Synthesis and antifibrillatory activity of nibentan and its analogues
A series of 1,5-diaminopentane derivatives, structurally related to nibentan, was synthesized and tested for antifibrillatory activity. Improved modifications of some known chemical syntheses were proposed. (±)-N-[5-(Diethylamino)-1-(4-nitrophenyl)pentyl]-benzamide hydrochloride, (±)-N-[5-(diethylam...
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| Veröffentlicht in: | European journal of medicinal chemistry 2000-02, Vol.35 (2), p.205-215 |
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| container_title | European journal of medicinal chemistry |
| container_volume | 35 |
| creator | Davydova, Nadejda K Sizova, Olga S Vinogradova, Svetlana M L'vov, Alexandre I Glushkov, Robert G Yuzhakov, Sergey D Mashkovskiy, Michail D |
| description | A series of 1,5-diaminopentane derivatives, structurally related to nibentan, was synthesized and tested for antifibrillatory activity. Improved modifications of some known chemical syntheses were proposed. (±)-N-[5-(Diethylamino)-1-(4-nitrophenyl)pentyl]-benzamide hydrochloride, (±)-N-[5-(diethylamino)-1-(4-nitrophenyl)pentyl]-4-nitrobenzamide hydrochloride and (±)-N-[5-(diethylamino)-1-(4-hydroxyphenyl)pentyl]-4-nitrobenzamide hydrochloride were more potent than nibentan and possessed a longer duration of action (up to 5 h in comparison with 60–90 min for nibentan). The antifibrillatory activity of (±)-N-[5-(diethylamino)-1-(4-methoxyphenyl)pentyl]-4-nitrobenzamide hydrochloride was comparable to that of nibentan but exceeded the potency of D-sotalol and sematilide. |
| doi_str_mv | 10.1016/S0223-5234(00)00116-1 |
| format | Article |
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Improved modifications of some known chemical syntheses were proposed. (±)-N-[5-(Diethylamino)-1-(4-nitrophenyl)pentyl]-benzamide hydrochloride, (±)-N-[5-(diethylamino)-1-(4-nitrophenyl)pentyl]-4-nitrobenzamide hydrochloride and (±)-N-[5-(diethylamino)-1-(4-hydroxyphenyl)pentyl]-4-nitrobenzamide hydrochloride were more potent than nibentan and possessed a longer duration of action (up to 5 h in comparison with 60–90 min for nibentan). The antifibrillatory activity of (±)-N-[5-(diethylamino)-1-(4-methoxyphenyl)pentyl]-4-nitrobenzamide hydrochloride was comparable to that of nibentan but exceeded the potency of D-sotalol and sematilide.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/S0223-5234(00)00116-1</identifier><identifier>PMID: 10758282</identifier><language>eng</language><publisher>France: Elsevier Masson SAS</publisher><subject>1,5-diaminopentane derivatives ; Animals ; Anti-Arrhythmia Agents - chemical synthesis ; Anti-Arrhythmia Agents - pharmacology ; antifibrillatory activity ; Benzamides - chemical synthesis ; Benzamides - pharmacology ; Cats ; Diamines - chemical synthesis ; Diamines - pharmacology ; Electric Stimulation ; Heart Ventricles - drug effects ; Heart Ventricles - physiopathology ; nibentan ; Pentanes - chemical synthesis ; Pentanes - pharmacology ; Structure-Activity Relationship ; structure–activity relationships ; synthesis ; Ventricular Fibrillation - physiopathology ; Ventricular Fibrillation - prevention & control ; Ventricular Function</subject><ispartof>European journal of medicinal chemistry, 2000-02, Vol.35 (2), p.205-215</ispartof><rights>2000 Éditions scientifiques et médicales Elsevier SAS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c361t-1dd0d297a30b682ce460730307ab5b851edda0a738ea5b632f657d084ecd89493</citedby><cites>FETCH-LOGICAL-c361t-1dd0d297a30b682ce460730307ab5b851edda0a738ea5b632f657d084ecd89493</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0223523400001161$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10758282$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Davydova, Nadejda K</creatorcontrib><creatorcontrib>Sizova, Olga S</creatorcontrib><creatorcontrib>Vinogradova, Svetlana M</creatorcontrib><creatorcontrib>L'vov, Alexandre I</creatorcontrib><creatorcontrib>Glushkov, Robert G</creatorcontrib><creatorcontrib>Yuzhakov, Sergey D</creatorcontrib><creatorcontrib>Mashkovskiy, Michail D</creatorcontrib><title>Synthesis and antifibrillatory activity of nibentan and its analogues</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>A series of 1,5-diaminopentane derivatives, structurally related to nibentan, was synthesized and tested for antifibrillatory activity. Improved modifications of some known chemical syntheses were proposed. (±)-N-[5-(Diethylamino)-1-(4-nitrophenyl)pentyl]-benzamide hydrochloride, (±)-N-[5-(diethylamino)-1-(4-nitrophenyl)pentyl]-4-nitrobenzamide hydrochloride and (±)-N-[5-(diethylamino)-1-(4-hydroxyphenyl)pentyl]-4-nitrobenzamide hydrochloride were more potent than nibentan and possessed a longer duration of action (up to 5 h in comparison with 60–90 min for nibentan). The antifibrillatory activity of (±)-N-[5-(diethylamino)-1-(4-methoxyphenyl)pentyl]-4-nitrobenzamide hydrochloride was comparable to that of nibentan but exceeded the potency of D-sotalol and sematilide.</description><subject>1,5-diaminopentane derivatives</subject><subject>Animals</subject><subject>Anti-Arrhythmia Agents - chemical synthesis</subject><subject>Anti-Arrhythmia Agents - pharmacology</subject><subject>antifibrillatory activity</subject><subject>Benzamides - chemical synthesis</subject><subject>Benzamides - pharmacology</subject><subject>Cats</subject><subject>Diamines - chemical synthesis</subject><subject>Diamines - pharmacology</subject><subject>Electric Stimulation</subject><subject>Heart Ventricles - drug effects</subject><subject>Heart Ventricles - physiopathology</subject><subject>nibentan</subject><subject>Pentanes - chemical synthesis</subject><subject>Pentanes - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>structure–activity relationships</subject><subject>synthesis</subject><subject>Ventricular Fibrillation - physiopathology</subject><subject>Ventricular Fibrillation - prevention & control</subject><subject>Ventricular Function</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkE1LAzEQhoMotlZ_gtKT6GF1kmyS7Umk1A8oeKieQzaZ1ch2V5O0sP_e7QfizcOQy_PmnXkIOadwQ4HK2wUwxjPBeH4FcA1AqczoARlSJYuMM5EfkuEvMiAnMX4CgJAAx2RAQYmCFWxIZouuSR8YfRybxvWTfOXL4OvapDZ0Y2OTX_vUjdtq3PgSm2SaLenTJmHq9n2F8ZQcVaaOeLZ_R-TtYfY6fcrmL4_P0_t5ZrmkKaPOgWMTZTiUsmAWcwmKAwdlSlEWgqJzBoziBRpRSs4qKZSDIkfrikk-4SNyufv3K7TffW_SSx8t9ss22K6iVhS4oEr1oNiBNrQxBqz0V_BLEzpNQW_86a0_vZGjAfTWn6Z97mJfsCqX6P6kdsJ64G4HYH_m2mPQ0XpsLDof0CbtWv9PxQ9Cqn9K</recordid><startdate>20000201</startdate><enddate>20000201</enddate><creator>Davydova, Nadejda K</creator><creator>Sizova, Olga S</creator><creator>Vinogradova, Svetlana M</creator><creator>L'vov, Alexandre I</creator><creator>Glushkov, Robert G</creator><creator>Yuzhakov, Sergey D</creator><creator>Mashkovskiy, Michail D</creator><general>Elsevier Masson SAS</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>7X8</scope></search><sort><creationdate>20000201</creationdate><title>Synthesis and antifibrillatory activity of nibentan and its analogues</title><author>Davydova, Nadejda K ; Sizova, Olga S ; Vinogradova, Svetlana M ; L'vov, Alexandre I ; Glushkov, Robert G ; Yuzhakov, Sergey D ; Mashkovskiy, Michail D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c361t-1dd0d297a30b682ce460730307ab5b851edda0a738ea5b632f657d084ecd89493</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>1,5-diaminopentane derivatives</topic><topic>Animals</topic><topic>Anti-Arrhythmia Agents - chemical synthesis</topic><topic>Anti-Arrhythmia Agents - pharmacology</topic><topic>antifibrillatory activity</topic><topic>Benzamides - chemical synthesis</topic><topic>Benzamides - pharmacology</topic><topic>Cats</topic><topic>Diamines - chemical synthesis</topic><topic>Diamines - pharmacology</topic><topic>Electric Stimulation</topic><topic>Heart Ventricles - drug effects</topic><topic>Heart Ventricles - physiopathology</topic><topic>nibentan</topic><topic>Pentanes - chemical synthesis</topic><topic>Pentanes - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>structure–activity relationships</topic><topic>synthesis</topic><topic>Ventricular Fibrillation - physiopathology</topic><topic>Ventricular Fibrillation - prevention & control</topic><topic>Ventricular Function</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Davydova, Nadejda K</creatorcontrib><creatorcontrib>Sizova, Olga S</creatorcontrib><creatorcontrib>Vinogradova, Svetlana M</creatorcontrib><creatorcontrib>L'vov, Alexandre I</creatorcontrib><creatorcontrib>Glushkov, Robert G</creatorcontrib><creatorcontrib>Yuzhakov, Sergey D</creatorcontrib><creatorcontrib>Mashkovskiy, Michail D</creatorcontrib><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>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Davydova, Nadejda K</au><au>Sizova, Olga S</au><au>Vinogradova, Svetlana M</au><au>L'vov, Alexandre I</au><au>Glushkov, Robert G</au><au>Yuzhakov, Sergey D</au><au>Mashkovskiy, Michail D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and antifibrillatory activity of nibentan and its analogues</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2000-02-01</date><risdate>2000</risdate><volume>35</volume><issue>2</issue><spage>205</spage><epage>215</epage><pages>205-215</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><abstract>A series of 1,5-diaminopentane derivatives, structurally related to nibentan, was synthesized and tested for antifibrillatory activity. Improved modifications of some known chemical syntheses were proposed. (±)-N-[5-(Diethylamino)-1-(4-nitrophenyl)pentyl]-benzamide hydrochloride, (±)-N-[5-(diethylamino)-1-(4-nitrophenyl)pentyl]-4-nitrobenzamide hydrochloride and (±)-N-[5-(diethylamino)-1-(4-hydroxyphenyl)pentyl]-4-nitrobenzamide hydrochloride were more potent than nibentan and possessed a longer duration of action (up to 5 h in comparison with 60–90 min for nibentan). The antifibrillatory activity of (±)-N-[5-(diethylamino)-1-(4-methoxyphenyl)pentyl]-4-nitrobenzamide hydrochloride was comparable to that of nibentan but exceeded the potency of D-sotalol and sematilide.</abstract><cop>France</cop><pub>Elsevier Masson SAS</pub><pmid>10758282</pmid><doi>10.1016/S0223-5234(00)00116-1</doi><tpages>11</tpages></addata></record> |
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| subjects | 1,5-diaminopentane derivatives Animals Anti-Arrhythmia Agents - chemical synthesis Anti-Arrhythmia Agents - pharmacology antifibrillatory activity Benzamides - chemical synthesis Benzamides - pharmacology Cats Diamines - chemical synthesis Diamines - pharmacology Electric Stimulation Heart Ventricles - drug effects Heart Ventricles - physiopathology nibentan Pentanes - chemical synthesis Pentanes - pharmacology Structure-Activity Relationship structure–activity relationships synthesis Ventricular Fibrillation - physiopathology Ventricular Fibrillation - prevention & control Ventricular Function |
| title | Synthesis and antifibrillatory activity of nibentan and its analogues |
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