Discovery of novel N-acylsulfonamide analogs as potent and selective EP3 receptor antagonists
Identification of novel N-acyl 3,4-difluorobenzenesulfonamide analogs as potent and selective EP3 receptor antagonists and their in vivo efficacy with respect to the PGE 2-induced uterine contraction in pregnant rats are reported. A series of novel N-acylsulfonamide analogs were synthesized and eval...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2010-04, Vol.20 (8), p.2639-2643 |
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| creator | Asada, Masaki Obitsu, Tetsuo Kinoshita, Atsushi Nakai, Yoshihiko Nagase, Toshihiko Sugimoto, Isamu Tanaka, Motoyuki Takizawa, Hiroya Yoshikawa, Ken Sato, Kazutoyo Narita, Masami Ohuchida, Shuichi Nakai, Hisao Toda, Masaaki |
| description | Identification of novel
N-acyl 3,4-difluorobenzenesulfonamide analogs as potent and selective EP3 receptor antagonists and their in vivo efficacy with respect to the PGE
2-induced uterine contraction in pregnant rats are reported.
A series of novel
N-acylsulfonamide analogs were synthesized and evaluated for their binding affinity and antagonist activity for the EP3 receptor subtype. Representative compounds were also evaluated for their inhibitory effect on PGE
2-induced uterine contraction in pregnant rats. Among those tested, a series of
N-acylbenzenesulfonamide analogs were found to be more potent than the corresponding carboxylic acid analogs in both the in vitro and in vivo evaluations. The structure activity relationships (SAR) are also discussed. |
| doi_str_mv | 10.1016/j.bmcl.2010.02.034 |
| format | Article |
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N-acyl 3,4-difluorobenzenesulfonamide analogs as potent and selective EP3 receptor antagonists and their in vivo efficacy with respect to the PGE
2-induced uterine contraction in pregnant rats are reported.
A series of novel
N-acylsulfonamide analogs were synthesized and evaluated for their binding affinity and antagonist activity for the EP3 receptor subtype. Representative compounds were also evaluated for their inhibitory effect on PGE
2-induced uterine contraction in pregnant rats. Among those tested, a series of
N-acylbenzenesulfonamide analogs were found to be more potent than the corresponding carboxylic acid analogs in both the in vitro and in vivo evaluations. The structure activity relationships (SAR) are also discussed.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2010.02.034</identifier><identifier>PMID: 20346663</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Animals ; Antagonist ; Biological and medical sciences ; Dinoprostone - pharmacology ; Drug Discovery ; EP3 receptor ; Female ; Medical sciences ; Miscellaneous ; N-Acyl (3,4-difluorobenzene)sulfonamide ; N-Acylsulfonamide ; Pharmacology. Drug treatments ; Pregnancy ; Prostaglandin ; Rats ; Receptors, Prostaglandin E - antagonists & inhibitors ; Receptors, Prostaglandin E, EP3 Subtype ; Structure-Activity Relationship ; Sulfonamides - chemistry ; Sulfonamides - pharmacology ; Uterine Contraction - drug effects</subject><ispartof>Bioorganic & medicinal chemistry letters, 2010-04, Vol.20 (8), p.2639-2643</ispartof><rights>2010</rights><rights>2015 INIST-CNRS</rights><rights>Copyright 2010. Published by Elsevier Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c417t-644ce24f2272b80c540b39143477b4446662b52b6fcaec25b002e7a827abfaa13</citedby><cites>FETCH-LOGICAL-c417t-644ce24f2272b80c540b39143477b4446662b52b6fcaec25b002e7a827abfaa13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2010.02.034$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22824977$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20346663$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Asada, Masaki</creatorcontrib><creatorcontrib>Obitsu, Tetsuo</creatorcontrib><creatorcontrib>Kinoshita, Atsushi</creatorcontrib><creatorcontrib>Nakai, Yoshihiko</creatorcontrib><creatorcontrib>Nagase, Toshihiko</creatorcontrib><creatorcontrib>Sugimoto, Isamu</creatorcontrib><creatorcontrib>Tanaka, Motoyuki</creatorcontrib><creatorcontrib>Takizawa, Hiroya</creatorcontrib><creatorcontrib>Yoshikawa, Ken</creatorcontrib><creatorcontrib>Sato, Kazutoyo</creatorcontrib><creatorcontrib>Narita, Masami</creatorcontrib><creatorcontrib>Ohuchida, Shuichi</creatorcontrib><creatorcontrib>Nakai, Hisao</creatorcontrib><creatorcontrib>Toda, Masaaki</creatorcontrib><title>Discovery of novel N-acylsulfonamide analogs as potent and selective EP3 receptor antagonists</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Identification of novel
N-acyl 3,4-difluorobenzenesulfonamide analogs as potent and selective EP3 receptor antagonists and their in vivo efficacy with respect to the PGE
2-induced uterine contraction in pregnant rats are reported.
A series of novel
N-acylsulfonamide analogs were synthesized and evaluated for their binding affinity and antagonist activity for the EP3 receptor subtype. Representative compounds were also evaluated for their inhibitory effect on PGE
2-induced uterine contraction in pregnant rats. Among those tested, a series of
N-acylbenzenesulfonamide analogs were found to be more potent than the corresponding carboxylic acid analogs in both the in vitro and in vivo evaluations. The structure activity relationships (SAR) are also discussed.</description><subject>Animals</subject><subject>Antagonist</subject><subject>Biological and medical sciences</subject><subject>Dinoprostone - pharmacology</subject><subject>Drug Discovery</subject><subject>EP3 receptor</subject><subject>Female</subject><subject>Medical sciences</subject><subject>Miscellaneous</subject><subject>N-Acyl (3,4-difluorobenzene)sulfonamide</subject><subject>N-Acylsulfonamide</subject><subject>Pharmacology. Drug treatments</subject><subject>Pregnancy</subject><subject>Prostaglandin</subject><subject>Rats</subject><subject>Receptors, Prostaglandin E - antagonists & inhibitors</subject><subject>Receptors, Prostaglandin E, EP3 Subtype</subject><subject>Structure-Activity Relationship</subject><subject>Sulfonamides - chemistry</subject><subject>Sulfonamides - pharmacology</subject><subject>Uterine Contraction - drug effects</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM2KFDEURoMoTjv6Ai4kG3FVbX5uparBjcyMozCoCwU3EpLUrSFNqtIm6YZ-e1N0O-50lXBz7seXQ8hLztaccfV2u7aTC2vB6oCJNZPwiKw4KGgksPYxWbGNYk2_gR8X5FnOW8Y4MICn5EJUViklV-Tntc8uHjAdaRzpXG-Bfm6MO4a8D2OczeQHpGY2Id5najLdxYJzqZOBZgzoij8gvfkqaUKHuxJTfSrmPs4-l_ycPBlNyPjifF6S7x9uvl19bO6-3H66en_XOOBdaRSAQwGjEJ2wPXMtMCs3HCR0nQVYqgrbCqtGZ9CJ1jImsDO96IwdjeHykrw55e5S_LXHXPRUv4UhmBnjPusOFG-VYt3_SSn7Vii5ZIoT6VLMOeGod8lPJh01Z3rxr7d68a8X_5oJXZ3WpVfn-L2dcHhY-SO8Aq_PgMnOhDGZ2fn8lxO9gE239Hx34rBqO3hMOjuPs8PBV9FFD9H_q8dvFhOjJA</recordid><startdate>20100415</startdate><enddate>20100415</enddate><creator>Asada, Masaki</creator><creator>Obitsu, Tetsuo</creator><creator>Kinoshita, Atsushi</creator><creator>Nakai, Yoshihiko</creator><creator>Nagase, Toshihiko</creator><creator>Sugimoto, Isamu</creator><creator>Tanaka, Motoyuki</creator><creator>Takizawa, Hiroya</creator><creator>Yoshikawa, Ken</creator><creator>Sato, Kazutoyo</creator><creator>Narita, Masami</creator><creator>Ohuchida, Shuichi</creator><creator>Nakai, Hisao</creator><creator>Toda, Masaaki</creator><general>Elsevier Ltd</general><general>Elsevier</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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20100415</creationdate><title>Discovery of novel N-acylsulfonamide analogs as potent and selective EP3 receptor antagonists</title><author>Asada, Masaki ; Obitsu, Tetsuo ; Kinoshita, Atsushi ; Nakai, Yoshihiko ; Nagase, Toshihiko ; Sugimoto, Isamu ; Tanaka, Motoyuki ; Takizawa, Hiroya ; Yoshikawa, Ken ; Sato, Kazutoyo ; Narita, Masami ; Ohuchida, Shuichi ; Nakai, Hisao ; Toda, Masaaki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c417t-644ce24f2272b80c540b39143477b4446662b52b6fcaec25b002e7a827abfaa13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Animals</topic><topic>Antagonist</topic><topic>Biological and medical sciences</topic><topic>Dinoprostone - pharmacology</topic><topic>Drug Discovery</topic><topic>EP3 receptor</topic><topic>Female</topic><topic>Medical sciences</topic><topic>Miscellaneous</topic><topic>N-Acyl (3,4-difluorobenzene)sulfonamide</topic><topic>N-Acylsulfonamide</topic><topic>Pharmacology. Drug treatments</topic><topic>Pregnancy</topic><topic>Prostaglandin</topic><topic>Rats</topic><topic>Receptors, Prostaglandin E - antagonists & inhibitors</topic><topic>Receptors, Prostaglandin E, EP3 Subtype</topic><topic>Structure-Activity Relationship</topic><topic>Sulfonamides - chemistry</topic><topic>Sulfonamides - pharmacology</topic><topic>Uterine Contraction - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Asada, Masaki</creatorcontrib><creatorcontrib>Obitsu, Tetsuo</creatorcontrib><creatorcontrib>Kinoshita, Atsushi</creatorcontrib><creatorcontrib>Nakai, Yoshihiko</creatorcontrib><creatorcontrib>Nagase, Toshihiko</creatorcontrib><creatorcontrib>Sugimoto, Isamu</creatorcontrib><creatorcontrib>Tanaka, Motoyuki</creatorcontrib><creatorcontrib>Takizawa, Hiroya</creatorcontrib><creatorcontrib>Yoshikawa, Ken</creatorcontrib><creatorcontrib>Sato, Kazutoyo</creatorcontrib><creatorcontrib>Narita, Masami</creatorcontrib><creatorcontrib>Ohuchida, Shuichi</creatorcontrib><creatorcontrib>Nakai, Hisao</creatorcontrib><creatorcontrib>Toda, Masaaki</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><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Asada, Masaki</au><au>Obitsu, Tetsuo</au><au>Kinoshita, Atsushi</au><au>Nakai, Yoshihiko</au><au>Nagase, Toshihiko</au><au>Sugimoto, Isamu</au><au>Tanaka, Motoyuki</au><au>Takizawa, Hiroya</au><au>Yoshikawa, Ken</au><au>Sato, Kazutoyo</au><au>Narita, Masami</au><au>Ohuchida, Shuichi</au><au>Nakai, Hisao</au><au>Toda, Masaaki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Discovery of novel N-acylsulfonamide analogs as potent and selective EP3 receptor antagonists</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2010-04-15</date><risdate>2010</risdate><volume>20</volume><issue>8</issue><spage>2639</spage><epage>2643</epage><pages>2639-2643</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Identification of novel
N-acyl 3,4-difluorobenzenesulfonamide analogs as potent and selective EP3 receptor antagonists and their in vivo efficacy with respect to the PGE
2-induced uterine contraction in pregnant rats are reported.
A series of novel
N-acylsulfonamide analogs were synthesized and evaluated for their binding affinity and antagonist activity for the EP3 receptor subtype. Representative compounds were also evaluated for their inhibitory effect on PGE
2-induced uterine contraction in pregnant rats. Among those tested, a series of
N-acylbenzenesulfonamide analogs were found to be more potent than the corresponding carboxylic acid analogs in both the in vitro and in vivo evaluations. The structure activity relationships (SAR) are also discussed.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>20346663</pmid><doi>10.1016/j.bmcl.2010.02.034</doi><tpages>5</tpages></addata></record> |
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| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2010-04, Vol.20 (8), p.2639-2643 |
| issn | 0960-894X 1464-3405 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_746156607 |
| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Animals Antagonist Biological and medical sciences Dinoprostone - pharmacology Drug Discovery EP3 receptor Female Medical sciences Miscellaneous N-Acyl (3,4-difluorobenzene)sulfonamide N-Acylsulfonamide Pharmacology. Drug treatments Pregnancy Prostaglandin Rats Receptors, Prostaglandin E - antagonists & inhibitors Receptors, Prostaglandin E, EP3 Subtype Structure-Activity Relationship Sulfonamides - chemistry Sulfonamides - pharmacology Uterine Contraction - drug effects |
| title | Discovery of novel N-acylsulfonamide analogs as potent and selective EP3 receptor antagonists |
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