Potential Antiinflammatory Agents. II. Synthesis and Structure-Activity Relationships of 6-Chloro-5-cyclohexylindan-1-carboxylic Acid (TAI-284) and Related 5-Substituted Indan-1-carboxylic Acids
6-Chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284) and related 5-substituted indan-1-carboxylic acids were prepared for the evaluation of antiinflammatory action. Among them, TAI-284 showed the most potent activity, comparable to that of indomethacin. The replacement of the cyclohexyl moiety at...
Gespeichert in:
| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1974/03/25, Vol.22(3), pp.529-536 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 536 |
|---|---|
| container_issue | 3 |
| container_start_page | 529 |
| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 22 |
| creator | NOGUCHI, SHUNSAKU KISHIMOTO, SHOJI MINAMIDA, ISAO OBAYASHI, MIKIHIKO |
| description | 6-Chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284) and related 5-substituted indan-1-carboxylic acids were prepared for the evaluation of antiinflammatory action. Among them, TAI-284 showed the most potent activity, comparable to that of indomethacin. The replacement of the cyclohexyl moiety at C-5 by other alkyl groups such as isobutyl or isopropyl, or the removal of the chlorine atom at C-6 resulted in a considerable reduction of the activities. The resolution of TAI-284 was effected with quinine, and it was found that the antiinflammatory activity virtually resided in the dextro isomer, the absolute configuration of which was assigned the sinister series by the optical rotatory dispersion spectrum and X-ray crystarography. |
| doi_str_mv | 10.1248/cpb.22.529 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_1459781663</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3131742521</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4889-716c6e105885bb1b3bb31eb3c1be9ceca3bbcb9c2d4db7eae3a65950ecd81bc83</originalsourceid><addsrcrecordid>eNptkU-L1DAYxoMo67h68S4EvKiQmj9Nmx7L4J_CguKs55Kk72wzdJoxSRf79fxktjvDevGSlze_J78cHoReM5oxnquP9mQyzjPJqydow0ReEsm5eIo2lNKKcFGI5-hFjAdKuaSluEJXec55QasN-vPdJxiT0wOul-HG_aCPR518mHF9t5CY4abJ8G4eUw_RRazHDu9SmGyaApDaJnfv0ox_wKCT82Ps3Sliv8cF2faDD55IYmc7-B5-z4MbOz0SRqwOxq-7xbV1HX53WzeEq_z9g_7BBR2WZDeZmFya1q35_9v4Ej3b6yHCq8u8Rj8_f7rdfiU337402_qG2FypipSssAUwKpWSxjAjjBEMjLDMQGXB6uXCmsryLu9MCRqELmQlKdhOMWOVuEZvz95T8L8miKk9-CmMy5cty2VVKlYUYkl9OKds8DEG2Len4I46zC2j7dpWu7TVct4ubS3hNxflZI7QPUYv9Sx8e-aHmPQdPHIdkrMDrCpWSbXqxPlYrP9or0MLo_gLCfCqhQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1459781663</pqid></control><display><type>article</type><title>Potential Antiinflammatory Agents. II. Synthesis and Structure-Activity Relationships of 6-Chloro-5-cyclohexylindan-1-carboxylic Acid (TAI-284) and Related 5-Substituted Indan-1-carboxylic Acids</title><source>J-STAGE Free</source><source>MEDLINE</source><source>EZB-FREE-00999 freely available EZB journals</source><source>Free Full-Text Journals in Chemistry</source><creator>NOGUCHI, SHUNSAKU ; KISHIMOTO, SHOJI ; MINAMIDA, ISAO ; OBAYASHI, MIKIHIKO</creator><creatorcontrib>NOGUCHI, SHUNSAKU ; KISHIMOTO, SHOJI ; MINAMIDA, ISAO ; OBAYASHI, MIKIHIKO</creatorcontrib><description>6-Chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284) and related 5-substituted indan-1-carboxylic acids were prepared for the evaluation of antiinflammatory action. Among them, TAI-284 showed the most potent activity, comparable to that of indomethacin. The replacement of the cyclohexyl moiety at C-5 by other alkyl groups such as isobutyl or isopropyl, or the removal of the chlorine atom at C-6 resulted in a considerable reduction of the activities. The resolution of TAI-284 was effected with quinine, and it was found that the antiinflammatory activity virtually resided in the dextro isomer, the absolute configuration of which was assigned the sinister series by the optical rotatory dispersion spectrum and X-ray crystarography.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.22.529</identifier><identifier>PMID: 4422609</identifier><language>eng</language><publisher>Japan: The Pharmaceutical Society of Japan</publisher><subject>Animals ; Anti-Inflammatory Agents - chemical synthesis ; Anti-Inflammatory Agents - therapeutic use ; Anti-Inflammatory Agents - toxicity ; Carboxylic Acids - chemical synthesis ; Carboxylic Acids - therapeutic use ; Carboxylic Acids - toxicity ; Cyclohexanes - analogs & derivatives ; Cyclohexanes - chemical synthesis ; Cyclohexanes - therapeutic use ; Cyclohexanes - toxicity ; Edema - drug therapy ; Indenes - chemical synthesis ; Indenes - therapeutic use ; Indenes - toxicity ; Lethal Dose 50 ; Rats ; Stereoisomerism ; Structure-Activity Relationship</subject><ispartof>Chemical and Pharmaceutical Bulletin, 1974/03/25, Vol.22(3), pp.529-536</ispartof><rights>The Pharmaceutical Society of Japan</rights><rights>Copyright Japan Science and Technology Agency 1974</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4889-716c6e105885bb1b3bb31eb3c1be9ceca3bbcb9c2d4db7eae3a65950ecd81bc83</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1876,4009,27902,27903,27904</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/4422609$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>NOGUCHI, SHUNSAKU</creatorcontrib><creatorcontrib>KISHIMOTO, SHOJI</creatorcontrib><creatorcontrib>MINAMIDA, ISAO</creatorcontrib><creatorcontrib>OBAYASHI, MIKIHIKO</creatorcontrib><title>Potential Antiinflammatory Agents. II. Synthesis and Structure-Activity Relationships of 6-Chloro-5-cyclohexylindan-1-carboxylic Acid (TAI-284) and Related 5-Substituted Indan-1-carboxylic Acids</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>6-Chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284) and related 5-substituted indan-1-carboxylic acids were prepared for the evaluation of antiinflammatory action. Among them, TAI-284 showed the most potent activity, comparable to that of indomethacin. The replacement of the cyclohexyl moiety at C-5 by other alkyl groups such as isobutyl or isopropyl, or the removal of the chlorine atom at C-6 resulted in a considerable reduction of the activities. The resolution of TAI-284 was effected with quinine, and it was found that the antiinflammatory activity virtually resided in the dextro isomer, the absolute configuration of which was assigned the sinister series by the optical rotatory dispersion spectrum and X-ray crystarography.</description><subject>Animals</subject><subject>Anti-Inflammatory Agents - chemical synthesis</subject><subject>Anti-Inflammatory Agents - therapeutic use</subject><subject>Anti-Inflammatory Agents - toxicity</subject><subject>Carboxylic Acids - chemical synthesis</subject><subject>Carboxylic Acids - therapeutic use</subject><subject>Carboxylic Acids - toxicity</subject><subject>Cyclohexanes - analogs & derivatives</subject><subject>Cyclohexanes - chemical synthesis</subject><subject>Cyclohexanes - therapeutic use</subject><subject>Cyclohexanes - toxicity</subject><subject>Edema - drug therapy</subject><subject>Indenes - chemical synthesis</subject><subject>Indenes - therapeutic use</subject><subject>Indenes - toxicity</subject><subject>Lethal Dose 50</subject><subject>Rats</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1974</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkU-L1DAYxoMo67h68S4EvKiQmj9Nmx7L4J_CguKs55Kk72wzdJoxSRf79fxktjvDevGSlze_J78cHoReM5oxnquP9mQyzjPJqydow0ReEsm5eIo2lNKKcFGI5-hFjAdKuaSluEJXec55QasN-vPdJxiT0wOul-HG_aCPR518mHF9t5CY4abJ8G4eUw_RRazHDu9SmGyaApDaJnfv0ox_wKCT82Ps3Sliv8cF2faDD55IYmc7-B5-z4MbOz0SRqwOxq-7xbV1HX53WzeEq_z9g_7BBR2WZDeZmFya1q35_9v4Ej3b6yHCq8u8Rj8_f7rdfiU337402_qG2FypipSssAUwKpWSxjAjjBEMjLDMQGXB6uXCmsryLu9MCRqELmQlKdhOMWOVuEZvz95T8L8miKk9-CmMy5cty2VVKlYUYkl9OKds8DEG2Len4I46zC2j7dpWu7TVct4ubS3hNxflZI7QPUYv9Sx8e-aHmPQdPHIdkrMDrCpWSbXqxPlYrP9or0MLo_gLCfCqhQ</recordid><startdate>1974</startdate><enddate>1974</enddate><creator>NOGUCHI, SHUNSAKU</creator><creator>KISHIMOTO, SHOJI</creator><creator>MINAMIDA, ISAO</creator><creator>OBAYASHI, MIKIHIKO</creator><general>The 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></search><sort><creationdate>1974</creationdate><title>Potential Antiinflammatory Agents. II. Synthesis and Structure-Activity Relationships of 6-Chloro-5-cyclohexylindan-1-carboxylic Acid (TAI-284) and Related 5-Substituted Indan-1-carboxylic Acids</title><author>NOGUCHI, SHUNSAKU ; KISHIMOTO, SHOJI ; MINAMIDA, ISAO ; OBAYASHI, MIKIHIKO</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4889-716c6e105885bb1b3bb31eb3c1be9ceca3bbcb9c2d4db7eae3a65950ecd81bc83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1974</creationdate><topic>Animals</topic><topic>Anti-Inflammatory Agents - chemical synthesis</topic><topic>Anti-Inflammatory Agents - therapeutic use</topic><topic>Anti-Inflammatory Agents - toxicity</topic><topic>Carboxylic Acids - chemical synthesis</topic><topic>Carboxylic Acids - therapeutic use</topic><topic>Carboxylic Acids - toxicity</topic><topic>Cyclohexanes - analogs & derivatives</topic><topic>Cyclohexanes - chemical synthesis</topic><topic>Cyclohexanes - therapeutic use</topic><topic>Cyclohexanes - toxicity</topic><topic>Edema - drug therapy</topic><topic>Indenes - chemical synthesis</topic><topic>Indenes - therapeutic use</topic><topic>Indenes - toxicity</topic><topic>Lethal Dose 50</topic><topic>Rats</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>NOGUCHI, SHUNSAKU</creatorcontrib><creatorcontrib>KISHIMOTO, SHOJI</creatorcontrib><creatorcontrib>MINAMIDA, ISAO</creatorcontrib><creatorcontrib>OBAYASHI, MIKIHIKO</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><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>NOGUCHI, SHUNSAKU</au><au>KISHIMOTO, SHOJI</au><au>MINAMIDA, ISAO</au><au>OBAYASHI, MIKIHIKO</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Potential Antiinflammatory Agents. II. Synthesis and Structure-Activity Relationships of 6-Chloro-5-cyclohexylindan-1-carboxylic Acid (TAI-284) and Related 5-Substituted Indan-1-carboxylic Acids</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1974</date><risdate>1974</risdate><volume>22</volume><issue>3</issue><spage>529</spage><epage>536</epage><pages>529-536</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>6-Chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284) and related 5-substituted indan-1-carboxylic acids were prepared for the evaluation of antiinflammatory action. Among them, TAI-284 showed the most potent activity, comparable to that of indomethacin. The replacement of the cyclohexyl moiety at C-5 by other alkyl groups such as isobutyl or isopropyl, or the removal of the chlorine atom at C-6 resulted in a considerable reduction of the activities. The resolution of TAI-284 was effected with quinine, and it was found that the antiinflammatory activity virtually resided in the dextro isomer, the absolute configuration of which was assigned the sinister series by the optical rotatory dispersion spectrum and X-ray crystarography.</abstract><cop>Japan</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>4422609</pmid><doi>10.1248/cpb.22.529</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1974/03/25, Vol.22(3), pp.529-536 |
| issn | 0009-2363 1347-5223 |
| language | eng |
| recordid | cdi_proquest_journals_1459781663 |
| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Animals Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents - therapeutic use Anti-Inflammatory Agents - toxicity Carboxylic Acids - chemical synthesis Carboxylic Acids - therapeutic use Carboxylic Acids - toxicity Cyclohexanes - analogs & derivatives Cyclohexanes - chemical synthesis Cyclohexanes - therapeutic use Cyclohexanes - toxicity Edema - drug therapy Indenes - chemical synthesis Indenes - therapeutic use Indenes - toxicity Lethal Dose 50 Rats Stereoisomerism Structure-Activity Relationship |
| title | Potential Antiinflammatory Agents. II. Synthesis and Structure-Activity Relationships of 6-Chloro-5-cyclohexylindan-1-carboxylic Acid (TAI-284) and Related 5-Substituted Indan-1-carboxylic Acids |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-22T21%3A46%3A41IST&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=Potential%20Antiinflammatory%20Agents.%20II.%20Synthesis%20and%20Structure-Activity%20Relationships%20of%206-Chloro-5-cyclohexylindan-1-carboxylic%20Acid%20(TAI-284)%20and%20Related%205-Substituted%20Indan-1-carboxylic%20Acids&rft.jtitle=Chemical%20&%20pharmaceutical%20bulletin&rft.au=NOGUCHI,%20SHUNSAKU&rft.date=1974&rft.volume=22&rft.issue=3&rft.spage=529&rft.epage=536&rft.pages=529-536&rft.issn=0009-2363&rft.eissn=1347-5223&rft_id=info:doi/10.1248/cpb.22.529&rft_dat=%3Cproquest_cross%3E3131742521%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=1459781663&rft_id=info:pmid/4422609&rfr_iscdi=true |