Studies on the Synthesis and Anti-Inflammatory Activity of 2, 6-Di-tert-butylphenols with a Heterocyclic Group at the 4-Position. II
2, 6-Di-tert-butylphenols with an imidazo [2, 1-b] thiazole or 2, 3-dihydroimidazo [2, 1-b] thiazole group at the 4-position were prepared. Substituents were introduced at the 5-position of 6-(3, 5-ditert-butyl-4-hydroxyphenyl)-2, 3-dihydroimidazo [2, 1-b] thiazole (Ia) by means of the Vilsmeier rea...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1983/09/25, Vol.31(9), pp.3179-3185 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | ISOMURA, YASUO ITO, NORIKI SAKAMOTO, SHUICHI HOMMA, HIROSHIGE ABE, TETSUSHI KUBO, KAZUO |
| description | 2, 6-Di-tert-butylphenols with an imidazo [2, 1-b] thiazole or 2, 3-dihydroimidazo [2, 1-b] thiazole group at the 4-position were prepared. Substituents were introduced at the 5-position of 6-(3, 5-ditert-butyl-4-hydroxyphenyl)-2, 3-dihydroimidazo [2, 1-b] thiazole (Ia) by means of the Vilsmeier reaction and Mannich reaction. 6-(3, 5-Di-tert-butyl-4-hydroxyphenyl)-2, 3-dihydroimidazo [2, 1-b] thiazole 1-oxide (IVa) and the 1, 1-dioxide (IVb) were obtained by oxidation of Ia. The above compounds were examined for anti-inflammatory activity in adjuvant-induced arthritis in rats, and some compounds were further tested for activity in the carrageenin-induced rat paw edema assay and in the AcOH-induced writhing assay in mice. Some of the compounds showed potent anti-inflammatory and analgesic activities. The most potent compound, IVa (25 mg/kg, p. o.), had about the same anti-inflammatory activity as indomethacin (2 mg/kg, p. o.), but IVa (50 mg/kg, p. o.) had weaker analgesic activity than aminopyrine (50 mg/kg, p. o.). |
| doi_str_mv | 10.1248/cpb.31.3179 |
| format | Article |
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II</title><source>J-STAGE Free</source><source>MEDLINE</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>Free Full-Text Journals in Chemistry</source><creator>ISOMURA, YASUO ; ITO, NORIKI ; SAKAMOTO, SHUICHI ; HOMMA, HIROSHIGE ; ABE, TETSUSHI ; KUBO, KAZUO</creator><creatorcontrib>ISOMURA, YASUO ; ITO, NORIKI ; SAKAMOTO, SHUICHI ; HOMMA, HIROSHIGE ; ABE, TETSUSHI ; KUBO, KAZUO</creatorcontrib><description>2, 6-Di-tert-butylphenols with an imidazo [2, 1-b] thiazole or 2, 3-dihydroimidazo [2, 1-b] thiazole group at the 4-position were prepared. Substituents were introduced at the 5-position of 6-(3, 5-ditert-butyl-4-hydroxyphenyl)-2, 3-dihydroimidazo [2, 1-b] thiazole (Ia) by means of the Vilsmeier reaction and Mannich reaction. 6-(3, 5-Di-tert-butyl-4-hydroxyphenyl)-2, 3-dihydroimidazo [2, 1-b] thiazole 1-oxide (IVa) and the 1, 1-dioxide (IVb) were obtained by oxidation of Ia. The above compounds were examined for anti-inflammatory activity in adjuvant-induced arthritis in rats, and some compounds were further tested for activity in the carrageenin-induced rat paw edema assay and in the AcOH-induced writhing assay in mice. Some of the compounds showed potent anti-inflammatory and analgesic activities. 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II</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>2, 6-Di-tert-butylphenols with an imidazo [2, 1-b] thiazole or 2, 3-dihydroimidazo [2, 1-b] thiazole group at the 4-position were prepared. Substituents were introduced at the 5-position of 6-(3, 5-ditert-butyl-4-hydroxyphenyl)-2, 3-dihydroimidazo [2, 1-b] thiazole (Ia) by means of the Vilsmeier reaction and Mannich reaction. 6-(3, 5-Di-tert-butyl-4-hydroxyphenyl)-2, 3-dihydroimidazo [2, 1-b] thiazole 1-oxide (IVa) and the 1, 1-dioxide (IVb) were obtained by oxidation of Ia. The above compounds were examined for anti-inflammatory activity in adjuvant-induced arthritis in rats, and some compounds were further tested for activity in the carrageenin-induced rat paw edema assay and in the AcOH-induced writhing assay in mice. Some of the compounds showed potent anti-inflammatory and analgesic activities. The most potent compound, IVa (25 mg/kg, p. o.), had about the same anti-inflammatory activity as indomethacin (2 mg/kg, p. o.), but IVa (50 mg/kg, p. o.) had weaker analgesic activity than aminopyrine (50 mg/kg, p. o.).</description><subject>Animals</subject><subject>Anti-Inflammatory Agents - chemical synthesis</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis</subject><subject>Arthritis, Experimental - drug therapy</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Mannich reaction</subject><subject>Mice</subject><subject>Organic chemistry</subject><subject>Phenols - chemical synthesis</subject><subject>Phenols - pharmacology</subject><subject>Preparations and properties</subject><subject>Rats</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1983</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkEtv1DAURiMEKkNhxRrJC8QGPPiR8WM5aqEdqRJIhXV049iMq8QebKcoe344CTMMkuW7OEf3u_qq6jUla8pq9dEc2jWn85P6SbWivJZ4wxh_Wq0IIRozLvjz6kXOD4SwDZH8oroQgkip2Kr6fV_GztuMYkBlb9H9FOaRfUYQOrQNxeNdcD0MA5SYJrQ1xT_6MqHoEPuABL72uNhUcDuWqT_sbYh9Rr982SNAt3ZG0Uym9wbdpDgeEJS_MTX-GrMvPoY12u1eVs8c9Nm-Os3L6vvnT9-ubvHdl5vd1fYOm5pRjZUjrQbBOHBGQLWC6w6cE9BJVVPHRCesk4IqIVSnqSHaACEAhArltKv5ZfXuuPeQ4s_R5tIMPhvb9xBsHHOjiBKaMDmL74-iSTHnZF1zSH6ANDWUNEvnzdx5w2mzdD7bb05rx3aw3dk9lTzztycO2UDvEgTj81nTXEoil-uuj9pDLvDDnjmk4k1vl0iqN2qJ1f8-qf_jPaTGBv4HwPmhUg</recordid><startdate>1983</startdate><enddate>1983</enddate><creator>ISOMURA, YASUO</creator><creator>ITO, NORIKI</creator><creator>SAKAMOTO, SHUICHI</creator><creator>HOMMA, HIROSHIGE</creator><creator>ABE, TETSUSHI</creator><creator>KUBO, KAZUO</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</general><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><scope>7X8</scope></search><sort><creationdate>1983</creationdate><title>Studies on the Synthesis and Anti-Inflammatory Activity of 2, 6-Di-tert-butylphenols with a Heterocyclic Group at the 4-Position. II</title><author>ISOMURA, YASUO ; ITO, NORIKI ; SAKAMOTO, SHUICHI ; HOMMA, HIROSHIGE ; ABE, TETSUSHI ; KUBO, KAZUO</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4219-8f0b9a623a320a8b639daff6ad7841f26d6ef7618668d91c09ca00aa0168f9f43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1983</creationdate><topic>Animals</topic><topic>Anti-Inflammatory Agents - chemical synthesis</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis</topic><topic>Arthritis, Experimental - drug therapy</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Mannich reaction</topic><topic>Mice</topic><topic>Organic chemistry</topic><topic>Phenols - chemical synthesis</topic><topic>Phenols - pharmacology</topic><topic>Preparations and properties</topic><topic>Rats</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>ISOMURA, YASUO</creatorcontrib><creatorcontrib>ITO, NORIKI</creatorcontrib><creatorcontrib>SAKAMOTO, SHUICHI</creatorcontrib><creatorcontrib>HOMMA, HIROSHIGE</creatorcontrib><creatorcontrib>ABE, TETSUSHI</creatorcontrib><creatorcontrib>KUBO, KAZUO</creatorcontrib><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><collection>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>ISOMURA, YASUO</au><au>ITO, NORIKI</au><au>SAKAMOTO, SHUICHI</au><au>HOMMA, HIROSHIGE</au><au>ABE, TETSUSHI</au><au>KUBO, KAZUO</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Studies on the Synthesis and Anti-Inflammatory Activity of 2, 6-Di-tert-butylphenols with a Heterocyclic Group at the 4-Position. II</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1983</date><risdate>1983</risdate><volume>31</volume><issue>9</issue><spage>3179</spage><epage>3185</epage><pages>3179-3185</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>2, 6-Di-tert-butylphenols with an imidazo [2, 1-b] thiazole or 2, 3-dihydroimidazo [2, 1-b] thiazole group at the 4-position were prepared. Substituents were introduced at the 5-position of 6-(3, 5-ditert-butyl-4-hydroxyphenyl)-2, 3-dihydroimidazo [2, 1-b] thiazole (Ia) by means of the Vilsmeier reaction and Mannich reaction. 6-(3, 5-Di-tert-butyl-4-hydroxyphenyl)-2, 3-dihydroimidazo [2, 1-b] thiazole 1-oxide (IVa) and the 1, 1-dioxide (IVb) were obtained by oxidation of Ia. The above compounds were examined for anti-inflammatory activity in adjuvant-induced arthritis in rats, and some compounds were further tested for activity in the carrageenin-induced rat paw edema assay and in the AcOH-induced writhing assay in mice. Some of the compounds showed potent anti-inflammatory and analgesic activities. The most potent compound, IVa (25 mg/kg, p. o.), had about the same anti-inflammatory activity as indomethacin (2 mg/kg, p. o.), but IVa (50 mg/kg, p. o.) had weaker analgesic activity than aminopyrine (50 mg/kg, p. o.).</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>6607782</pmid><doi>10.1248/cpb.31.3179</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| source | J-STAGE Free; MEDLINE; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
| subjects | Animals Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis Arthritis, Experimental - drug therapy Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Mannich reaction Mice Organic chemistry Phenols - chemical synthesis Phenols - pharmacology Preparations and properties Rats |
| title | Studies on the Synthesis and Anti-Inflammatory Activity of 2, 6-Di-tert-butylphenols with a Heterocyclic Group at the 4-Position. II |
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