Synthesis and antiinflammatory and analgesic activity of 5-aroyl-6-(methylthio)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-ca rboxyl ic acids and 1-methyl-4-(methylthio)-5-aroylpyrrole-2-acetic acids
5-Aroyl-6-(methylthio)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carb oxylic acids and 1-methyl-4-(methylthio)-5-aroylpyrrole-2-acetic acids were synthesized and assayed as antiinflammatory and analgesic agents. The majority of these compounds exhibit a surprisingly low level of antiinflammatory activi...
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| Veröffentlicht in: | Journal of medicinal chemistry 1989-06, Vol.32 (6), p.1202-1207 |
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| container_title | Journal of medicinal chemistry |
| container_volume | 32 |
| creator | Muchowski, J M Galeazzi, E Greenhouse, R Guzmán, A Peréz, V Ackerman, N Ballaron, S A Rovito, J R Tomolonis, A J Young, J M |
| description | 5-Aroyl-6-(methylthio)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carb oxylic acids and 1-methyl-4-(methylthio)-5-aroylpyrrole-2-acetic acids were synthesized and assayed as antiinflammatory and analgesic agents. The majority of these compounds exhibit a surprisingly low level of antiinflammatory activity (rat carrageenan paw) but have considerable potency as analgesics (mouse phenylquinone writing). For example, the p-tolyl-substituted bicyclic and monocyclic compounds 44 and 58 are 301 and 66 times more potent than aspirin (mouse writhing) but only 3.4 and 1.5 times more potent than phenylbutazone in the antiinflammatory screen (rat paw). |
| format | Article |
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The majority of these compounds exhibit a surprisingly low level of antiinflammatory activity (rat carrageenan paw) but have considerable potency as analgesics (mouse phenylquinone writing). For example, the p-tolyl-substituted bicyclic and monocyclic compounds 44 and 58 are 301 and 66 times more potent than aspirin (mouse writhing) but only 3.4 and 1.5 times more potent than phenylbutazone in the antiinflammatory screen (rat paw).</description><identifier>ISSN: 0022-2623</identifier><identifier>PMID: 2724294</identifier><language>eng</language><publisher>United States</publisher><subject>Acetates - chemical synthesis ; Acetates - therapeutic use ; Analgesia ; Animals ; Aspirin - therapeutic use ; Benzoquinones ; Carboxylic Acids - chemical synthesis ; Carboxylic Acids - therapeutic use ; Carrageenan ; Chemical Phenomena ; Chemistry ; Edema - chemically induced ; Edema - drug therapy ; Inflammation - drug therapy ; Mice ; Molecular Structure ; Pain Measurement ; Phenylbutazone - therapeutic use ; Pyrroles - chemical synthesis ; Pyrroles - therapeutic use ; Quinones ; Rats</subject><ispartof>Journal of medicinal chemistry, 1989-06, Vol.32 (6), p.1202-1207</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/2724294$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Muchowski, J M</creatorcontrib><creatorcontrib>Galeazzi, E</creatorcontrib><creatorcontrib>Greenhouse, R</creatorcontrib><creatorcontrib>Guzmán, A</creatorcontrib><creatorcontrib>Peréz, V</creatorcontrib><creatorcontrib>Ackerman, N</creatorcontrib><creatorcontrib>Ballaron, S A</creatorcontrib><creatorcontrib>Rovito, J R</creatorcontrib><creatorcontrib>Tomolonis, A J</creatorcontrib><creatorcontrib>Young, J M</creatorcontrib><title>Synthesis and antiinflammatory and analgesic activity of 5-aroyl-6-(methylthio)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-ca rboxyl ic acids and 1-methyl-4-(methylthio)-5-aroylpyrrole-2-acetic acids</title><title>Journal of medicinal chemistry</title><addtitle>J Med Chem</addtitle><description>5-Aroyl-6-(methylthio)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carb oxylic acids and 1-methyl-4-(methylthio)-5-aroylpyrrole-2-acetic acids were synthesized and assayed as antiinflammatory and analgesic agents. The majority of these compounds exhibit a surprisingly low level of antiinflammatory activity (rat carrageenan paw) but have considerable potency as analgesics (mouse phenylquinone writing). For example, the p-tolyl-substituted bicyclic and monocyclic compounds 44 and 58 are 301 and 66 times more potent than aspirin (mouse writhing) but only 3.4 and 1.5 times more potent than phenylbutazone in the antiinflammatory screen (rat paw).</description><subject>Acetates - chemical synthesis</subject><subject>Acetates - therapeutic use</subject><subject>Analgesia</subject><subject>Animals</subject><subject>Aspirin - therapeutic use</subject><subject>Benzoquinones</subject><subject>Carboxylic Acids - chemical synthesis</subject><subject>Carboxylic Acids - therapeutic use</subject><subject>Carrageenan</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Edema - chemically induced</subject><subject>Edema - drug therapy</subject><subject>Inflammation - drug therapy</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Pain Measurement</subject><subject>Phenylbutazone - therapeutic use</subject><subject>Pyrroles - chemical synthesis</subject><subject>Pyrroles - therapeutic use</subject><subject>Quinones</subject><subject>Rats</subject><issn>0022-2623</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1989</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpVkM1KxDAUhbtQxnH0EYSuRMFAkib9WcqgjjDgwtmJlNsmtZG0qUlGzPP5YlbbWbi4XO7hnO_APYqWGFOKaEqTk-jUuXeMcUJosogWNKOMFmwZfT-H3rfSKRdDL8bxSvWNhq4Db2yYRdBvo6WOofbqU_kQmybmCKwJGqXoqpO-Ddq3ylwjckORUG0Q1qBkg4ZgrdHm5VeG1-mSiKAaYluZr6DjP6wSUz9BEwux_9S57JAfWbX0h-RZdNyAdvJ83qtod3-3W2_Q9unhcX27RQNPGIKm4qSQVcVoWjCc47zOgWdVA0AKIDUXlKRCpjXmeZbRJs_H5zVEZJzwohAyWUWXE3aw5mMvnS875WqpNfTS7F2ZFZiwNGej8WI27qtOinKwqgMbyvnpyQ_AAX5-</recordid><startdate>198906</startdate><enddate>198906</enddate><creator>Muchowski, J M</creator><creator>Galeazzi, E</creator><creator>Greenhouse, R</creator><creator>Guzmán, A</creator><creator>Peréz, V</creator><creator>Ackerman, N</creator><creator>Ballaron, S A</creator><creator>Rovito, J R</creator><creator>Tomolonis, A J</creator><creator>Young, J M</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>198906</creationdate><title>Synthesis and antiinflammatory and analgesic activity of 5-aroyl-6-(methylthio)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-ca rboxyl ic acids and 1-methyl-4-(methylthio)-5-aroylpyrrole-2-acetic acids</title><author>Muchowski, J M ; Galeazzi, E ; Greenhouse, R ; Guzmán, A ; Peréz, V ; Ackerman, N ; Ballaron, S A ; Rovito, J R ; Tomolonis, A J ; Young, J M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p534-afb519ebb426940808c8a57bfaa19a1c5d216de6c058772f88022f1d751599de3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1989</creationdate><topic>Acetates - chemical synthesis</topic><topic>Acetates - therapeutic use</topic><topic>Analgesia</topic><topic>Animals</topic><topic>Aspirin - therapeutic use</topic><topic>Benzoquinones</topic><topic>Carboxylic Acids - chemical synthesis</topic><topic>Carboxylic Acids - therapeutic use</topic><topic>Carrageenan</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Edema - chemically induced</topic><topic>Edema - drug therapy</topic><topic>Inflammation - drug therapy</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>Pain Measurement</topic><topic>Phenylbutazone - therapeutic use</topic><topic>Pyrroles - chemical synthesis</topic><topic>Pyrroles - therapeutic use</topic><topic>Quinones</topic><topic>Rats</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Muchowski, J M</creatorcontrib><creatorcontrib>Galeazzi, E</creatorcontrib><creatorcontrib>Greenhouse, R</creatorcontrib><creatorcontrib>Guzmán, A</creatorcontrib><creatorcontrib>Peréz, V</creatorcontrib><creatorcontrib>Ackerman, N</creatorcontrib><creatorcontrib>Ballaron, S A</creatorcontrib><creatorcontrib>Rovito, J R</creatorcontrib><creatorcontrib>Tomolonis, A J</creatorcontrib><creatorcontrib>Young, J M</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Muchowski, J M</au><au>Galeazzi, E</au><au>Greenhouse, R</au><au>Guzmán, A</au><au>Peréz, V</au><au>Ackerman, N</au><au>Ballaron, S A</au><au>Rovito, J R</au><au>Tomolonis, A J</au><au>Young, J M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and antiinflammatory and analgesic activity of 5-aroyl-6-(methylthio)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-ca rboxyl ic acids and 1-methyl-4-(methylthio)-5-aroylpyrrole-2-acetic acids</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J Med Chem</addtitle><date>1989-06</date><risdate>1989</risdate><volume>32</volume><issue>6</issue><spage>1202</spage><epage>1207</epage><pages>1202-1207</pages><issn>0022-2623</issn><abstract>5-Aroyl-6-(methylthio)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carb oxylic acids and 1-methyl-4-(methylthio)-5-aroylpyrrole-2-acetic acids were synthesized and assayed as antiinflammatory and analgesic agents. The majority of these compounds exhibit a surprisingly low level of antiinflammatory activity (rat carrageenan paw) but have considerable potency as analgesics (mouse phenylquinone writing). For example, the p-tolyl-substituted bicyclic and monocyclic compounds 44 and 58 are 301 and 66 times more potent than aspirin (mouse writhing) but only 3.4 and 1.5 times more potent than phenylbutazone in the antiinflammatory screen (rat paw).</abstract><cop>United States</cop><pmid>2724294</pmid><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Journal of medicinal chemistry, 1989-06, Vol.32 (6), p.1202-1207 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Acetates - chemical synthesis Acetates - therapeutic use Analgesia Animals Aspirin - therapeutic use Benzoquinones Carboxylic Acids - chemical synthesis Carboxylic Acids - therapeutic use Carrageenan Chemical Phenomena Chemistry Edema - chemically induced Edema - drug therapy Inflammation - drug therapy Mice Molecular Structure Pain Measurement Phenylbutazone - therapeutic use Pyrroles - chemical synthesis Pyrroles - therapeutic use Quinones Rats |
| title | Synthesis and antiinflammatory and analgesic activity of 5-aroyl-6-(methylthio)-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-ca rboxyl ic acids and 1-methyl-4-(methylthio)-5-aroylpyrrole-2-acetic acids |
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