Synthesis and Pharmacological Activity of a New Series of 1-(1H-Indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol Analogs
β‐Adrenergic receptor antagonists are important therapeutics for the treatment of cardiovascular disorders. In the group of β‐blockers, much attention is being paid to the third‐generation drugs that possess important ancillary properties besides inhibiting β‐adrenoceptors. Vasodilating activity of...
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| Veröffentlicht in: | Archiv der Pharmazie (Weinheim) 2016-03, Vol.349 (3), p.211-223 |
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| creator | Bednarski, Marek Otto, Monika Dudek, Magdalena Kołaczkowski, Marcin Bucki, Adam Siwek, Agata Groszek, Grażyna Maziarz, Elżbieta Wilk, Piotr Sapa, Jacek |
| description | β‐Adrenergic receptor antagonists are important therapeutics for the treatment of cardiovascular disorders. In the group of β‐blockers, much attention is being paid to the third‐generation drugs that possess important ancillary properties besides inhibiting β‐adrenoceptors. Vasodilating activity of these drugs is produced through different mechanisms, such as nitric oxide (NO) release, β2‐agonistic action, α1‐blockade, antioxidant action, and Ca2+ entry blockade. Here, a study on evaluation of the cardiovascular activity of five new compounds is presented. Compound 3a is a methyl and four of the tested compounds (3b–e) are dimethoxy derivatives of 1‐(1H‐indol‐4‐yloxy)‐3‐(2‐(2‐methoxyphenoxy)ethylamino)propan‐2‐ol. The obtained results confirmed that the methyl and dimethoxy derivatives of 1‐(1H‐indol‐4‐yloxy)‐3‐(2‐(2‐methoxyphenoxy)ethylamino)propan‐2‐ol and their enantiomers possess α1‐ and β1‐adrenolytic activities and that the antiarrhythmic and hypotensive effects of the tested compounds are related to their adrenolytic properties.
Five new derivatives of 1‐(1H‐indol‐4‐yloxy)‐3‐(2‐(2‐methoxyphenoxy)‐ethylamino)propan‐2‐ol (methyl and dimethoxy derivatives) are evaluated for their cardiovascular activities. All derivatives and their enantiomers possess α1‐ and β1‐adrenolytic activities. The antiarrhythmic and hypotensive effects of the tested compounds are related to their adrenolytic properties. |
| doi_str_mv | 10.1002/ardp.201500234 |
| format | Article |
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Five new derivatives of 1‐(1H‐indol‐4‐yloxy)‐3‐(2‐(2‐methoxyphenoxy)‐ethylamino)propan‐2‐ol (methyl and dimethoxy derivatives) are evaluated for their cardiovascular activities. All derivatives and their enantiomers possess α1‐ and β1‐adrenolytic activities. The antiarrhythmic and hypotensive effects of the tested compounds are related to their adrenolytic properties.</description><identifier>ISSN: 0365-6233</identifier><identifier>EISSN: 1521-4184</identifier><identifier>DOI: 10.1002/ardp.201500234</identifier><identifier>PMID: 26853441</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Animals ; Anti-Arrhythmia Agents - chemical synthesis ; Anti-Arrhythmia Agents - chemistry ; Anti-Arrhythmia Agents - pharmacology ; Antihypertensive Agents - chemical synthesis ; Antihypertensive Agents - chemistry ; Antihypertensive Agents - pharmacology ; Blood Pressure - drug effects ; Cardiovascular activity ; Enantiomers ; Ethylamines - chemical synthesis ; Ethylamines - chemistry ; Ethylamines - pharmacology ; Indoles - chemical synthesis ; Indoles - chemistry ; Indoles - pharmacology ; Models, Molecular ; Propanols - chemical synthesis ; Propanols - chemistry ; Propanols - pharmacology ; Radioligand Assay ; Rats ; Receptors, Adrenergic, alpha-1 - chemistry ; Receptors, Adrenergic, alpha-1 - metabolism ; Receptors, Adrenergic, beta-1 - chemistry ; Receptors, Adrenergic, beta-1 - metabolism ; Stereoisomerism ; Structure-Activity Relationship ; Synthesis ; Vasodilator Agents - chemical synthesis ; Vasodilator Agents - chemistry ; Vasodilator Agents - pharmacology ; α1‐, α2‐, β1‐Adrenoreceptor antagonists ; β1-Adrenoreceptor antagonists</subject><ispartof>Archiv der Pharmazie (Weinheim), 2016-03, Vol.349 (3), p.211-223</ispartof><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4114-b0328a8de18d998806e7c59822d094056df7e3f8ac86794a37d0652b6e3a778d3</citedby><cites>FETCH-LOGICAL-c4114-b0328a8de18d998806e7c59822d094056df7e3f8ac86794a37d0652b6e3a778d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fardp.201500234$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fardp.201500234$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45579,45580</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26853441$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bednarski, Marek</creatorcontrib><creatorcontrib>Otto, Monika</creatorcontrib><creatorcontrib>Dudek, Magdalena</creatorcontrib><creatorcontrib>Kołaczkowski, Marcin</creatorcontrib><creatorcontrib>Bucki, Adam</creatorcontrib><creatorcontrib>Siwek, Agata</creatorcontrib><creatorcontrib>Groszek, Grażyna</creatorcontrib><creatorcontrib>Maziarz, Elżbieta</creatorcontrib><creatorcontrib>Wilk, Piotr</creatorcontrib><creatorcontrib>Sapa, Jacek</creatorcontrib><title>Synthesis and Pharmacological Activity of a New Series of 1-(1H-Indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol Analogs</title><title>Archiv der Pharmazie (Weinheim)</title><addtitle>Arch. Pharm. Chem. Life Sci</addtitle><description>β‐Adrenergic receptor antagonists are important therapeutics for the treatment of cardiovascular disorders. In the group of β‐blockers, much attention is being paid to the third‐generation drugs that possess important ancillary properties besides inhibiting β‐adrenoceptors. Vasodilating activity of these drugs is produced through different mechanisms, such as nitric oxide (NO) release, β2‐agonistic action, α1‐blockade, antioxidant action, and Ca2+ entry blockade. Here, a study on evaluation of the cardiovascular activity of five new compounds is presented. Compound 3a is a methyl and four of the tested compounds (3b–e) are dimethoxy derivatives of 1‐(1H‐indol‐4‐yloxy)‐3‐(2‐(2‐methoxyphenoxy)ethylamino)propan‐2‐ol. The obtained results confirmed that the methyl and dimethoxy derivatives of 1‐(1H‐indol‐4‐yloxy)‐3‐(2‐(2‐methoxyphenoxy)ethylamino)propan‐2‐ol and their enantiomers possess α1‐ and β1‐adrenolytic activities and that the antiarrhythmic and hypotensive effects of the tested compounds are related to their adrenolytic properties.
Five new derivatives of 1‐(1H‐indol‐4‐yloxy)‐3‐(2‐(2‐methoxyphenoxy)‐ethylamino)propan‐2‐ol (methyl and dimethoxy derivatives) are evaluated for their cardiovascular activities. All derivatives and their enantiomers possess α1‐ and β1‐adrenolytic activities. The antiarrhythmic and hypotensive effects of the tested compounds are related to their adrenolytic properties.</description><subject>Animals</subject><subject>Anti-Arrhythmia Agents - chemical synthesis</subject><subject>Anti-Arrhythmia Agents - chemistry</subject><subject>Anti-Arrhythmia Agents - pharmacology</subject><subject>Antihypertensive Agents - chemical synthesis</subject><subject>Antihypertensive Agents - chemistry</subject><subject>Antihypertensive Agents - pharmacology</subject><subject>Blood Pressure - drug effects</subject><subject>Cardiovascular activity</subject><subject>Enantiomers</subject><subject>Ethylamines - chemical synthesis</subject><subject>Ethylamines - chemistry</subject><subject>Ethylamines - pharmacology</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>Indoles - pharmacology</subject><subject>Models, Molecular</subject><subject>Propanols - chemical synthesis</subject><subject>Propanols - chemistry</subject><subject>Propanols - pharmacology</subject><subject>Radioligand Assay</subject><subject>Rats</subject><subject>Receptors, Adrenergic, alpha-1 - chemistry</subject><subject>Receptors, Adrenergic, alpha-1 - metabolism</subject><subject>Receptors, Adrenergic, beta-1 - chemistry</subject><subject>Receptors, Adrenergic, beta-1 - metabolism</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><subject>Synthesis</subject><subject>Vasodilator Agents - chemical synthesis</subject><subject>Vasodilator Agents - chemistry</subject><subject>Vasodilator Agents - pharmacology</subject><subject>α1‐, α2‐, β1‐Adrenoreceptor antagonists</subject><subject>β1-Adrenoreceptor antagonists</subject><issn>0365-6233</issn><issn>1521-4184</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc9rFDEcxYNY7Fq9epQBL9tDtvk1Sea4tNqWlm21SsFLyE4yburMZExmbefuH94M0y7iRQiE9-Xz3vcLD4B3GC0wQuRIB9MtCMJ5EpS9ADOcEwwZluwlmCHKc8gJpfvgdYx3CCGKSP4K7BMuc8oYnoE_N0Pbb2x0MdOtya43OjS69LX_4UpdZ8uyd79dP2S-ynS2svfZjQ3OxlFjOMdn8Lw1voYMDrV_GA4hhXMyvsb2mzToNrYd50kNtW5c6w-74DvdQgJ9im912hTfgL1K19G-ffoPwLdPH78en8HLq9Pz4-UlLBnGDK4RJVJLY7E0RSEl4laUeSEJMahgKOemEpZWUpeSi4JpKgziOVlzS7UQ0tADMJ9y0w2_tjb2qnGxtHWtW-u3UWEhkBS4QCKhH_5B7_w2pHMnChHMOE_UYqLK4GMMtlJdcI0Og8JIjf2osR-16ycZ3j_FbteNNTv8uZAEFBNw72o7_CdOLb-cXP8dDievi7192Hl1-Km4oCJXt6tTtfq8umXy-4XC9BFg-qkS</recordid><startdate>201603</startdate><enddate>201603</enddate><creator>Bednarski, Marek</creator><creator>Otto, Monika</creator><creator>Dudek, Magdalena</creator><creator>Kołaczkowski, Marcin</creator><creator>Bucki, Adam</creator><creator>Siwek, Agata</creator><creator>Groszek, Grażyna</creator><creator>Maziarz, Elżbieta</creator><creator>Wilk, Piotr</creator><creator>Sapa, Jacek</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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>K9.</scope><scope>7X8</scope></search><sort><creationdate>201603</creationdate><title>Synthesis and Pharmacological Activity of a New Series of 1-(1H-Indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol Analogs</title><author>Bednarski, Marek ; Otto, Monika ; Dudek, Magdalena ; Kołaczkowski, Marcin ; Bucki, Adam ; Siwek, Agata ; Groszek, Grażyna ; Maziarz, Elżbieta ; Wilk, Piotr ; Sapa, Jacek</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4114-b0328a8de18d998806e7c59822d094056df7e3f8ac86794a37d0652b6e3a778d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Animals</topic><topic>Anti-Arrhythmia Agents - chemical synthesis</topic><topic>Anti-Arrhythmia Agents - chemistry</topic><topic>Anti-Arrhythmia Agents - pharmacology</topic><topic>Antihypertensive Agents - chemical synthesis</topic><topic>Antihypertensive Agents - chemistry</topic><topic>Antihypertensive Agents - pharmacology</topic><topic>Blood Pressure - drug effects</topic><topic>Cardiovascular activity</topic><topic>Enantiomers</topic><topic>Ethylamines - chemical synthesis</topic><topic>Ethylamines - chemistry</topic><topic>Ethylamines - pharmacology</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Indoles - pharmacology</topic><topic>Models, Molecular</topic><topic>Propanols - chemical synthesis</topic><topic>Propanols - chemistry</topic><topic>Propanols - pharmacology</topic><topic>Radioligand Assay</topic><topic>Rats</topic><topic>Receptors, Adrenergic, alpha-1 - chemistry</topic><topic>Receptors, Adrenergic, alpha-1 - metabolism</topic><topic>Receptors, Adrenergic, beta-1 - chemistry</topic><topic>Receptors, Adrenergic, beta-1 - metabolism</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><topic>Synthesis</topic><topic>Vasodilator Agents - chemical synthesis</topic><topic>Vasodilator Agents - chemistry</topic><topic>Vasodilator Agents - pharmacology</topic><topic>α1‐, α2‐, β1‐Adrenoreceptor antagonists</topic><topic>β1-Adrenoreceptor antagonists</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bednarski, Marek</creatorcontrib><creatorcontrib>Otto, Monika</creatorcontrib><creatorcontrib>Dudek, Magdalena</creatorcontrib><creatorcontrib>Kołaczkowski, Marcin</creatorcontrib><creatorcontrib>Bucki, Adam</creatorcontrib><creatorcontrib>Siwek, Agata</creatorcontrib><creatorcontrib>Groszek, Grażyna</creatorcontrib><creatorcontrib>Maziarz, Elżbieta</creatorcontrib><creatorcontrib>Wilk, Piotr</creatorcontrib><creatorcontrib>Sapa, Jacek</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Archiv der Pharmazie (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bednarski, Marek</au><au>Otto, Monika</au><au>Dudek, Magdalena</au><au>Kołaczkowski, Marcin</au><au>Bucki, Adam</au><au>Siwek, Agata</au><au>Groszek, Grażyna</au><au>Maziarz, Elżbieta</au><au>Wilk, Piotr</au><au>Sapa, Jacek</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Pharmacological Activity of a New Series of 1-(1H-Indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol Analogs</atitle><jtitle>Archiv der Pharmazie (Weinheim)</jtitle><addtitle>Arch. Pharm. Chem. Life Sci</addtitle><date>2016-03</date><risdate>2016</risdate><volume>349</volume><issue>3</issue><spage>211</spage><epage>223</epage><pages>211-223</pages><issn>0365-6233</issn><eissn>1521-4184</eissn><abstract>β‐Adrenergic receptor antagonists are important therapeutics for the treatment of cardiovascular disorders. In the group of β‐blockers, much attention is being paid to the third‐generation drugs that possess important ancillary properties besides inhibiting β‐adrenoceptors. Vasodilating activity of these drugs is produced through different mechanisms, such as nitric oxide (NO) release, β2‐agonistic action, α1‐blockade, antioxidant action, and Ca2+ entry blockade. Here, a study on evaluation of the cardiovascular activity of five new compounds is presented. Compound 3a is a methyl and four of the tested compounds (3b–e) are dimethoxy derivatives of 1‐(1H‐indol‐4‐yloxy)‐3‐(2‐(2‐methoxyphenoxy)ethylamino)propan‐2‐ol. The obtained results confirmed that the methyl and dimethoxy derivatives of 1‐(1H‐indol‐4‐yloxy)‐3‐(2‐(2‐methoxyphenoxy)ethylamino)propan‐2‐ol and their enantiomers possess α1‐ and β1‐adrenolytic activities and that the antiarrhythmic and hypotensive effects of the tested compounds are related to their adrenolytic properties.
Five new derivatives of 1‐(1H‐indol‐4‐yloxy)‐3‐(2‐(2‐methoxyphenoxy)‐ethylamino)propan‐2‐ol (methyl and dimethoxy derivatives) are evaluated for their cardiovascular activities. All derivatives and their enantiomers possess α1‐ and β1‐adrenolytic activities. The antiarrhythmic and hypotensive effects of the tested compounds are related to their adrenolytic properties.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>26853441</pmid><doi>10.1002/ardp.201500234</doi><tpages>13</tpages></addata></record> |
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| ispartof | Archiv der Pharmazie (Weinheim), 2016-03, Vol.349 (3), p.211-223 |
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| subjects | Animals Anti-Arrhythmia Agents - chemical synthesis Anti-Arrhythmia Agents - chemistry Anti-Arrhythmia Agents - pharmacology Antihypertensive Agents - chemical synthesis Antihypertensive Agents - chemistry Antihypertensive Agents - pharmacology Blood Pressure - drug effects Cardiovascular activity Enantiomers Ethylamines - chemical synthesis Ethylamines - chemistry Ethylamines - pharmacology Indoles - chemical synthesis Indoles - chemistry Indoles - pharmacology Models, Molecular Propanols - chemical synthesis Propanols - chemistry Propanols - pharmacology Radioligand Assay Rats Receptors, Adrenergic, alpha-1 - chemistry Receptors, Adrenergic, alpha-1 - metabolism Receptors, Adrenergic, beta-1 - chemistry Receptors, Adrenergic, beta-1 - metabolism Stereoisomerism Structure-Activity Relationship Synthesis Vasodilator Agents - chemical synthesis Vasodilator Agents - chemistry Vasodilator Agents - pharmacology α1‐, α2‐, β1‐Adrenoreceptor antagonists β1-Adrenoreceptor antagonists |
| title | Synthesis and Pharmacological Activity of a New Series of 1-(1H-Indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol Analogs |
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