[p-[(Thienylcarbonyl)amino]phenoxy]propanolamines derivatives as diuretic and β-adrenergic receptor blocking agents
The synthesis of [[(thienylcarbonyl)amino]phenoxy]propanolamines and their beta-adrenergic blocking and diuretic activity are described. Structure-activity relationships demonstrated that ortho substitution of the phenoxy ring with an hydrogen or an ester function leads to compounds possessing both...
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| Veröffentlicht in: | Journal of medicinal chemistry 1986, Vol.29 (1), p.100-103 |
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| container_end_page | 103 |
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| container_issue | 1 |
| container_start_page | 100 |
| container_title | Journal of medicinal chemistry |
| container_volume | 29 |
| creator | BOULEY, E TEULON, J.-M CAZES, M CLOAREC, A DEGHENGHI, R |
| description | The synthesis of [[(thienylcarbonyl)amino]phenoxy]propanolamines and their beta-adrenergic blocking and diuretic activity are described. Structure-activity relationships demonstrated that ortho substitution of the phenoxy ring with an hydrogen or an ester function leads to compounds possessing both activities. Ethyl 2-[3-[(1,1-dimethylethyl) amino]-2-hydroxypropoxy]-5-[(2-thienylcarbonyl)amino]benzoate (3d) was selected as the most active compound for further investigation. |
| doi_str_mv | 10.1021/jm00151a017 |
| format | Article |
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Structure-activity relationships demonstrated that ortho substitution of the phenoxy ring with an hydrogen or an ester function leads to compounds possessing both activities. Ethyl 2-[3-[(1,1-dimethylethyl) amino]-2-hydroxypropoxy]-5-[(2-thienylcarbonyl)amino]benzoate (3d) was selected as the most active compound for further investigation.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00151a017</identifier><identifier>PMID: 3001305</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Blood Pressure - drug effects ; Chemical Phenomena ; Chemistry ; Diuresis - drug effects ; Dogs ; Exact sciences and technology ; Female ; Heart Rate - drug effects ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Male ; Myocardial Contraction - drug effects ; Organic chemistry ; Preparations and properties ; Propanolamines - chemical synthesis ; Propanolamines - pharmacology ; Rats ; Rats, Inbred Strains ; Receptors, Adrenergic, beta - drug effects ; Receptors, Adrenergic, beta - physiology ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 1986, Vol.29 (1), p.100-103</ispartof><rights>1986 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,4012,27906,27907,27908</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=8514804$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/3001305$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>BOULEY, E</creatorcontrib><creatorcontrib>TEULON, J.-M</creatorcontrib><creatorcontrib>CAZES, M</creatorcontrib><creatorcontrib>CLOAREC, A</creatorcontrib><creatorcontrib>DEGHENGHI, R</creatorcontrib><title>[p-[(Thienylcarbonyl)amino]phenoxy]propanolamines derivatives as diuretic and β-adrenergic receptor blocking agents</title><title>Journal of medicinal chemistry</title><addtitle>J Med Chem</addtitle><description>The synthesis of [[(thienylcarbonyl)amino]phenoxy]propanolamines and their beta-adrenergic blocking and diuretic activity are described. Structure-activity relationships demonstrated that ortho substitution of the phenoxy ring with an hydrogen or an ester function leads to compounds possessing both activities. Ethyl 2-[3-[(1,1-dimethylethyl) amino]-2-hydroxypropoxy]-5-[(2-thienylcarbonyl)amino]benzoate (3d) was selected as the most active compound for further investigation.</description><subject>Animals</subject><subject>Blood Pressure - drug effects</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Diuresis - drug effects</subject><subject>Dogs</subject><subject>Exact sciences and technology</subject><subject>Female</subject><subject>Heart Rate - drug effects</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Male</subject><subject>Myocardial Contraction - drug effects</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Propanolamines - chemical synthesis</subject><subject>Propanolamines - pharmacology</subject><subject>Rats</subject><subject>Rats, Inbred Strains</subject><subject>Receptors, Adrenergic, beta - drug effects</subject><subject>Receptors, Adrenergic, beta - physiology</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1986</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9UMtKxDAUDaLoOLpyLXQhootqHk0ysxTxBQNuxtUg5Ta5M0bbtCYdcX7LD_GbjFhc3Xse98I5hBwxesEoZ5evDaVMMqBMb5ERk5zmxYQW22REKec5V1zskf0YXymlgnGxS3ZFuhBUjki_6PLF2fzFod_UBkLVpnkOjfPtc_eCvv3cPHeh7cC39S-LMbMY3Af07iPtkKBbB-ydycDb7PsrBxvQY1glJqDBrm9DVtWteXN-lcEKfR8PyM4S6oiHwxyTp9ub-fV9Pnu8e7i-muUdF7LPTaH0VKRUUlEutRKorRRMAlqrCwlUMrsUxURyMdWVUtwm0RYAuuLWJDQmp39_U4L3Nca-bFw0WNfgsV3HUis1pVLpZDwejOuqQVt2wTUQNuVQU9JPBh2igXoZwBsX_20TyX4LFz_ltnhf</recordid><startdate>1986</startdate><enddate>1986</enddate><creator>BOULEY, E</creator><creator>TEULON, J.-M</creator><creator>CAZES, M</creator><creator>CLOAREC, A</creator><creator>DEGHENGHI, R</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>1986</creationdate><title>[p-[(Thienylcarbonyl)amino]phenoxy]propanolamines derivatives as diuretic and β-adrenergic receptor blocking agents</title><author>BOULEY, E ; TEULON, J.-M ; CAZES, M ; CLOAREC, A ; DEGHENGHI, R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p235t-c4679301756025763e7d5315aedd745a051df34852397b662d315d4aa7b2dc2d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1986</creationdate><topic>Animals</topic><topic>Blood Pressure - drug effects</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Diuresis - drug effects</topic><topic>Dogs</topic><topic>Exact sciences and technology</topic><topic>Female</topic><topic>Heart Rate - drug effects</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Male</topic><topic>Myocardial Contraction - drug effects</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Propanolamines - chemical synthesis</topic><topic>Propanolamines - pharmacology</topic><topic>Rats</topic><topic>Rats, Inbred Strains</topic><topic>Receptors, Adrenergic, beta - drug effects</topic><topic>Receptors, Adrenergic, beta - physiology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>BOULEY, E</creatorcontrib><creatorcontrib>TEULON, J.-M</creatorcontrib><creatorcontrib>CAZES, M</creatorcontrib><creatorcontrib>CLOAREC, A</creatorcontrib><creatorcontrib>DEGHENGHI, R</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>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>BOULEY, E</au><au>TEULON, J.-M</au><au>CAZES, M</au><au>CLOAREC, A</au><au>DEGHENGHI, R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>[p-[(Thienylcarbonyl)amino]phenoxy]propanolamines derivatives as diuretic and β-adrenergic receptor blocking agents</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J Med Chem</addtitle><date>1986</date><risdate>1986</risdate><volume>29</volume><issue>1</issue><spage>100</spage><epage>103</epage><pages>100-103</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>The synthesis of [[(thienylcarbonyl)amino]phenoxy]propanolamines and their beta-adrenergic blocking and diuretic activity are described. Structure-activity relationships demonstrated that ortho substitution of the phenoxy ring with an hydrogen or an ester function leads to compounds possessing both activities. Ethyl 2-[3-[(1,1-dimethylethyl) amino]-2-hydroxypropoxy]-5-[(2-thienylcarbonyl)amino]benzoate (3d) was selected as the most active compound for further investigation.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>3001305</pmid><doi>10.1021/jm00151a017</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1986, Vol.29 (1), p.100-103 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_76690567 |
| source | MEDLINE; ACS Publications |
| subjects | Animals Blood Pressure - drug effects Chemical Phenomena Chemistry Diuresis - drug effects Dogs Exact sciences and technology Female Heart Rate - drug effects Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Male Myocardial Contraction - drug effects Organic chemistry Preparations and properties Propanolamines - chemical synthesis Propanolamines - pharmacology Rats Rats, Inbred Strains Receptors, Adrenergic, beta - drug effects Receptors, Adrenergic, beta - physiology Structure-Activity Relationship |
| title | [p-[(Thienylcarbonyl)amino]phenoxy]propanolamines derivatives as diuretic and β-adrenergic receptor blocking agents |
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