Amide Derivatives of [5-Chloro-6-(2-chloro/fluorobenzoyl)-2-benzoxazolinone-3-yl]acetic Acids as Potential Analgesic and Anti-Inflammatory Compounds
In this study, we have explored the prevention of gastric side effects such as gastric lesions and bleeding while maintaining the high analgesic and anti‐inflammatory activities by the derivatization of the carboxylate moiety into amides in [5‐chloro‐6‐(2‐chloro/fluorobenzoyl)‐2‐benzoxazolinone‐3‐yl...
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| Veröffentlicht in: | Archiv der Pharmazie (Weinheim) 2003-07, Vol.336 (4-5), p.251-257 |
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| creator | Banoglu, Erden Okçelik, Berna Kupeli, Esra Ünlü, Serdar Yeşilada, Erdem Amat, Merc? Caturla, Joan F. Sahin, M. Fethi |
| description | In this study, we have explored the prevention of gastric side effects such as gastric lesions and bleeding while maintaining the high analgesic and anti‐inflammatory activities by the derivatization of the carboxylate moiety into amides in [5‐chloro‐6‐(2‐chloro/fluorobenzoyl)‐2‐benzoxazolinone‐3‐yl]acetic acids. We have tested the analgesic and anti‐inflammatory activities of the synthesized compounds in vivo by using p‐benzoquinone‐induced writhing test and carrageenan‐induced hind paw edema model, respectively. Compounds 3a, 3d, 3e, 3j and 3k potent analgesic and anti‐inflammatory activities without gastric lesions in the tested animals. Therefore, conversion of the carboxylate moiety into certain amide derivatives generated potent analgesic and anti‐inflammatory compounds while eliminating the gastrointestinal side effects. Cyclooxygenase (COX)‐selectivity of the active compounds was also investigated by using in vitro human whole blood assay. Compounds 3a, 3e, 3h and 3k selective inhibition of COX‐2 to some extent although the inhibitory activity was not very potent. |
| doi_str_mv | 10.1002/ardp.200300723 |
| format | Article |
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Fethi</creator><creatorcontrib>Banoglu, Erden ; Okçelik, Berna ; Kupeli, Esra ; Ünlü, Serdar ; Yeşilada, Erdem ; Amat, Merc? ; Caturla, Joan F. ; Sahin, M. Fethi</creatorcontrib><description>In this study, we have explored the prevention of gastric side effects such as gastric lesions and bleeding while maintaining the high analgesic and anti‐inflammatory activities by the derivatization of the carboxylate moiety into amides in [5‐chloro‐6‐(2‐chloro/fluorobenzoyl)‐2‐benzoxazolinone‐3‐yl]acetic acids. We have tested the analgesic and anti‐inflammatory activities of the synthesized compounds in vivo by using p‐benzoquinone‐induced writhing test and carrageenan‐induced hind paw edema model, respectively. Compounds 3a, 3d, 3e, 3j and 3k potent analgesic and anti‐inflammatory activities without gastric lesions in the tested animals. Therefore, conversion of the carboxylate moiety into certain amide derivatives generated potent analgesic and anti‐inflammatory compounds while eliminating the gastrointestinal side effects. Cyclooxygenase (COX)‐selectivity of the active compounds was also investigated by using in vitro human whole blood assay. Compounds 3a, 3e, 3h and 3k selective inhibition of COX‐2 to some extent although the inhibitory activity was not very potent.</description><identifier>ISSN: 0365-6233</identifier><identifier>EISSN: 1521-4184</identifier><identifier>DOI: 10.1002/ardp.200300723</identifier><identifier>PMID: 12916060</identifier><identifier>CODEN: ARPMAS</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>2-Benzoxazolinone ; Acetates - chemical synthesis ; Acetates - chemistry ; Acetates - pharmacology ; Analgesic ; Analgesics ; Analgesics - chemical synthesis ; Analgesics - chemistry ; Analgesics - pharmacology ; Analgesics - toxicity ; Animals ; Anti-inflammatory ; Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis ; Anti-Inflammatory Agents, Non-Steroidal - chemistry ; Anti-Inflammatory Agents, Non-Steroidal - pharmacology ; Anti-Inflammatory Agents, Non-Steroidal - toxicity ; Biological and medical sciences ; Bones, joints and connective tissue. Antiinflammatory agents ; COX-1 ; COX-2 ; Cyclooxygenase 1 ; Cyclooxygenase 2 ; Cyclooxygenase 2 Inhibitors ; Cyclooxygenase Inhibitors - chemical synthesis ; Cyclooxygenase Inhibitors - chemistry ; Cyclooxygenase Inhibitors - pharmacology ; Cyclooxygenase Inhibitors - toxicity ; Disease Models, Animal ; Edema - chemically induced ; Edema - drug therapy ; Humans ; In Vitro Techniques ; Isoenzymes - antagonists & inhibitors ; Isoenzymes - blood ; Lethal Dose 50 ; Male ; Medical sciences ; Membrane Proteins ; Mice ; Neuropharmacology ; Oxazoles - chemical synthesis ; Oxazoles - chemistry ; Oxazoles - pharmacology ; Pain Measurement ; Pharmacology. Drug treatments ; Prostaglandin-Endoperoxide Synthases - blood ; Stomach Ulcer - chemically induced ; Structure-Activity Relationship</subject><ispartof>Archiv der Pharmazie (Weinheim), 2003-07, Vol.336 (4-5), p.251-257</ispartof><rights>Copyright © 2003 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4093-92ab2562d97718c9f3bffafcfa0267b18a48ae2ad279b1df001c1daf63da40f13</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fardp.200300723$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fardp.200300723$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15047802$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12916060$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Banoglu, Erden</creatorcontrib><creatorcontrib>Okçelik, Berna</creatorcontrib><creatorcontrib>Kupeli, Esra</creatorcontrib><creatorcontrib>Ünlü, Serdar</creatorcontrib><creatorcontrib>Yeşilada, Erdem</creatorcontrib><creatorcontrib>Amat, Merc?</creatorcontrib><creatorcontrib>Caturla, Joan F.</creatorcontrib><creatorcontrib>Sahin, M. Fethi</creatorcontrib><title>Amide Derivatives of [5-Chloro-6-(2-chloro/fluorobenzoyl)-2-benzoxazolinone-3-yl]acetic Acids as Potential Analgesic and Anti-Inflammatory Compounds</title><title>Archiv der Pharmazie (Weinheim)</title><addtitle>Arch. Pharm. Pharm. Med. Chem</addtitle><description>In this study, we have explored the prevention of gastric side effects such as gastric lesions and bleeding while maintaining the high analgesic and anti‐inflammatory activities by the derivatization of the carboxylate moiety into amides in [5‐chloro‐6‐(2‐chloro/fluorobenzoyl)‐2‐benzoxazolinone‐3‐yl]acetic acids. We have tested the analgesic and anti‐inflammatory activities of the synthesized compounds in vivo by using p‐benzoquinone‐induced writhing test and carrageenan‐induced hind paw edema model, respectively. Compounds 3a, 3d, 3e, 3j and 3k potent analgesic and anti‐inflammatory activities without gastric lesions in the tested animals. Therefore, conversion of the carboxylate moiety into certain amide derivatives generated potent analgesic and anti‐inflammatory compounds while eliminating the gastrointestinal side effects. Cyclooxygenase (COX)‐selectivity of the active compounds was also investigated by using in vitro human whole blood assay. Compounds 3a, 3e, 3h and 3k selective inhibition of COX‐2 to some extent although the inhibitory activity was not very potent.</description><subject>2-Benzoxazolinone</subject><subject>Acetates - chemical synthesis</subject><subject>Acetates - chemistry</subject><subject>Acetates - pharmacology</subject><subject>Analgesic</subject><subject>Analgesics</subject><subject>Analgesics - chemical synthesis</subject><subject>Analgesics - chemistry</subject><subject>Analgesics - pharmacology</subject><subject>Analgesics - toxicity</subject><subject>Animals</subject><subject>Anti-inflammatory</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>Anti-Inflammatory Agents, Non-Steroidal - toxicity</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>COX-1</subject><subject>COX-2</subject><subject>Cyclooxygenase 1</subject><subject>Cyclooxygenase 2</subject><subject>Cyclooxygenase 2 Inhibitors</subject><subject>Cyclooxygenase Inhibitors - chemical synthesis</subject><subject>Cyclooxygenase Inhibitors - chemistry</subject><subject>Cyclooxygenase Inhibitors - pharmacology</subject><subject>Cyclooxygenase Inhibitors - toxicity</subject><subject>Disease Models, Animal</subject><subject>Edema - chemically induced</subject><subject>Edema - drug therapy</subject><subject>Humans</subject><subject>In Vitro Techniques</subject><subject>Isoenzymes - antagonists & inhibitors</subject><subject>Isoenzymes - blood</subject><subject>Lethal Dose 50</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Membrane Proteins</subject><subject>Mice</subject><subject>Neuropharmacology</subject><subject>Oxazoles - chemical synthesis</subject><subject>Oxazoles - chemistry</subject><subject>Oxazoles - pharmacology</subject><subject>Pain Measurement</subject><subject>Pharmacology. Drug treatments</subject><subject>Prostaglandin-Endoperoxide Synthases - blood</subject><subject>Stomach Ulcer - chemically induced</subject><subject>Structure-Activity Relationship</subject><issn>0365-6233</issn><issn>1521-4184</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1v1DAQhiMEokvhyhHlggQHb8d2Po9pSkulClYIygEha-IPMDjxys62TX8HP5hsd9Vy4zTvaJ53ZvQmyUsKSwrAjjCo9ZIBcICS8UfJguaMkoxW2eNkAbzIScE4P0iexfgLthjLnyYHlNW0gAIWyZ-mt0qnJzrYKxztlY6pN-m3nLQ_nQ-eFOQNI_JOHxm3mUunh1s_ubeEkTt5g7fe2cEPmnAyue8o9Whl2kirYooxXflRD6NFlzYDuh86zkMc1NyNlpwPxmHf4-jDlLa-X_vNoOLz5IlBF_WLfT1Mvpy--9y-Jxcfz87b5oLIDGpOaoYdywum6rKklawN74xBIw0CK8qOVphVqBkqVtYdVQaASqrQFFxhBobyw2S52yuDjzFoI9bB9hgmQUFs4xXbeMV9vLPh1c6w3nS9Vg_4Ps8ZeL0HMEp0JuAgbXzgcsjKCtjM1Tvu2jo9_eesaD6drP59guy8No765t6L4bcoSl7m4uuHM1Fe5pctPwax4n8BTD6lLw</recordid><startdate>200307</startdate><enddate>200307</enddate><creator>Banoglu, Erden</creator><creator>Okçelik, Berna</creator><creator>Kupeli, Esra</creator><creator>Ünlü, Serdar</creator><creator>Yeşilada, Erdem</creator><creator>Amat, Merc?</creator><creator>Caturla, Joan F.</creator><creator>Sahin, M. Fethi</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</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></search><sort><creationdate>200307</creationdate><title>Amide Derivatives of [5-Chloro-6-(2-chloro/fluorobenzoyl)-2-benzoxazolinone-3-yl]acetic Acids as Potential Analgesic and Anti-Inflammatory Compounds</title><author>Banoglu, Erden ; Okçelik, Berna ; Kupeli, Esra ; Ünlü, Serdar ; Yeşilada, Erdem ; Amat, Merc? ; Caturla, Joan F. ; Sahin, M. Fethi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4093-92ab2562d97718c9f3bffafcfa0267b18a48ae2ad279b1df001c1daf63da40f13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>2-Benzoxazolinone</topic><topic>Acetates - chemical synthesis</topic><topic>Acetates - chemistry</topic><topic>Acetates - pharmacology</topic><topic>Analgesic</topic><topic>Analgesics</topic><topic>Analgesics - chemical synthesis</topic><topic>Analgesics - chemistry</topic><topic>Analgesics - pharmacology</topic><topic>Analgesics - toxicity</topic><topic>Animals</topic><topic>Anti-inflammatory</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>Anti-Inflammatory Agents, Non-Steroidal - toxicity</topic><topic>Biological and medical sciences</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>COX-1</topic><topic>COX-2</topic><topic>Cyclooxygenase 1</topic><topic>Cyclooxygenase 2</topic><topic>Cyclooxygenase 2 Inhibitors</topic><topic>Cyclooxygenase Inhibitors - chemical synthesis</topic><topic>Cyclooxygenase Inhibitors - chemistry</topic><topic>Cyclooxygenase Inhibitors - pharmacology</topic><topic>Cyclooxygenase Inhibitors - toxicity</topic><topic>Disease Models, Animal</topic><topic>Edema - chemically induced</topic><topic>Edema - drug therapy</topic><topic>Humans</topic><topic>In Vitro Techniques</topic><topic>Isoenzymes - antagonists & inhibitors</topic><topic>Isoenzymes - blood</topic><topic>Lethal Dose 50</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Membrane Proteins</topic><topic>Mice</topic><topic>Neuropharmacology</topic><topic>Oxazoles - chemical synthesis</topic><topic>Oxazoles - chemistry</topic><topic>Oxazoles - pharmacology</topic><topic>Pain Measurement</topic><topic>Pharmacology. Drug treatments</topic><topic>Prostaglandin-Endoperoxide Synthases - blood</topic><topic>Stomach Ulcer - chemically induced</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Banoglu, Erden</creatorcontrib><creatorcontrib>Okçelik, Berna</creatorcontrib><creatorcontrib>Kupeli, Esra</creatorcontrib><creatorcontrib>Ünlü, Serdar</creatorcontrib><creatorcontrib>Yeşilada, Erdem</creatorcontrib><creatorcontrib>Amat, Merc?</creatorcontrib><creatorcontrib>Caturla, Joan F.</creatorcontrib><creatorcontrib>Sahin, M. Fethi</creatorcontrib><collection>Istex</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><jtitle>Archiv der Pharmazie (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Banoglu, Erden</au><au>Okçelik, Berna</au><au>Kupeli, Esra</au><au>Ünlü, Serdar</au><au>Yeşilada, Erdem</au><au>Amat, Merc?</au><au>Caturla, Joan F.</au><au>Sahin, M. Fethi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Amide Derivatives of [5-Chloro-6-(2-chloro/fluorobenzoyl)-2-benzoxazolinone-3-yl]acetic Acids as Potential Analgesic and Anti-Inflammatory Compounds</atitle><jtitle>Archiv der Pharmazie (Weinheim)</jtitle><addtitle>Arch. Pharm. Pharm. Med. Chem</addtitle><date>2003-07</date><risdate>2003</risdate><volume>336</volume><issue>4-5</issue><spage>251</spage><epage>257</epage><pages>251-257</pages><issn>0365-6233</issn><eissn>1521-4184</eissn><coden>ARPMAS</coden><abstract>In this study, we have explored the prevention of gastric side effects such as gastric lesions and bleeding while maintaining the high analgesic and anti‐inflammatory activities by the derivatization of the carboxylate moiety into amides in [5‐chloro‐6‐(2‐chloro/fluorobenzoyl)‐2‐benzoxazolinone‐3‐yl]acetic acids. We have tested the analgesic and anti‐inflammatory activities of the synthesized compounds in vivo by using p‐benzoquinone‐induced writhing test and carrageenan‐induced hind paw edema model, respectively. Compounds 3a, 3d, 3e, 3j and 3k potent analgesic and anti‐inflammatory activities without gastric lesions in the tested animals. Therefore, conversion of the carboxylate moiety into certain amide derivatives generated potent analgesic and anti‐inflammatory compounds while eliminating the gastrointestinal side effects. Cyclooxygenase (COX)‐selectivity of the active compounds was also investigated by using in vitro human whole blood assay. Compounds 3a, 3e, 3h and 3k selective inhibition of COX‐2 to some extent although the inhibitory activity was not very potent.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>12916060</pmid><doi>10.1002/ardp.200300723</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0365-6233 |
| ispartof | Archiv der Pharmazie (Weinheim), 2003-07, Vol.336 (4-5), p.251-257 |
| issn | 0365-6233 1521-4184 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_ardp_200300723 |
| source | MEDLINE; Wiley Online Library All Journals |
| subjects | 2-Benzoxazolinone Acetates - chemical synthesis Acetates - chemistry Acetates - pharmacology Analgesic Analgesics Analgesics - chemical synthesis Analgesics - chemistry Analgesics - pharmacology Analgesics - toxicity Animals Anti-inflammatory Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis Anti-Inflammatory Agents, Non-Steroidal - chemistry Anti-Inflammatory Agents, Non-Steroidal - pharmacology Anti-Inflammatory Agents, Non-Steroidal - toxicity Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents COX-1 COX-2 Cyclooxygenase 1 Cyclooxygenase 2 Cyclooxygenase 2 Inhibitors Cyclooxygenase Inhibitors - chemical synthesis Cyclooxygenase Inhibitors - chemistry Cyclooxygenase Inhibitors - pharmacology Cyclooxygenase Inhibitors - toxicity Disease Models, Animal Edema - chemically induced Edema - drug therapy Humans In Vitro Techniques Isoenzymes - antagonists & inhibitors Isoenzymes - blood Lethal Dose 50 Male Medical sciences Membrane Proteins Mice Neuropharmacology Oxazoles - chemical synthesis Oxazoles - chemistry Oxazoles - pharmacology Pain Measurement Pharmacology. Drug treatments Prostaglandin-Endoperoxide Synthases - blood Stomach Ulcer - chemically induced Structure-Activity Relationship |
| title | Amide Derivatives of [5-Chloro-6-(2-chloro/fluorobenzoyl)-2-benzoxazolinone-3-yl]acetic Acids as Potential Analgesic and Anti-Inflammatory Compounds |
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