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...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of medicinal chemistry 1978-12, Vol.21 (12), p.1260-1264
Hauptverfasser: Goudie, Alexander C, Gaster, Laramie M, Lake, Antony W, Rose, Carl J, Freeman, Patricia C, Hughes, Bryn O, Miller, David
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1264
container_issue 12
container_start_page 1260
container_title Journal of medicinal chemistry
container_volume 21
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
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_74261559</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>74261559</sourcerecordid><originalsourceid>FETCH-LOGICAL-a334t-918a1cb62786d28ecf5ed4e94e44a8ce0e575913aebdc57e6109ad0dfa73c8df3</originalsourceid><addsrcrecordid>eNptkEtv1DAUhS3Eayis2LLIiofA4FfiZFlV0FYqBcQg2Fl37BsmgxNPbQd1_j1GqSoWrM7VOZ_OlQ4hTzl7y5ng73YjK8KA8eYOWfFaMKpapu6SVfEFFY2QD8mjlHaMMcmFfEDuayG0VCsSFH3Z0I-Yt-H6QAWdYL_N24N_tZkzTMUIE1YwuSqih4yu3ODDz_SmgmoKv9FXKcfZ5jmCr6yHlKrQFygPw9R7GEfIIR4qG8Z9mCeXHpN7PfiET270iHz78H59ckYvPp2enxxfUJBSZdrxFrjdNEK3jRMt2r5Gp7BTqBS0FhnWuu64BNw4W2tsOOvAMdeDlrZ1vTwiz5fefQxXM6ZsxiFZ9B4mDHMyWomG13VXwNcLaGNIKWJv9nEYIR4MZ-bvuuafdQv97KZ23ozobtllzhLTJR5SxuvbFOIv02ipa7P-_NX8uFzzL9_bS3Na-BcLDzaZXZhjGTf99_EfwgGRnQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>74261559</pqid></control><display><type>article</type><title>4-(6-Methoxy-2-naphthyl)butan-2-one and related analogs, a novel structural class of antiinflammatory compounds</title><source>ACS Publications</source><source>MEDLINE</source><creator>Goudie, Alexander C ; Gaster, Laramie M ; Lake, Antony W ; Rose, Carl J ; Freeman, Patricia C ; Hughes, Bryn O ; Miller, David</creator><creatorcontrib>Goudie, Alexander C ; Gaster, Laramie M ; Lake, Antony W ; Rose, Carl J ; Freeman, Patricia C ; Hughes, Bryn O ; Miller, David</creatorcontrib><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.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00210a016</identifier><identifier>PMID: 722734</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Animals ; Anti-Inflammatory Agents - chemical synthesis ; Female ; Gossypium ; Granuloma - etiology ; Granuloma - physiopathology ; Naphthalenes - chemical synthesis ; Naphthalenes - pharmacology ; Rats ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 1978-12, Vol.21 (12), p.1260-1264</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a334t-918a1cb62786d28ecf5ed4e94e44a8ce0e575913aebdc57e6109ad0dfa73c8df3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm00210a016$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00210a016$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,782,786,2769,27085,27933,27934,56747,56797</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/722734$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><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><title>4-(6-Methoxy-2-naphthyl)butan-2-one and related analogs, a novel structural class of antiinflammatory compounds</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><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.</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>
fulltext fulltext
identifier ISSN: 0022-2623
ispartof Journal of medicinal chemistry, 1978-12, Vol.21 (12), p.1260-1264
issn 0022-2623
1520-4804
language eng
recordid cdi_proquest_miscellaneous_74261559
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
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-11-30T02%3A50%3A24IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=4-(6-Methoxy-2-naphthyl)butan-2-one%20and%20related%20analogs,%20a%20novel%20structural%20class%20of%20antiinflammatory%20compounds&rft.jtitle=Journal%20of%20medicinal%20chemistry&rft.au=Goudie,%20Alexander%20C&rft.date=1978-12&rft.volume=21&rft.issue=12&rft.spage=1260&rft.epage=1264&rft.pages=1260-1264&rft.issn=0022-2623&rft.eissn=1520-4804&rft_id=info:doi/10.1021/jm00210a016&rft_dat=%3Cproquest_cross%3E74261559%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=74261559&rft_id=info:pmid/722734&rfr_iscdi=true