4-(6-Methoxy-2-naphthyl)butan-2-one and related analogs, a novel structural class of antiinflammatory compounds
A series of compounds related to 4-(6-methoxy-2-naphthyl)butan-2-one has been prepared and tested for antiinflammatory activity by the cotton pellet granuloma method. Compounds possessing a small lipophilic group such as methoxyl, methyl, or chloro in the 6 position in conjunction with a butan-2-one...
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Veröffentlicht in: | Journal of medicinal chemistry 1978-12, Vol.21 (12), p.1260-1264 |
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container_issue | 12 |
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container_title | Journal of medicinal chemistry |
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creator | Goudie, Alexander C Gaster, Laramie M Lake, Antony W Rose, Carl J Freeman, Patricia C Hughes, Bryn O Miller, David |
description | A series of compounds related to 4-(6-methoxy-2-naphthyl)butan-2-one has been prepared and tested for antiinflammatory activity by the cotton pellet granuloma method. Compounds possessing a small lipophilic group such as methoxyl, methyl, or chloro in the 6 position in conjunction with a butan-2-one side chain in the 2 position of the naphthalene ring were most active. The indtroduction of a methyl group along the side chain was invariably deleterious. Good activity was generally retained by forming esters of a butan-2-ol side chain. |
doi_str_mv | 10.1021/jm00210a016 |
format | Article |
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Compounds possessing a small lipophilic group such as methoxyl, methyl, or chloro in the 6 position in conjunction with a butan-2-one side chain in the 2 position of the naphthalene ring were most active. The indtroduction of a methyl group along the side chain was invariably deleterious. 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Good activity was generally retained by forming esters of a butan-2-ol side chain.</description><subject>Animals</subject><subject>Anti-Inflammatory Agents - chemical synthesis</subject><subject>Female</subject><subject>Gossypium</subject><subject>Granuloma - etiology</subject><subject>Granuloma - physiopathology</subject><subject>Naphthalenes - chemical synthesis</subject><subject>Naphthalenes - pharmacology</subject><subject>Rats</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1978</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEtv1DAUhS3Eayis2LLIiofA4FfiZFlV0FYqBcQg2Fl37BsmgxNPbQd1_j1GqSoWrM7VOZ_OlQ4hTzl7y5ng73YjK8KA8eYOWfFaMKpapu6SVfEFFY2QD8mjlHaMMcmFfEDuayG0VCsSFH3Z0I-Yt-H6QAWdYL_N24N_tZkzTMUIE1YwuSqih4yu3ODDz_SmgmoKv9FXKcfZ5jmCr6yHlKrQFygPw9R7GEfIIR4qG8Z9mCeXHpN7PfiET270iHz78H59ckYvPp2enxxfUJBSZdrxFrjdNEK3jRMt2r5Gp7BTqBS0FhnWuu64BNw4W2tsOOvAMdeDlrZ1vTwiz5fefQxXM6ZsxiFZ9B4mDHMyWomG13VXwNcLaGNIKWJv9nEYIR4MZ-bvuuafdQv97KZ23ozobtllzhLTJR5SxuvbFOIv02ipa7P-_NX8uFzzL9_bS3Na-BcLDzaZXZhjGTf99_EfwgGRnQ</recordid><startdate>197812</startdate><enddate>197812</enddate><creator>Goudie, Alexander C</creator><creator>Gaster, Laramie M</creator><creator>Lake, Antony W</creator><creator>Rose, Carl J</creator><creator>Freeman, Patricia C</creator><creator>Hughes, Bryn O</creator><creator>Miller, David</creator><general>American Chemical Society</general><scope>BSCLL</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><scope>7X8</scope></search><sort><creationdate>197812</creationdate><title>4-(6-Methoxy-2-naphthyl)butan-2-one and related analogs, a novel structural class of antiinflammatory compounds</title><author>Goudie, Alexander C ; Gaster, Laramie M ; Lake, Antony W ; Rose, Carl J ; Freeman, Patricia C ; Hughes, Bryn O ; Miller, David</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a334t-918a1cb62786d28ecf5ed4e94e44a8ce0e575913aebdc57e6109ad0dfa73c8df3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1978</creationdate><topic>Animals</topic><topic>Anti-Inflammatory Agents - chemical synthesis</topic><topic>Female</topic><topic>Gossypium</topic><topic>Granuloma - etiology</topic><topic>Granuloma - physiopathology</topic><topic>Naphthalenes - chemical synthesis</topic><topic>Naphthalenes - pharmacology</topic><topic>Rats</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Goudie, Alexander C</creatorcontrib><creatorcontrib>Gaster, Laramie M</creatorcontrib><creatorcontrib>Lake, Antony W</creatorcontrib><creatorcontrib>Rose, Carl J</creatorcontrib><creatorcontrib>Freeman, Patricia C</creatorcontrib><creatorcontrib>Hughes, Bryn O</creatorcontrib><creatorcontrib>Miller, David</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Goudie, Alexander C</au><au>Gaster, Laramie M</au><au>Lake, Antony W</au><au>Rose, Carl J</au><au>Freeman, Patricia C</au><au>Hughes, Bryn O</au><au>Miller, David</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>4-(6-Methoxy-2-naphthyl)butan-2-one and related analogs, a novel structural class of antiinflammatory compounds</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1978-12</date><risdate>1978</risdate><volume>21</volume><issue>12</issue><spage>1260</spage><epage>1264</epage><pages>1260-1264</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><abstract>A series of compounds related to 4-(6-methoxy-2-naphthyl)butan-2-one has been prepared and tested for antiinflammatory activity by the cotton pellet granuloma method. Compounds possessing a small lipophilic group such as methoxyl, methyl, or chloro in the 6 position in conjunction with a butan-2-one side chain in the 2 position of the naphthalene ring were most active. The indtroduction of a methyl group along the side chain was invariably deleterious. Good activity was generally retained by forming esters of a butan-2-ol side chain.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>722734</pmid><doi>10.1021/jm00210a016</doi><tpages>5</tpages></addata></record> |
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language | eng |
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source | ACS Publications; MEDLINE |
subjects | Animals Anti-Inflammatory Agents - chemical synthesis Female Gossypium Granuloma - etiology Granuloma - physiopathology Naphthalenes - chemical synthesis Naphthalenes - pharmacology Rats Structure-Activity Relationship |
title | 4-(6-Methoxy-2-naphthyl)butan-2-one and related analogs, a novel structural class of antiinflammatory compounds |
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