Loading…
Potent and subtype-selective CCK-B/gastrin receptor antagonists: 2,4-dioxo-1,5-benzodiazepines with a plane of symmetry
A series of CCK-B/gastrin receptor antagonists, 2,4-dioxo-1,5-benzodiazepine derivatives with a plane of symmetry, were designed, synthesized, and evaluated for antagonistic activity. Structure-activity relationship studies revealed that carbonylmethyl groups at both N-1 and N-5 positions and hydrop...
Saved in:
| Published in: | Bioorganic & medicinal chemistry 1997-07, Vol.5 (7), p.1433-1446 |
|---|---|
| Main Authors: | , , , , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| Citations: | Items that this one cites Items that cite this one |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| cited_by | cdi_FETCH-LOGICAL-c360t-49ca2134aff5e3e4c11a619c9372e0b7f396e142cdbcc63c89af7b51bbbbeba3 |
|---|---|
| cites | cdi_FETCH-LOGICAL-c360t-49ca2134aff5e3e4c11a619c9372e0b7f396e142cdbcc63c89af7b51bbbbeba3 |
| container_end_page | 1446 |
| container_issue | 7 |
| container_start_page | 1433 |
| container_title | Bioorganic & medicinal chemistry |
| container_volume | 5 |
| creator | Hagishita, Sanji Seno, Kaoru Kamata, Susumu Haga, Nobuhiro Ishihara, Yasunobu Ishikawa, Michio Shimamura, Mayumi |
| description | A series of CCK-B/gastrin receptor antagonists, 2,4-dioxo-1,5-benzodiazepine derivatives with a plane of symmetry, were designed, synthesized, and evaluated for antagonistic activity. Structure-activity relationship studies revealed that carbonylmethyl groups at both
N-1 and
N-5 positions and hydrophilic groups, such as the carboxyl group on the benzene ring attached to the ureido group at the C-3 position, brought about potent affinity and subtype selectivity for CCK-B/gastrin receptors. Several compounds showed excellent in vivo inhibition of gastric acid secretion induced by pentagastrin in anesthetized rats.
Graphic |
| doi_str_mv | 10.1016/S0968-0896(97)00083-7 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_79390497</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0968089697000837</els_id><sourcerecordid>79390497</sourcerecordid><originalsourceid>FETCH-LOGICAL-c360t-49ca2134aff5e3e4c11a619c9372e0b7f396e142cdbcc63c89af7b51bbbbeba3</originalsourceid><addsrcrecordid>eNqFkEtLAzEQgIMotT5-QiEnUTCabNJN40W0-EJBwd5DNjurke5mTdJq_fVuH3h1LnOYb14fQgNGzxhl-fkrVfmI0JHKj5U8oZSOOJFbqM9ELgjnim2j_h-yi_Zi_OigTCjWQz3FpWSU99HXi0_QJGyaEsdZkRYtkAhTsMnNAY_Hj-T6_M3EFFyDA1hokw8dnMybb1xM8QJnp4KUzn97wk6HpIDmx5fO_EDrGoj4y6V3bHA7NQ1gX-G4qGtIYXGAdiozjXC4yftocnszGd-Tp-e7h_HVE7E8p4kIZU3GuDBVNQQOwjJmcqZsd38GtJAVVzkwkdmysDbndqRMJYshK7qAwvB9dLQe2wb_OYOYdO2ihenyHD-LWiquqFCyA4dr0AYfY4BKt8HVJiw0o3rpW69866VMraRe-dbLvsFmwayoofzr2gju6pfrOnRPzh0EHa2DxkLpOp1Jl979s-EX2PeRsw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>79390497</pqid></control><display><type>article</type><title>Potent and subtype-selective CCK-B/gastrin receptor antagonists: 2,4-dioxo-1,5-benzodiazepines with a plane of symmetry</title><source>Elsevier</source><creator>Hagishita, Sanji ; Seno, Kaoru ; Kamata, Susumu ; Haga, Nobuhiro ; Ishihara, Yasunobu ; Ishikawa, Michio ; Shimamura, Mayumi</creator><creatorcontrib>Hagishita, Sanji ; Seno, Kaoru ; Kamata, Susumu ; Haga, Nobuhiro ; Ishihara, Yasunobu ; Ishikawa, Michio ; Shimamura, Mayumi</creatorcontrib><description>A series of CCK-B/gastrin receptor antagonists, 2,4-dioxo-1,5-benzodiazepine derivatives with a plane of symmetry, were designed, synthesized, and evaluated for antagonistic activity. Structure-activity relationship studies revealed that carbonylmethyl groups at both
N-1 and
N-5 positions and hydrophilic groups, such as the carboxyl group on the benzene ring attached to the ureido group at the C-3 position, brought about potent affinity and subtype selectivity for CCK-B/gastrin receptors. Several compounds showed excellent in vivo inhibition of gastric acid secretion induced by pentagastrin in anesthetized rats.
Graphic</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/S0968-0896(97)00083-7</identifier><identifier>PMID: 9377103</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Animals ; Benzodiazepines - chemistry ; Benzodiazepines - metabolism ; Benzodiazepines - pharmacology ; Binding, Competitive ; Guinea Pigs ; Male ; Mice ; Mice, Inbred Strains ; Molecular Conformation ; Rats ; Rats, Sprague-Dawley ; Receptor, Cholecystokinin A ; Receptor, Cholecystokinin B ; Receptors, Cholecystokinin - antagonists & inhibitors ; Receptors, Cholecystokinin - metabolism ; Structure-Activity Relationship ; Substrate Specificity</subject><ispartof>Bioorganic & medicinal chemistry, 1997-07, Vol.5 (7), p.1433-1446</ispartof><rights>1997</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c360t-49ca2134aff5e3e4c11a619c9372e0b7f396e142cdbcc63c89af7b51bbbbeba3</citedby><cites>FETCH-LOGICAL-c360t-49ca2134aff5e3e4c11a619c9372e0b7f396e142cdbcc63c89af7b51bbbbeba3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9377103$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hagishita, Sanji</creatorcontrib><creatorcontrib>Seno, Kaoru</creatorcontrib><creatorcontrib>Kamata, Susumu</creatorcontrib><creatorcontrib>Haga, Nobuhiro</creatorcontrib><creatorcontrib>Ishihara, Yasunobu</creatorcontrib><creatorcontrib>Ishikawa, Michio</creatorcontrib><creatorcontrib>Shimamura, Mayumi</creatorcontrib><title>Potent and subtype-selective CCK-B/gastrin receptor antagonists: 2,4-dioxo-1,5-benzodiazepines with a plane of symmetry</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A series of CCK-B/gastrin receptor antagonists, 2,4-dioxo-1,5-benzodiazepine derivatives with a plane of symmetry, were designed, synthesized, and evaluated for antagonistic activity. Structure-activity relationship studies revealed that carbonylmethyl groups at both
N-1 and
N-5 positions and hydrophilic groups, such as the carboxyl group on the benzene ring attached to the ureido group at the C-3 position, brought about potent affinity and subtype selectivity for CCK-B/gastrin receptors. Several compounds showed excellent in vivo inhibition of gastric acid secretion induced by pentagastrin in anesthetized rats.
Graphic</description><subject>Animals</subject><subject>Benzodiazepines - chemistry</subject><subject>Benzodiazepines - metabolism</subject><subject>Benzodiazepines - pharmacology</subject><subject>Binding, Competitive</subject><subject>Guinea Pigs</subject><subject>Male</subject><subject>Mice</subject><subject>Mice, Inbred Strains</subject><subject>Molecular Conformation</subject><subject>Rats</subject><subject>Rats, Sprague-Dawley</subject><subject>Receptor, Cholecystokinin A</subject><subject>Receptor, Cholecystokinin B</subject><subject>Receptors, Cholecystokinin - antagonists & inhibitors</subject><subject>Receptors, Cholecystokinin - metabolism</subject><subject>Structure-Activity Relationship</subject><subject>Substrate Specificity</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1997</creationdate><recordtype>article</recordtype><recordid>eNqFkEtLAzEQgIMotT5-QiEnUTCabNJN40W0-EJBwd5DNjurke5mTdJq_fVuH3h1LnOYb14fQgNGzxhl-fkrVfmI0JHKj5U8oZSOOJFbqM9ELgjnim2j_h-yi_Zi_OigTCjWQz3FpWSU99HXi0_QJGyaEsdZkRYtkAhTsMnNAY_Hj-T6_M3EFFyDA1hokw8dnMybb1xM8QJnp4KUzn97wk6HpIDmx5fO_EDrGoj4y6V3bHA7NQ1gX-G4qGtIYXGAdiozjXC4yftocnszGd-Tp-e7h_HVE7E8p4kIZU3GuDBVNQQOwjJmcqZsd38GtJAVVzkwkdmysDbndqRMJYshK7qAwvB9dLQe2wb_OYOYdO2ihenyHD-LWiquqFCyA4dr0AYfY4BKt8HVJiw0o3rpW69866VMraRe-dbLvsFmwayoofzr2gju6pfrOnRPzh0EHa2DxkLpOp1Jl979s-EX2PeRsw</recordid><startdate>19970701</startdate><enddate>19970701</enddate><creator>Hagishita, Sanji</creator><creator>Seno, Kaoru</creator><creator>Kamata, Susumu</creator><creator>Haga, Nobuhiro</creator><creator>Ishihara, Yasunobu</creator><creator>Ishikawa, Michio</creator><creator>Shimamura, Mayumi</creator><general>Elsevier Ltd</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>19970701</creationdate><title>Potent and subtype-selective CCK-B/gastrin receptor antagonists: 2,4-dioxo-1,5-benzodiazepines with a plane of symmetry</title><author>Hagishita, Sanji ; Seno, Kaoru ; Kamata, Susumu ; Haga, Nobuhiro ; Ishihara, Yasunobu ; Ishikawa, Michio ; Shimamura, Mayumi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c360t-49ca2134aff5e3e4c11a619c9372e0b7f396e142cdbcc63c89af7b51bbbbeba3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><topic>Animals</topic><topic>Benzodiazepines - chemistry</topic><topic>Benzodiazepines - metabolism</topic><topic>Benzodiazepines - pharmacology</topic><topic>Binding, Competitive</topic><topic>Guinea Pigs</topic><topic>Male</topic><topic>Mice</topic><topic>Mice, Inbred Strains</topic><topic>Molecular Conformation</topic><topic>Rats</topic><topic>Rats, Sprague-Dawley</topic><topic>Receptor, Cholecystokinin A</topic><topic>Receptor, Cholecystokinin B</topic><topic>Receptors, Cholecystokinin - antagonists & inhibitors</topic><topic>Receptors, Cholecystokinin - metabolism</topic><topic>Structure-Activity Relationship</topic><topic>Substrate Specificity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hagishita, Sanji</creatorcontrib><creatorcontrib>Seno, Kaoru</creatorcontrib><creatorcontrib>Kamata, Susumu</creatorcontrib><creatorcontrib>Haga, Nobuhiro</creatorcontrib><creatorcontrib>Ishihara, Yasunobu</creatorcontrib><creatorcontrib>Ishikawa, Michio</creatorcontrib><creatorcontrib>Shimamura, Mayumi</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>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hagishita, Sanji</au><au>Seno, Kaoru</au><au>Kamata, Susumu</au><au>Haga, Nobuhiro</au><au>Ishihara, Yasunobu</au><au>Ishikawa, Michio</au><au>Shimamura, Mayumi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Potent and subtype-selective CCK-B/gastrin receptor antagonists: 2,4-dioxo-1,5-benzodiazepines with a plane of symmetry</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>1997-07-01</date><risdate>1997</risdate><volume>5</volume><issue>7</issue><spage>1433</spage><epage>1446</epage><pages>1433-1446</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A series of CCK-B/gastrin receptor antagonists, 2,4-dioxo-1,5-benzodiazepine derivatives with a plane of symmetry, were designed, synthesized, and evaluated for antagonistic activity. Structure-activity relationship studies revealed that carbonylmethyl groups at both
N-1 and
N-5 positions and hydrophilic groups, such as the carboxyl group on the benzene ring attached to the ureido group at the C-3 position, brought about potent affinity and subtype selectivity for CCK-B/gastrin receptors. Several compounds showed excellent in vivo inhibition of gastric acid secretion induced by pentagastrin in anesthetized rats.
Graphic</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>9377103</pmid><doi>10.1016/S0968-0896(97)00083-7</doi><tpages>14</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 1997-07, Vol.5 (7), p.1433-1446 |
| issn | 0968-0896 1464-3391 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_79390497 |
| source | Elsevier |
| subjects | Animals Benzodiazepines - chemistry Benzodiazepines - metabolism Benzodiazepines - pharmacology Binding, Competitive Guinea Pigs Male Mice Mice, Inbred Strains Molecular Conformation Rats Rats, Sprague-Dawley Receptor, Cholecystokinin A Receptor, Cholecystokinin B Receptors, Cholecystokinin - antagonists & inhibitors Receptors, Cholecystokinin - metabolism Structure-Activity Relationship Substrate Specificity |
| title | Potent and subtype-selective CCK-B/gastrin receptor antagonists: 2,4-dioxo-1,5-benzodiazepines with a plane of symmetry |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-04T15%3A35%3A56IST&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=Potent%20and%20subtype-selective%20CCK-B/gastrin%20receptor%20antagonists:%202,4-dioxo-1,5-benzodiazepines%20with%20a%20plane%20of%20symmetry&rft.jtitle=Bioorganic%20&%20medicinal%20chemistry&rft.au=Hagishita,%20Sanji&rft.date=1997-07-01&rft.volume=5&rft.issue=7&rft.spage=1433&rft.epage=1446&rft.pages=1433-1446&rft.issn=0968-0896&rft.eissn=1464-3391&rft_id=info:doi/10.1016/S0968-0896(97)00083-7&rft_dat=%3Cproquest_cross%3E79390497%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c360t-49ca2134aff5e3e4c11a619c9372e0b7f396e142cdbcc63c89af7b51bbbbeba3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=79390497&rft_id=info:pmid/9377103&rfr_iscdi=true |