgnzBQyzVg45x_d3X2vBHXh3g1ujin_kYQwu8oF62GaoHRXCnsMc35OnljwGV88vNfk24ebr7tP1e3dx8-797fVKEU_V4goTdP35VplBQcuB2MVKIWd3UojewRQvVKmASak2g627QfVKOAwjGCb5pq8vugeU_yxYJ715PKI3kPAuGTN266YxZQSBSov0DHFnBNafUxugrRqzvQ5C33Qlyz0OQvNWl2cL7RXDxuWYULzj_TX_AJ4dwFgufPkMOk8OgwjGpeKddpE9_8NvwFWdKB0</recordid><startdate>20141001</startdate><enddate>20141001</enddate><creator>Tewari, Ashish Kumar</creator><creator>Singh, Ved Prakash</creator><creator>Yadav, Pratima</creator><creator>Gupta, Garima</creator><creator>Singh, Amit</creator><creator>Goel, Raj Kumar</creator><creator>Shinde, Pravin</creator><creator>Mohan, C. Gopi</creator><general>Elsevier 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>7X8</scope></search><sort><creationdate>20141001</creationdate><title>Synthesis, biological evaluation and molecular modeling study of pyrazole derivatives as selective COX-2 inhibitors and anti-inflammatory agents</title><author>Tewari, Ashish Kumar ; Singh, Ved Prakash ; Yadav, Pratima ; Gupta, Garima ; Singh, Amit ; Goel, Raj Kumar ; Shinde, Pravin ; Mohan, C. Gopi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c428t-eee4d3880907f21a14bdf7a77e6f94d48eaa7877d3a02479bf58b737a1abcaf33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Animals</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - chemistry</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - pharmacology</topic><topic>COX-2 inhibitors</topic><topic>Cyclooxygenase 1 - metabolism</topic><topic>Cyclooxygenase 2 - metabolism</topic><topic>Cyclooxygenase Inhibitors - chemical synthesis</topic><topic>Cyclooxygenase Inhibitors - chemistry</topic><topic>Cyclooxygenase Inhibitors - pharmacology</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug design</topic><topic>Edema - drug therapy</topic><topic>Humans</topic><topic>Inflammation</topic><topic>Models, Molecular</topic><topic>Molecular modeling</topic><topic>Molecular Structure</topic><topic>Pyrazole</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - chemistry</topic><topic>Pyrazoles - pharmacology</topic><topic>Rats</topic><topic>Rats, Wistar</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tewari, Ashish Kumar</creatorcontrib><creatorcontrib>Singh, Ved Prakash</creatorcontrib><creatorcontrib>Yadav, Pratima</creatorcontrib><creatorcontrib>Gupta, Garima</creatorcontrib><creatorcontrib>Singh, Amit</creatorcontrib><creatorcontrib>Goel, Raj Kumar</creatorcontrib><creatorcontrib>Shinde, Pravin</creatorcontrib><creatorcontrib>Mohan, C. 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Gopi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, biological evaluation and molecular modeling study of pyrazole derivatives as selective COX-2 inhibitors and anti-inflammatory agents</atitle><jtitle>Bioorganic chemistry</jtitle><addtitle>Bioorg Chem</addtitle><date>2014-10-01</date><risdate>2014</risdate><volume>56</volume><spage>8</spage><epage>15</epage><pages>8-15</pages><issn>0045-2068</issn><eissn>1090-2120</eissn><abstract>•Pyrazole derivatives were synthesized.•In vivo anti-inflammatory activity was evaluated.•Carrageenan-induced rat paw edema model was used.•In silico (docking) studies were carried out.•Theoretical binding was calculated on schrodinger software.
A novel series of pyrazole derivatives were synthesized and evaluated in vivo for their anti-inflammatory activity in carrageenan-induced rat paw edema model. Among all compounds, 5a, and 5b showed comparable anti-inflammatory activity to Nimesulide, the standard drug taken for the studies. In silico (docking) studies were carried out to investigate the theoretical binding mode of the compounds to target the cyclooxygenase (COX-2) using Autodock 4.2.</abstract><cop>United States</cop><pub>Elsevier Inc</pub><pmid>24893208</pmid><doi>10.1016/j.bioorg.2014.05.004</doi><tpages>8</tpages></addata></record> |
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| subjects | Animals Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis Anti-Inflammatory Agents, Non-Steroidal - chemistry Anti-Inflammatory Agents, Non-Steroidal - pharmacology COX-2 inhibitors Cyclooxygenase 1 - metabolism Cyclooxygenase 2 - metabolism Cyclooxygenase Inhibitors - chemical synthesis Cyclooxygenase Inhibitors - chemistry Cyclooxygenase Inhibitors - pharmacology Dose-Response Relationship, Drug Drug design Edema - drug therapy Humans Inflammation Models, Molecular Molecular modeling Molecular Structure Pyrazole Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrazoles - pharmacology Rats Rats, Wistar Structure-Activity Relationship |
| title | Synthesis, biological evaluation and molecular modeling study of pyrazole derivatives as selective COX-2 inhibitors and anti-inflammatory agents |
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