Discovery of selective indole-based prostaglandin D₂ receptor antagonist
A series of N-benzoyl-2-methylindole-3-acetic acids were synthesized and biologically evaluated as prostaglandin (PG) D₂ receptor antagonists. Some of the selected compounds significantly inhibited OVA-induced vascular permeability in guinea pig conjunctiva after oral dosing. Structure–activity rela...
Gespeichert in:
Veröffentlicht in: | Bioorganic & medicinal chemistry 2011-08, Vol.19 (15), p.4574-4588 |
---|---|
Hauptverfasser: | , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 4588 |
---|---|
container_issue | 15 |
container_start_page | 4574 |
container_title | Bioorganic & medicinal chemistry |
container_volume | 19 |
creator | Iwahashi, Maki Shimabukuro, Atsushi Onoda, Takahiro Matsunaga, Yoko Okada, Yutaka Matsumoto, Ryoji Nambu, Fumio Nakai, Hisao Toda, Masaaki |
description | A series of N-benzoyl-2-methylindole-3-acetic acids were synthesized and biologically evaluated as prostaglandin (PG) D₂ receptor antagonists. Some of the selected compounds significantly inhibited OVA-induced vascular permeability in guinea pig conjunctiva after oral dosing. Structure–activity relationship study is presented. |
doi_str_mv | 10.1016/j.bmc.2011.06.014 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_878278307</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>878278307</sourcerecordid><originalsourceid>FETCH-LOGICAL-c335t-51f618591ba3a7717030b1e3fd6d271026abb16d73f1c6f681420134d261cd7a3</originalsourceid><addsrcrecordid>eNpFkblOxDAQhi0EguV4ABpIg6gSZmzHTkq03EKiAGrL8YGyyiaLnUWi5VF5Egy7QOXC3xz_N4QcIhQIKM5mRTM3BQXEAkQByDfIBLngOWM1bpIJ1KLKoarFDtmNcQYAlNe4TXYoSiZpVU7I3UUbzfDmwns2-Cy6zpmxfXNZ29uhc3mjo7PZIgxx1C-d7m3bZxefHx9ZcMYtxiFkuk8_Q9_GcZ9sed1Fd7B-98jz1eXT9Ca_f7i-nZ7f54axcsxL9AKrssZGMy0lSmDQoGPeCkslAhW6aVBYyTwa4UWFPCVk3FKBxkrN9sjpqm9a63Xp4qjmKYPr0npuWEZVyYrKioFMJK5IkwLE4LxahHauw7tCUN8G1Uwlg-rboAKhksFUc7Tuvmzmzv5V_CpLwMka0NHozgfdmzb-c5wj5T_Dj1ec14PSLyExz49pUgmA6TAM2BdiHIMf</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>878278307</pqid></control><display><type>article</type><title>Discovery of selective indole-based prostaglandin D₂ receptor antagonist</title><source>MEDLINE</source><source>Elsevier ScienceDirect Journals</source><creator>Iwahashi, Maki ; Shimabukuro, Atsushi ; Onoda, Takahiro ; Matsunaga, Yoko ; Okada, Yutaka ; Matsumoto, Ryoji ; Nambu, Fumio ; Nakai, Hisao ; Toda, Masaaki</creator><creatorcontrib>Iwahashi, Maki ; Shimabukuro, Atsushi ; Onoda, Takahiro ; Matsunaga, Yoko ; Okada, Yutaka ; Matsumoto, Ryoji ; Nambu, Fumio ; Nakai, Hisao ; Toda, Masaaki</creatorcontrib><description>A series of N-benzoyl-2-methylindole-3-acetic acids were synthesized and biologically evaluated as prostaglandin (PG) D₂ receptor antagonists. Some of the selected compounds significantly inhibited OVA-induced vascular permeability in guinea pig conjunctiva after oral dosing. Structure–activity relationship study is presented.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2011.06.014</identifier><identifier>PMID: 21737285</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Animals ; antagonists ; Biological and medical sciences ; Capillary Permeability - drug effects ; CHO Cells ; conjunctiva ; Conjunctiva - blood supply ; Cricetinae ; Cricetulus ; Drug Discovery ; Guinea Pigs ; Histamine and antagonists. Allergy ; Humans ; Indoles - chemistry ; Indoles - pharmacology ; Medical sciences ; permeability ; Pharmacology. Drug treatments ; prostaglandins ; Receptors, Immunologic - antagonists & inhibitors ; Receptors, Immunologic - metabolism ; Receptors, Prostaglandin - antagonists & inhibitors ; Receptors, Prostaglandin - metabolism ; structure-activity relationships</subject><ispartof>Bioorganic & medicinal chemistry, 2011-08, Vol.19 (15), p.4574-4588</ispartof><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c335t-51f618591ba3a7717030b1e3fd6d271026abb16d73f1c6f681420134d261cd7a3</citedby><cites>FETCH-LOGICAL-c335t-51f618591ba3a7717030b1e3fd6d271026abb16d73f1c6f681420134d261cd7a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24412407$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21737285$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Iwahashi, Maki</creatorcontrib><creatorcontrib>Shimabukuro, Atsushi</creatorcontrib><creatorcontrib>Onoda, Takahiro</creatorcontrib><creatorcontrib>Matsunaga, Yoko</creatorcontrib><creatorcontrib>Okada, Yutaka</creatorcontrib><creatorcontrib>Matsumoto, Ryoji</creatorcontrib><creatorcontrib>Nambu, Fumio</creatorcontrib><creatorcontrib>Nakai, Hisao</creatorcontrib><creatorcontrib>Toda, Masaaki</creatorcontrib><title>Discovery of selective indole-based prostaglandin D₂ receptor antagonist</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A series of N-benzoyl-2-methylindole-3-acetic acids were synthesized and biologically evaluated as prostaglandin (PG) D₂ receptor antagonists. Some of the selected compounds significantly inhibited OVA-induced vascular permeability in guinea pig conjunctiva after oral dosing. Structure–activity relationship study is presented.</description><subject>Animals</subject><subject>antagonists</subject><subject>Biological and medical sciences</subject><subject>Capillary Permeability - drug effects</subject><subject>CHO Cells</subject><subject>conjunctiva</subject><subject>Conjunctiva - blood supply</subject><subject>Cricetinae</subject><subject>Cricetulus</subject><subject>Drug Discovery</subject><subject>Guinea Pigs</subject><subject>Histamine and antagonists. Allergy</subject><subject>Humans</subject><subject>Indoles - chemistry</subject><subject>Indoles - pharmacology</subject><subject>Medical sciences</subject><subject>permeability</subject><subject>Pharmacology. Drug treatments</subject><subject>prostaglandins</subject><subject>Receptors, Immunologic - antagonists & inhibitors</subject><subject>Receptors, Immunologic - metabolism</subject><subject>Receptors, Prostaglandin - antagonists & inhibitors</subject><subject>Receptors, Prostaglandin - metabolism</subject><subject>structure-activity relationships</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkblOxDAQhi0EguV4ABpIg6gSZmzHTkq03EKiAGrL8YGyyiaLnUWi5VF5Egy7QOXC3xz_N4QcIhQIKM5mRTM3BQXEAkQByDfIBLngOWM1bpIJ1KLKoarFDtmNcQYAlNe4TXYoSiZpVU7I3UUbzfDmwns2-Cy6zpmxfXNZ29uhc3mjo7PZIgxx1C-d7m3bZxefHx9ZcMYtxiFkuk8_Q9_GcZ9sed1Fd7B-98jz1eXT9Ca_f7i-nZ7f54axcsxL9AKrssZGMy0lSmDQoGPeCkslAhW6aVBYyTwa4UWFPCVk3FKBxkrN9sjpqm9a63Xp4qjmKYPr0npuWEZVyYrKioFMJK5IkwLE4LxahHauw7tCUN8G1Uwlg-rboAKhksFUc7Tuvmzmzv5V_CpLwMka0NHozgfdmzb-c5wj5T_Dj1ec14PSLyExz49pUgmA6TAM2BdiHIMf</recordid><startdate>20110801</startdate><enddate>20110801</enddate><creator>Iwahashi, Maki</creator><creator>Shimabukuro, Atsushi</creator><creator>Onoda, Takahiro</creator><creator>Matsunaga, Yoko</creator><creator>Okada, Yutaka</creator><creator>Matsumoto, Ryoji</creator><creator>Nambu, Fumio</creator><creator>Nakai, Hisao</creator><creator>Toda, Masaaki</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>FBQ</scope><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>20110801</creationdate><title>Discovery of selective indole-based prostaglandin D₂ receptor antagonist</title><author>Iwahashi, Maki ; Shimabukuro, Atsushi ; Onoda, Takahiro ; Matsunaga, Yoko ; Okada, Yutaka ; Matsumoto, Ryoji ; Nambu, Fumio ; Nakai, Hisao ; Toda, Masaaki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c335t-51f618591ba3a7717030b1e3fd6d271026abb16d73f1c6f681420134d261cd7a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Animals</topic><topic>antagonists</topic><topic>Biological and medical sciences</topic><topic>Capillary Permeability - drug effects</topic><topic>CHO Cells</topic><topic>conjunctiva</topic><topic>Conjunctiva - blood supply</topic><topic>Cricetinae</topic><topic>Cricetulus</topic><topic>Drug Discovery</topic><topic>Guinea Pigs</topic><topic>Histamine and antagonists. Allergy</topic><topic>Humans</topic><topic>Indoles - chemistry</topic><topic>Indoles - pharmacology</topic><topic>Medical sciences</topic><topic>permeability</topic><topic>Pharmacology. Drug treatments</topic><topic>prostaglandins</topic><topic>Receptors, Immunologic - antagonists & inhibitors</topic><topic>Receptors, Immunologic - metabolism</topic><topic>Receptors, Prostaglandin - antagonists & inhibitors</topic><topic>Receptors, Prostaglandin - metabolism</topic><topic>structure-activity relationships</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Iwahashi, Maki</creatorcontrib><creatorcontrib>Shimabukuro, Atsushi</creatorcontrib><creatorcontrib>Onoda, Takahiro</creatorcontrib><creatorcontrib>Matsunaga, Yoko</creatorcontrib><creatorcontrib>Okada, Yutaka</creatorcontrib><creatorcontrib>Matsumoto, Ryoji</creatorcontrib><creatorcontrib>Nambu, Fumio</creatorcontrib><creatorcontrib>Nakai, Hisao</creatorcontrib><creatorcontrib>Toda, Masaaki</creatorcontrib><collection>AGRIS</collection><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>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Iwahashi, Maki</au><au>Shimabukuro, Atsushi</au><au>Onoda, Takahiro</au><au>Matsunaga, Yoko</au><au>Okada, Yutaka</au><au>Matsumoto, Ryoji</au><au>Nambu, Fumio</au><au>Nakai, Hisao</au><au>Toda, Masaaki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Discovery of selective indole-based prostaglandin D₂ receptor antagonist</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2011-08-01</date><risdate>2011</risdate><volume>19</volume><issue>15</issue><spage>4574</spage><epage>4588</epage><pages>4574-4588</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A series of N-benzoyl-2-methylindole-3-acetic acids were synthesized and biologically evaluated as prostaglandin (PG) D₂ receptor antagonists. Some of the selected compounds significantly inhibited OVA-induced vascular permeability in guinea pig conjunctiva after oral dosing. Structure–activity relationship study is presented.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>21737285</pmid><doi>10.1016/j.bmc.2011.06.014</doi><tpages>15</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0968-0896 |
ispartof | Bioorganic & medicinal chemistry, 2011-08, Vol.19 (15), p.4574-4588 |
issn | 0968-0896 1464-3391 |
language | eng |
recordid | cdi_proquest_miscellaneous_878278307 |
source | MEDLINE; Elsevier ScienceDirect Journals |
subjects | Animals antagonists Biological and medical sciences Capillary Permeability - drug effects CHO Cells conjunctiva Conjunctiva - blood supply Cricetinae Cricetulus Drug Discovery Guinea Pigs Histamine and antagonists. Allergy Humans Indoles - chemistry Indoles - pharmacology Medical sciences permeability Pharmacology. Drug treatments prostaglandins Receptors, Immunologic - antagonists & inhibitors Receptors, Immunologic - metabolism Receptors, Prostaglandin - antagonists & inhibitors Receptors, Prostaglandin - metabolism structure-activity relationships |
title | Discovery of selective indole-based prostaglandin D₂ receptor antagonist |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-08T08%3A22%3A49IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Discovery%20of%20selective%20indole-based%20prostaglandin%20D%E2%82%82%20receptor%20antagonist&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry&rft.au=Iwahashi,%20Maki&rft.date=2011-08-01&rft.volume=19&rft.issue=15&rft.spage=4574&rft.epage=4588&rft.pages=4574-4588&rft.issn=0968-0896&rft.eissn=1464-3391&rft_id=info:doi/10.1016/j.bmc.2011.06.014&rft_dat=%3Cproquest_cross%3E878278307%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=878278307&rft_id=info:pmid/21737285&rfr_iscdi=true |