Novel Anti-inflammatory Agents Based on Pyrazole Based Dimeric Compounds; Design, Synthesis, Docking and in Vivo Activity
Series of pyrazole ester prodrugs analogues have been synthesized and found to contain highly potent inhibitors of the cyclooxygenase-2 (COX-2) enzyme. The paper describes synthesis of the target pyrazole analogues. The structure of the synthesized mutual ester prodrugs (6—8c) were confirmed by 1H-,...
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| Veröffentlicht in: | Chemical & Pharmaceutical Bulletin 2010/05/01, Vol.58(5), pp.634-638 |
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| container_title | Chemical & Pharmaceutical Bulletin |
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| creator | Tewari, Ashish Kumar Srivastava, Priyanka Singh, Ved Prakash Singh, Amit Goel, Raj Kumar Mohan, Chethampadi Gopi |
| description | Series of pyrazole ester prodrugs analogues have been synthesized and found to contain highly potent inhibitors of the cyclooxygenase-2 (COX-2) enzyme. The paper describes synthesis of the target pyrazole analogues. The structure of the synthesized mutual ester prodrugs (6—8c) were confirmed by 1H-, 13C-NMR mass spectroscopy (MS) and their purity were ascertained by TLC and elemental analyses. The biological in vivo evaluation of these compounds in experimental models (carrageenan-induced oedema) proved the presence of anti-inflammatory activity. Docking studies into the catalytic site of COX-2 were used to identify potential anti-inflammatory lead compounds. One lead derivative was chosen endowed with good binding energies. |
| doi_str_mv | 10.1248/cpb.58.634 |
| format | Article |
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The paper describes synthesis of the target pyrazole analogues. The structure of the synthesized mutual ester prodrugs (6—8c) were confirmed by 1H-, 13C-NMR mass spectroscopy (MS) and their purity were ascertained by TLC and elemental analyses. The biological in vivo evaluation of these compounds in experimental models (carrageenan-induced oedema) proved the presence of anti-inflammatory activity. Docking studies into the catalytic site of COX-2 were used to identify potential anti-inflammatory lead compounds. One lead derivative was chosen endowed with good binding energies.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.58.634</identifier><identifier>PMID: 20460788</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Animals ; Anti-Inflammatory Agents - chemical synthesis ; Anti-Inflammatory Agents - chemistry ; Anti-Inflammatory Agents - pharmacology ; Carrageenan ; Catalytic Domain ; cyclooxygenase ; Cyclooxygenase 2 - chemistry ; Cyclooxygenase 2 - pharmacology ; Dimerization ; docking ; Drug Design ; Edema - chemically induced ; Edema - drug therapy ; Female ; Male ; Models, Molecular ; Molecular Structure ; NMR ; prodrug ; pyrazole ; Pyrazoles - chemical synthesis ; Pyrazoles - chemistry ; Pyrazoles - pharmacology ; Rats ; Rats, Wistar ; Subcutaneous Tissue - drug effects</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2010/05/01, Vol.58(5), pp.634-638</ispartof><rights>2010 The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 2010</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c717t-7ae27d8d5ab1dfd9455eba62807e0f6dfe5f1144023070f8b214fe994c1e39e63</citedby><cites>FETCH-LOGICAL-c717t-7ae27d8d5ab1dfd9455eba62807e0f6dfe5f1144023070f8b214fe994c1e39e63</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1881,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20460788$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tewari, Ashish Kumar</creatorcontrib><creatorcontrib>Srivastava, Priyanka</creatorcontrib><creatorcontrib>Singh, Ved Prakash</creatorcontrib><creatorcontrib>Singh, Amit</creatorcontrib><creatorcontrib>Goel, Raj Kumar</creatorcontrib><creatorcontrib>Mohan, Chethampadi Gopi</creatorcontrib><creatorcontrib>cCentre for Pharmacoinformatics</creatorcontrib><creatorcontrib>Banaras Hindu University</creatorcontrib><creatorcontrib>bDepartment of Pharmacology</creatorcontrib><creatorcontrib>aDepartment of Chemistry</creatorcontrib><creatorcontrib>IMS</creatorcontrib><creatorcontrib>National Institute of Pharmaceutical Education and Research (NIPER</creatorcontrib><creatorcontrib>Faculty of Science</creatorcontrib><title>Novel Anti-inflammatory Agents Based on Pyrazole Based Dimeric Compounds; Design, Synthesis, Docking and in Vivo Activity</title><title>Chemical & Pharmaceutical Bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Series of pyrazole ester prodrugs analogues have been synthesized and found to contain highly potent inhibitors of the cyclooxygenase-2 (COX-2) enzyme. The paper describes synthesis of the target pyrazole analogues. The structure of the synthesized mutual ester prodrugs (6—8c) were confirmed by 1H-, 13C-NMR mass spectroscopy (MS) and their purity were ascertained by TLC and elemental analyses. The biological in vivo evaluation of these compounds in experimental models (carrageenan-induced oedema) proved the presence of anti-inflammatory activity. Docking studies into the catalytic site of COX-2 were used to identify potential anti-inflammatory lead compounds. One lead derivative was chosen endowed with good binding energies.</description><subject>Animals</subject><subject>Anti-Inflammatory Agents - chemical synthesis</subject><subject>Anti-Inflammatory Agents - chemistry</subject><subject>Anti-Inflammatory Agents - pharmacology</subject><subject>Carrageenan</subject><subject>Catalytic Domain</subject><subject>cyclooxygenase</subject><subject>Cyclooxygenase 2 - chemistry</subject><subject>Cyclooxygenase 2 - pharmacology</subject><subject>Dimerization</subject><subject>docking</subject><subject>Drug Design</subject><subject>Edema - chemically induced</subject><subject>Edema - drug therapy</subject><subject>Female</subject><subject>Male</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>NMR</subject><subject>prodrug</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>Subcutaneous Tissue - drug effects</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU2P0zAQhiMEYrsLF34AssQBCW2KP2NHHFBplw9pBUh8XC3XmbQuiV3stFL21-Oq3SJx4TJjzTzzju23KJ4RPCWUq9d2u5wKNa0Yf1BMCOOyFJSyh8UEY1yXlFXsorhMaYMxFViyx8UFxbzCUqlJMX4Oe-jQzA-udL7tTN-bIcQRzVbgh4TemQQNCh59HaO5Cx2cKgvXQ3QWzUO_DTvfpDdoAcmt_DX6Nvphnc_pGi2C_eX8ChnfIOfRT7cPaGYHt3fD-KR41JouwdNTvip-vL_5Pv9Y3n758Gk-uy2tJHIopQEqG9UIsyRN29RcCFiaiiosAbdV04JoCeEcU4YlbtWSEt5CXXNLgNVQsavi5VF3G8PvHaRB9y5Z6DrjIeySloILJhRh_ycZE7jmlczki3_ITdhFn5-hSf5ZTuuKq0y9OlI2hpQitHobXW_iqAnWB-d0dk4LpbNzGX5-ktwte2jO6L1VGbg5ArnrrOmC75yHv4ttknYNvcsTWR5jobDISWqc5Q9Biew-zjpvjzqbNJgVnBeZODjbwf2dxDEcZs-dtYkaPPsDj2vACA</recordid><startdate>20100501</startdate><enddate>20100501</enddate><creator>Tewari, Ashish Kumar</creator><creator>Srivastava, Priyanka</creator><creator>Singh, Ved Prakash</creator><creator>Singh, Amit</creator><creator>Goel, Raj Kumar</creator><creator>Mohan, Chethampadi Gopi</creator><general>The Pharmaceutical Society of Japan</general><general>Pharmaceutical Society of Japan</general><general>Japan Science and Technology Agency</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>7TK</scope><scope>7TM</scope><scope>7U9</scope><scope>H94</scope><scope>7X8</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20100501</creationdate><title>Novel Anti-inflammatory Agents Based on Pyrazole Based Dimeric Compounds; Design, Synthesis, Docking and in Vivo Activity</title><author>Tewari, Ashish Kumar ; Srivastava, Priyanka ; Singh, Ved Prakash ; Singh, Amit ; Goel, Raj Kumar ; Mohan, Chethampadi Gopi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c717t-7ae27d8d5ab1dfd9455eba62807e0f6dfe5f1144023070f8b214fe994c1e39e63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Animals</topic><topic>Anti-Inflammatory Agents - chemical synthesis</topic><topic>Anti-Inflammatory Agents - chemistry</topic><topic>Anti-Inflammatory Agents - pharmacology</topic><topic>Carrageenan</topic><topic>Catalytic Domain</topic><topic>cyclooxygenase</topic><topic>Cyclooxygenase 2 - chemistry</topic><topic>Cyclooxygenase 2 - pharmacology</topic><topic>Dimerization</topic><topic>docking</topic><topic>Drug Design</topic><topic>Edema - chemically induced</topic><topic>Edema - drug therapy</topic><topic>Female</topic><topic>Male</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>NMR</topic><topic>prodrug</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>Subcutaneous Tissue - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tewari, Ashish Kumar</creatorcontrib><creatorcontrib>Srivastava, Priyanka</creatorcontrib><creatorcontrib>Singh, Ved Prakash</creatorcontrib><creatorcontrib>Singh, Amit</creatorcontrib><creatorcontrib>Goel, Raj Kumar</creatorcontrib><creatorcontrib>Mohan, Chethampadi Gopi</creatorcontrib><creatorcontrib>cCentre for Pharmacoinformatics</creatorcontrib><creatorcontrib>Banaras Hindu University</creatorcontrib><creatorcontrib>bDepartment of Pharmacology</creatorcontrib><creatorcontrib>aDepartment of Chemistry</creatorcontrib><creatorcontrib>IMS</creatorcontrib><creatorcontrib>National Institute of Pharmaceutical Education and Research (NIPER</creatorcontrib><creatorcontrib>Faculty of Science</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Neurosciences Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</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>Chemical & Pharmaceutical Bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tewari, Ashish Kumar</au><au>Srivastava, Priyanka</au><au>Singh, Ved Prakash</au><au>Singh, Amit</au><au>Goel, Raj Kumar</au><au>Mohan, Chethampadi Gopi</au><aucorp>cCentre for Pharmacoinformatics</aucorp><aucorp>Banaras Hindu University</aucorp><aucorp>bDepartment of Pharmacology</aucorp><aucorp>aDepartment of Chemistry</aucorp><aucorp>IMS</aucorp><aucorp>National Institute of Pharmaceutical Education and Research (NIPER</aucorp><aucorp>Faculty of Science</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel Anti-inflammatory Agents Based on Pyrazole Based Dimeric Compounds; 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| subjects | Animals Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - pharmacology Carrageenan Catalytic Domain cyclooxygenase Cyclooxygenase 2 - chemistry Cyclooxygenase 2 - pharmacology Dimerization docking Drug Design Edema - chemically induced Edema - drug therapy Female Male Models, Molecular Molecular Structure NMR prodrug pyrazole Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrazoles - pharmacology Rats Rats, Wistar Subcutaneous Tissue - drug effects |
| title | Novel Anti-inflammatory Agents Based on Pyrazole Based Dimeric Compounds; Design, Synthesis, Docking and in Vivo Activity |
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