Synthesis and calcium antagonistic activity of 2,6,6-trimethyl-3-carbomethoxy(ethoxy)-4-aryl-1,4,5,6,7,8-hexahydroquinoline derivatives
Twelve new 2,6,6-trimethyl-3-carbomethoxy(ethoxy)-4-aryl-1,4,5,6,7,8-hexahydroquinoline derivatives have been prepared. Their structures were confirmed by IR, 1H NMR, mass and elemental analysis. The calcium antagonistic activity of these compounds was tested in rat aortic rings precontracted with 3...
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| Veröffentlicht in: | Farmaco (Società chimica italiana : 1989) 2000-11, Vol.55 (11), p.665-668 |
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| container_title | Farmaco (Società chimica italiana : 1989) |
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| creator | SIMSEK, Rahime ISMAILOGLU, U. Burcin SAFAK, Cihat SAHIN-ERDEMLI, Inci |
| description | Twelve new 2,6,6-trimethyl-3-carbomethoxy(ethoxy)-4-aryl-1,4,5,6,7,8-hexahydroquinoline derivatives have been prepared. Their structures were confirmed by IR,
1H NMR, mass and elemental analysis. The calcium antagonistic activity of these compounds was tested in rat aortic rings precontracted with 30 mM K
+. The compounds
IVa,
IVc,
IVe,
IVf,
IVh–
l induced concentration dependent relaxation response in precontracted aortic rings. The concentrations that cause 50% relaxation of K
+-contraction were also calculated for the compounds
IVe,
IVf,
IVj. According to pharmacological results, compound
IVl exert the most activity and compound
IVc has been found to be least active in this series. The methyl ester derivatives carrying mono halogensubstitutent in the phenyl ring, the activity order is F>Br>Cl. Replacement of the substituted phenyl ring with the pyridine ring increases the activity. |
| doi_str_mv | 10.1016/S0014-827X(00)00086-0 |
| format | Article |
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1H NMR, mass and elemental analysis. The calcium antagonistic activity of these compounds was tested in rat aortic rings precontracted with 30 mM K
+. The compounds
IVa,
IVc,
IVe,
IVf,
IVh–
l induced concentration dependent relaxation response in precontracted aortic rings. The concentrations that cause 50% relaxation of K
+-contraction were also calculated for the compounds
IVe,
IVf,
IVj. According to pharmacological results, compound
IVl exert the most activity and compound
IVc has been found to be least active in this series. The methyl ester derivatives carrying mono halogensubstitutent in the phenyl ring, the activity order is F>Br>Cl. Replacement of the substituted phenyl ring with the pyridine ring increases the activity.</description><identifier>ISSN: 0014-827X</identifier><identifier>EISSN: 1879-0569</identifier><identifier>DOI: 10.1016/S0014-827X(00)00086-0</identifier><identifier>PMID: 11204940</identifier><language>eng</language><publisher>Lausanne: Elsevier SAS</publisher><subject>1,4-Dihydropyridine ; Animals ; Aorta, Thoracic - drug effects ; Biological and medical sciences ; Calcium antagonistic activity ; Calcium Channel Blockers - chemical synthesis ; Calcium Channel Blockers - pharmacology ; Cardiovascular system ; Dihydropyridines - chemical synthesis ; Dihydropyridines - pharmacology ; Hexahydroquinoline ; In Vitro Techniques ; Magnetic Resonance Spectroscopy ; Male ; Mass Spectrometry ; Medical sciences ; Miscellaneous ; Muscle Contraction - drug effects ; Muscle, Smooth, Vascular - drug effects ; Pharmacology ; Pharmacology. Drug treatments ; Quinolines - chemistry ; Quinolines - pharmacology ; Rats ; Spectra ; Spectrophotometry, Infrared ; Spectroscopy, Fourier Transform Infrared</subject><ispartof>Farmaco (Società chimica italiana : 1989), 2000-11, Vol.55 (11), p.665-668</ispartof><rights>2000 Elsevier Science S.A.</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-9ad92308700d6eceb83acdecf7d8a1be1fb1decbbfcee55c0a60e4580e4b567b3</citedby><cites>FETCH-LOGICAL-c389t-9ad92308700d6eceb83acdecf7d8a1be1fb1decbbfcee55c0a60e4580e4b567b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=844159$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11204940$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>SIMSEK, Rahime</creatorcontrib><creatorcontrib>ISMAILOGLU, U. Burcin</creatorcontrib><creatorcontrib>SAFAK, Cihat</creatorcontrib><creatorcontrib>SAHIN-ERDEMLI, Inci</creatorcontrib><title>Synthesis and calcium antagonistic activity of 2,6,6-trimethyl-3-carbomethoxy(ethoxy)-4-aryl-1,4,5,6,7,8-hexahydroquinoline derivatives</title><title>Farmaco (Società chimica italiana : 1989)</title><addtitle>Farmaco</addtitle><description>Twelve new 2,6,6-trimethyl-3-carbomethoxy(ethoxy)-4-aryl-1,4,5,6,7,8-hexahydroquinoline derivatives have been prepared. Their structures were confirmed by IR,
1H NMR, mass and elemental analysis. The calcium antagonistic activity of these compounds was tested in rat aortic rings precontracted with 30 mM K
+. The compounds
IVa,
IVc,
IVe,
IVf,
IVh–
l induced concentration dependent relaxation response in precontracted aortic rings. The concentrations that cause 50% relaxation of K
+-contraction were also calculated for the compounds
IVe,
IVf,
IVj. According to pharmacological results, compound
IVl exert the most activity and compound
IVc has been found to be least active in this series. The methyl ester derivatives carrying mono halogensubstitutent in the phenyl ring, the activity order is F>Br>Cl. Replacement of the substituted phenyl ring with the pyridine ring increases the activity.</description><subject>1,4-Dihydropyridine</subject><subject>Animals</subject><subject>Aorta, Thoracic - drug effects</subject><subject>Biological and medical sciences</subject><subject>Calcium antagonistic activity</subject><subject>Calcium Channel Blockers - chemical synthesis</subject><subject>Calcium Channel Blockers - pharmacology</subject><subject>Cardiovascular system</subject><subject>Dihydropyridines - chemical synthesis</subject><subject>Dihydropyridines - pharmacology</subject><subject>Hexahydroquinoline</subject><subject>In Vitro Techniques</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Male</subject><subject>Mass Spectrometry</subject><subject>Medical sciences</subject><subject>Miscellaneous</subject><subject>Muscle Contraction - drug effects</subject><subject>Muscle, Smooth, Vascular - drug effects</subject><subject>Pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Quinolines - chemistry</subject><subject>Quinolines - pharmacology</subject><subject>Rats</subject><subject>Spectra</subject><subject>Spectrophotometry, Infrared</subject><subject>Spectroscopy, Fourier Transform Infrared</subject><issn>0014-827X</issn><issn>1879-0569</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkV1rFTEQhoMo9lj9CcqCIC1sdLK7-dirIqVVoeBFFbwL-Zj1RPbs1iTn0P0F_m1zeg710ptMXvLMZOYdQl4zeM-AiQ-3AKyjqpE_zgDOAUAJCk_IiinZU-Cif0pWj8gJeZHSryKlFPI5OWGsga7vYEX-3C5TXmMKqTKTr5wZXdhuyj2bn_MUUg6uMi6HXchLNQ9VU4ta0BzDBvN6GWlLnYl23qv5fjk7hHPaURPLK6u7mpcMWSu6xnuzXnycf2_DNI9hwspjDDtTimN6SZ4NZkz46hhPyffrq2-Xn-nN109fLj_eUNeqPtPe-L5pQUkAL9ChVa1xHt0gvTLMIhssK9LawSFy7sAIwI6rclgupG1PybtD3bt9I5iy3oTkcBzNhPM2adnwrmENLyA_gC7OKUUc9F0ZukylGej9BvTDBvTeXg2gHzagoeS9OX6wtRv0_7KOlhfg7REwqdg9RDO5kB451XWM94W6OFBYzNgFjDq5gJNDHyK6rP0c_tPIX-ufpLA</recordid><startdate>20001101</startdate><enddate>20001101</enddate><creator>SIMSEK, Rahime</creator><creator>ISMAILOGLU, U. Burcin</creator><creator>SAFAK, Cihat</creator><creator>SAHIN-ERDEMLI, Inci</creator><general>Elsevier SAS</general><general>Elsevier Science</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>20001101</creationdate><title>Synthesis and calcium antagonistic activity of 2,6,6-trimethyl-3-carbomethoxy(ethoxy)-4-aryl-1,4,5,6,7,8-hexahydroquinoline derivatives</title><author>SIMSEK, Rahime ; ISMAILOGLU, U. Burcin ; SAFAK, Cihat ; SAHIN-ERDEMLI, Inci</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-9ad92308700d6eceb83acdecf7d8a1be1fb1decbbfcee55c0a60e4580e4b567b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>1,4-Dihydropyridine</topic><topic>Animals</topic><topic>Aorta, Thoracic - drug effects</topic><topic>Biological and medical sciences</topic><topic>Calcium antagonistic activity</topic><topic>Calcium Channel Blockers - chemical synthesis</topic><topic>Calcium Channel Blockers - pharmacology</topic><topic>Cardiovascular system</topic><topic>Dihydropyridines - chemical synthesis</topic><topic>Dihydropyridines - pharmacology</topic><topic>Hexahydroquinoline</topic><topic>In Vitro Techniques</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Male</topic><topic>Mass Spectrometry</topic><topic>Medical sciences</topic><topic>Miscellaneous</topic><topic>Muscle Contraction - drug effects</topic><topic>Muscle, Smooth, Vascular - drug effects</topic><topic>Pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Quinolines - chemistry</topic><topic>Quinolines - pharmacology</topic><topic>Rats</topic><topic>Spectra</topic><topic>Spectrophotometry, Infrared</topic><topic>Spectroscopy, Fourier Transform Infrared</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>SIMSEK, Rahime</creatorcontrib><creatorcontrib>ISMAILOGLU, U. Burcin</creatorcontrib><creatorcontrib>SAFAK, Cihat</creatorcontrib><creatorcontrib>SAHIN-ERDEMLI, Inci</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>Farmaco (Società chimica italiana : 1989)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>SIMSEK, Rahime</au><au>ISMAILOGLU, U. Burcin</au><au>SAFAK, Cihat</au><au>SAHIN-ERDEMLI, Inci</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and calcium antagonistic activity of 2,6,6-trimethyl-3-carbomethoxy(ethoxy)-4-aryl-1,4,5,6,7,8-hexahydroquinoline derivatives</atitle><jtitle>Farmaco (Società chimica italiana : 1989)</jtitle><addtitle>Farmaco</addtitle><date>2000-11-01</date><risdate>2000</risdate><volume>55</volume><issue>11</issue><spage>665</spage><epage>668</epage><pages>665-668</pages><issn>0014-827X</issn><eissn>1879-0569</eissn><abstract>Twelve new 2,6,6-trimethyl-3-carbomethoxy(ethoxy)-4-aryl-1,4,5,6,7,8-hexahydroquinoline derivatives have been prepared. Their structures were confirmed by IR,
1H NMR, mass and elemental analysis. The calcium antagonistic activity of these compounds was tested in rat aortic rings precontracted with 30 mM K
+. The compounds
IVa,
IVc,
IVe,
IVf,
IVh–
l induced concentration dependent relaxation response in precontracted aortic rings. The concentrations that cause 50% relaxation of K
+-contraction were also calculated for the compounds
IVe,
IVf,
IVj. According to pharmacological results, compound
IVl exert the most activity and compound
IVc has been found to be least active in this series. The methyl ester derivatives carrying mono halogensubstitutent in the phenyl ring, the activity order is F>Br>Cl. Replacement of the substituted phenyl ring with the pyridine ring increases the activity.</abstract><cop>Lausanne</cop><pub>Elsevier SAS</pub><pmid>11204940</pmid><doi>10.1016/S0014-827X(00)00086-0</doi><tpages>4</tpages></addata></record> |
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| ispartof | Farmaco (Società chimica italiana : 1989), 2000-11, Vol.55 (11), p.665-668 |
| issn | 0014-827X 1879-0569 |
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| source | MEDLINE; Alma/SFX Local Collection |
| subjects | 1,4-Dihydropyridine Animals Aorta, Thoracic - drug effects Biological and medical sciences Calcium antagonistic activity Calcium Channel Blockers - chemical synthesis Calcium Channel Blockers - pharmacology Cardiovascular system Dihydropyridines - chemical synthesis Dihydropyridines - pharmacology Hexahydroquinoline In Vitro Techniques Magnetic Resonance Spectroscopy Male Mass Spectrometry Medical sciences Miscellaneous Muscle Contraction - drug effects Muscle, Smooth, Vascular - drug effects Pharmacology Pharmacology. Drug treatments Quinolines - chemistry Quinolines - pharmacology Rats Spectra Spectrophotometry, Infrared Spectroscopy, Fourier Transform Infrared |
| title | Synthesis and calcium antagonistic activity of 2,6,6-trimethyl-3-carbomethoxy(ethoxy)-4-aryl-1,4,5,6,7,8-hexahydroquinoline derivatives |
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