Synthesis and anti-inflammatory activities of some N-[Pyridyl(phenyl)carbonylamino]-tert-butyl/phenyl-1,2,3,6-tetrahydropyridines
Nucleophilic attack of tert-butyl/phenylpyridines 3 on 1-chloro-2,4-dinitrobenzene 4 results in the formation of tert-butyl/phenyl substituted 2,4-dinitrophenylpyridinium chlorides 5. Benzoyl hydrazide and pyridyl acid hydrazides 6 were reacted with the pyridinium chlorides 5 furnishing the 2,4-dini...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1991-03, Vol.39 (3), p.786-791 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | REDDA, K. K RAO, K. N HEIMAN, A. S ONAYEMI, F. Y CLARK, J. B |
| description | Nucleophilic attack of tert-butyl/phenylpyridines 3 on 1-chloro-2,4-dinitrobenzene 4 results in the formation of tert-butyl/phenyl substituted 2,4-dinitrophenylpyridinium chlorides 5. Benzoyl hydrazide and pyridyl acid hydrazides 6 were reacted with the pyridinium chlorides 5 furnishing the 2,4-dinitroanilino derivatives 7, which were subsequently hydrolyzed with water: p-dioxane to yield N-[pyridyl(phenyl)carbonylimino]-tert-butyl/phenylpyridinium ylides 8. The title compounds 9, N-[pyridyl(phenyl)carbonylamino]-tert-butyl/phenyl-1,2,3,6- tetrahydropyridines, were obtained by sodium borohydride reduction of the pyridinium ylides 8. The anti-inflammatory activities of compounds 9a-p were determined using the carrageenan-soaked sponge model of inflammation in Sprague Dawley rats. All compounds tested showed moderate to good anti-inflammatory effects compared to indomethacin. Compounds 9b, 9c and 9p were the most active analogs of the group in this model. |
| doi_str_mv | 10.1248/cpb.39.786 |
| format | Article |
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K ; RAO, K. N ; HEIMAN, A. S ; ONAYEMI, F. Y ; CLARK, J. B</creator><creatorcontrib>REDDA, K. K ; RAO, K. N ; HEIMAN, A. S ; ONAYEMI, F. Y ; CLARK, J. B</creatorcontrib><description>Nucleophilic attack of tert-butyl/phenylpyridines 3 on 1-chloro-2,4-dinitrobenzene 4 results in the formation of tert-butyl/phenyl substituted 2,4-dinitrophenylpyridinium chlorides 5. Benzoyl hydrazide and pyridyl acid hydrazides 6 were reacted with the pyridinium chlorides 5 furnishing the 2,4-dinitroanilino derivatives 7, which were subsequently hydrolyzed with water: p-dioxane to yield N-[pyridyl(phenyl)carbonylimino]-tert-butyl/phenylpyridinium ylides 8. The title compounds 9, N-[pyridyl(phenyl)carbonylamino]-tert-butyl/phenyl-1,2,3,6- tetrahydropyridines, were obtained by sodium borohydride reduction of the pyridinium ylides 8. The anti-inflammatory activities of compounds 9a-p were determined using the carrageenan-soaked sponge model of inflammation in Sprague Dawley rats. All compounds tested showed moderate to good anti-inflammatory effects compared to indomethacin. 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K</creatorcontrib><creatorcontrib>RAO, K. N</creatorcontrib><creatorcontrib>HEIMAN, A. S</creatorcontrib><creatorcontrib>ONAYEMI, F. Y</creatorcontrib><creatorcontrib>CLARK, J. B</creatorcontrib><title>Synthesis and anti-inflammatory activities of some N-[Pyridyl(phenyl)carbonylamino]-tert-butyl/phenyl-1,2,3,6-tetrahydropyridines</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem Pharm Bull (Tokyo)</addtitle><description>Nucleophilic attack of tert-butyl/phenylpyridines 3 on 1-chloro-2,4-dinitrobenzene 4 results in the formation of tert-butyl/phenyl substituted 2,4-dinitrophenylpyridinium chlorides 5. Benzoyl hydrazide and pyridyl acid hydrazides 6 were reacted with the pyridinium chlorides 5 furnishing the 2,4-dinitroanilino derivatives 7, which were subsequently hydrolyzed with water: p-dioxane to yield N-[pyridyl(phenyl)carbonylimino]-tert-butyl/phenylpyridinium ylides 8. The title compounds 9, N-[pyridyl(phenyl)carbonylamino]-tert-butyl/phenyl-1,2,3,6- tetrahydropyridines, were obtained by sodium borohydride reduction of the pyridinium ylides 8. The anti-inflammatory activities of compounds 9a-p were determined using the carrageenan-soaked sponge model of inflammation in Sprague Dawley rats. All compounds tested showed moderate to good anti-inflammatory effects compared to indomethacin. Compounds 9b, 9c and 9p were the most active analogs of the group in this model.</description><subject>Animals</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Pyridines - chemical synthesis</subject><subject>Pyridines - pharmacology</subject><subject>Rats</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1991</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kEtLAzEQgIMoWqsX78JeFIWm5rG7SY4ivkBUUE8iZZJNaGRfJqmwR_-5Ky0ehhn4Pr7DIHREyZyyXF6YXs-5mgtZbqEJ5bnABWN8G00IIQozXvI9tB_jJyGsIILvol1GBMnLYoJ-XoY2LW30MYO2Gid57FtXQ9NA6sKQgUn-2ydvY9a5LHaNzR7x-_MQfDXUZ_3StkN9biDobjyg8W33gZMNCetVGuqLtYDpjM34rBxJCrAcqtD1fwXf2niAdhzU0R5u9hS93Vy_Xt3hh6fb-6vLB9zTgiYsJJNE00qVoIBoyZzIqeIq1zI3ORSkBO40Z0TmSlNrNBdOCiVdxUAYcHyKTtfdPnRfKxvTovHR2LqG1naruJCklIRIOorHG3GlG1st-uAbCMNi87ORn2w4RAO1C9AaH_81qoQq1Nj5BSVHfJM</recordid><startdate>199103</startdate><enddate>199103</enddate><creator>REDDA, K. 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B</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p151t-78280b1d96a9a0b82f7419394b84c4a506a3fb320849b1ecb37f8798fd2a7caf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1991</creationdate><topic>Animals</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Pyridines - chemical synthesis</topic><topic>Pyridines - pharmacology</topic><topic>Rats</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>REDDA, K. K</creatorcontrib><creatorcontrib>RAO, K. N</creatorcontrib><creatorcontrib>HEIMAN, A. S</creatorcontrib><creatorcontrib>ONAYEMI, F. Y</creatorcontrib><creatorcontrib>CLARK, J. B</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>MEDLINE - Academic</collection><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>REDDA, K. K</au><au>RAO, K. N</au><au>HEIMAN, A. S</au><au>ONAYEMI, F. Y</au><au>CLARK, J. B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and anti-inflammatory activities of some N-[Pyridyl(phenyl)carbonylamino]-tert-butyl/phenyl-1,2,3,6-tetrahydropyridines</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem Pharm Bull (Tokyo)</addtitle><date>1991-03</date><risdate>1991</risdate><volume>39</volume><issue>3</issue><spage>786</spage><epage>791</epage><pages>786-791</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Nucleophilic attack of tert-butyl/phenylpyridines 3 on 1-chloro-2,4-dinitrobenzene 4 results in the formation of tert-butyl/phenyl substituted 2,4-dinitrophenylpyridinium chlorides 5. Benzoyl hydrazide and pyridyl acid hydrazides 6 were reacted with the pyridinium chlorides 5 furnishing the 2,4-dinitroanilino derivatives 7, which were subsequently hydrolyzed with water: p-dioxane to yield N-[pyridyl(phenyl)carbonylimino]-tert-butyl/phenylpyridinium ylides 8. The title compounds 9, N-[pyridyl(phenyl)carbonylamino]-tert-butyl/phenyl-1,2,3,6- tetrahydropyridines, were obtained by sodium borohydride reduction of the pyridinium ylides 8. The anti-inflammatory activities of compounds 9a-p were determined using the carrageenan-soaked sponge model of inflammation in Sprague Dawley rats. All compounds tested showed moderate to good anti-inflammatory effects compared to indomethacin. Compounds 9b, 9c and 9p were the most active analogs of the group in this model.</abstract><cop>Tokyo</cop><pub>Maruzen</pub><pmid>2070465</pmid><doi>10.1248/cpb.39.786</doi><tpages>6</tpages></addata></record> |
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| ispartof | Chemical & pharmaceutical bulletin, 1991-03, Vol.39 (3), p.786-791 |
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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, Non-Steroidal - chemical synthesis Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Organic chemistry Preparations and properties Pyridines - chemical synthesis Pyridines - pharmacology Rats |
| title | Synthesis and anti-inflammatory activities of some N-[Pyridyl(phenyl)carbonylamino]-tert-butyl/phenyl-1,2,3,6-tetrahydropyridines |
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