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Discovery of novel phenylpyridone derivatives as potent and selective MCH1R antagonists
The synthesis and evaluation of a series of phenylpyridone derivatives as MCH1R antagonists are described. The design, synthesis and structure–activity relationships of a novel class of N-phenylpyridone MCH1R antagonists are described. The core part of the N-phenylpyridone structure was newly design...
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| Published in: | Bioorganic & medicinal chemistry 2011-01, Vol.19 (2), p.883-893 |
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| Main Authors: | , , , , , , , , , , , , , |
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| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c438t-3e7247170a0242d1e0b0bf8857b9546aad9e3860e73af05227ac7308f28ef3333 |
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| cites | cdi_FETCH-LOGICAL-c438t-3e7247170a0242d1e0b0bf8857b9546aad9e3860e73af05227ac7308f28ef3333 |
| container_end_page | 893 |
| container_issue | 2 |
| container_start_page | 883 |
| container_title | Bioorganic & medicinal chemistry |
| container_volume | 19 |
| creator | Haga, Yuji Mizutani, Sayaka Naya, Akira Kishino, Hiroyuki Iwaasa, Hisashi Ito, Masahiko Ito, Junko Moriya, Minoru Sato, Nagaaki Takenaga, Norihiro Ishihara, Akane Tokita, Shigeru Kanatani, Akio Ohtake, Norikazu |
| description | The synthesis and evaluation of a series of phenylpyridone derivatives as MCH1R antagonists are described.
The design, synthesis and structure–activity relationships of a novel class of
N-phenylpyridone MCH1R antagonists are described. The core part of the
N-phenylpyridone structure was newly designed and the side chain moieties that were attached to the core part were extensively explored. As a result of optimization of the
N-phenylpyridone leads, we successfully developed the orally available, and brain-penetrable MCH1R selective antagonist
7c, exhibiting excellent anti-obese effect in diet-induced obese (DIO) mice. |
| doi_str_mv | 10.1016/j.bmc.2010.12.002 |
| format | article |
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The design, synthesis and structure–activity relationships of a novel class of
N-phenylpyridone MCH1R antagonists are described. The core part of the
N-phenylpyridone structure was newly designed and the side chain moieties that were attached to the core part were extensively explored. As a result of optimization of the
N-phenylpyridone leads, we successfully developed the orally available, and brain-penetrable MCH1R selective antagonist
7c, exhibiting excellent anti-obese effect in diet-induced obese (DIO) mice.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2010.12.002</identifier><identifier>PMID: 21190859</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Animals ; antagonists ; Anti-obesity ; Biological and medical sciences ; Drug Evaluation, Preclinical ; General and cellular metabolism. Vitamins ; Hormones. Endocrine system ; Humans ; MCH1R antagonist ; Medical sciences ; Melanin-concentrating hormone ; Mice ; Mice, Obese ; N-Phenylpyridone ; Pharmacology. Drug treatments ; Pyridones - chemical synthesis ; Pyridones - chemistry ; Pyridones - pharmacokinetics ; Rats ; Receptors, Somatostatin - antagonists & inhibitors ; Receptors, Somatostatin - metabolism ; Structure-Activity Relationship ; structure-activity relationships</subject><ispartof>Bioorganic & medicinal chemistry, 2011-01, Vol.19 (2), p.883-893</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2010 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c438t-3e7247170a0242d1e0b0bf8857b9546aad9e3860e73af05227ac7308f28ef3333</citedby><cites>FETCH-LOGICAL-c438t-3e7247170a0242d1e0b0bf8857b9546aad9e3860e73af05227ac7308f28ef3333</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=23835431$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21190859$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Haga, Yuji</creatorcontrib><creatorcontrib>Mizutani, Sayaka</creatorcontrib><creatorcontrib>Naya, Akira</creatorcontrib><creatorcontrib>Kishino, Hiroyuki</creatorcontrib><creatorcontrib>Iwaasa, Hisashi</creatorcontrib><creatorcontrib>Ito, Masahiko</creatorcontrib><creatorcontrib>Ito, Junko</creatorcontrib><creatorcontrib>Moriya, Minoru</creatorcontrib><creatorcontrib>Sato, Nagaaki</creatorcontrib><creatorcontrib>Takenaga, Norihiro</creatorcontrib><creatorcontrib>Ishihara, Akane</creatorcontrib><creatorcontrib>Tokita, Shigeru</creatorcontrib><creatorcontrib>Kanatani, Akio</creatorcontrib><creatorcontrib>Ohtake, Norikazu</creatorcontrib><title>Discovery of novel phenylpyridone derivatives as potent and selective MCH1R antagonists</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>The synthesis and evaluation of a series of phenylpyridone derivatives as MCH1R antagonists are described.
The design, synthesis and structure–activity relationships of a novel class of
N-phenylpyridone MCH1R antagonists are described. The core part of the
N-phenylpyridone structure was newly designed and the side chain moieties that were attached to the core part were extensively explored. As a result of optimization of the
N-phenylpyridone leads, we successfully developed the orally available, and brain-penetrable MCH1R selective antagonist
7c, exhibiting excellent anti-obese effect in diet-induced obese (DIO) mice.</description><subject>Animals</subject><subject>antagonists</subject><subject>Anti-obesity</subject><subject>Biological and medical sciences</subject><subject>Drug Evaluation, Preclinical</subject><subject>General and cellular metabolism. Vitamins</subject><subject>Hormones. Endocrine system</subject><subject>Humans</subject><subject>MCH1R antagonist</subject><subject>Medical sciences</subject><subject>Melanin-concentrating hormone</subject><subject>Mice</subject><subject>Mice, Obese</subject><subject>N-Phenylpyridone</subject><subject>Pharmacology. Drug treatments</subject><subject>Pyridones - chemical synthesis</subject><subject>Pyridones - chemistry</subject><subject>Pyridones - pharmacokinetics</subject><subject>Rats</subject><subject>Receptors, Somatostatin - antagonists & inhibitors</subject><subject>Receptors, Somatostatin - metabolism</subject><subject>Structure-Activity Relationship</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><recordid>eNqNkcuO0zAUQC0EYjoDH8AGvEGsUu61ncQRK1QYBmkQEjBiaTnOzeAqjYOdVurf46gFdghv_Dr34WPGniGsEbB6vV23O7cWsOzFGkA8YCtUlSqkbPAhW0FT6QJ0U12wy5S2kAnV4GN2IRAb0GWzYt_f-eTCgeKRh56PeTXw6QeNx2E6Rt-FkXhH0R_s7A-UuE18CjONM7djxxMN5JYL_mlzg1_y2Wzvw-jTnJ6wR70dEj09z1fs7vr9t81Ncfv5w8fN29vCKannQlItVI012Nya6JCghbbXuqzbplSVtV1DUldAtbQ9lELU1tUSdC809TKPK_bqlHeK4eee0mx2-UE0DHaksE9GawkoNf4HqaRCFBIyiSfSxZBSpN5M0e9sPBoEs4g3W5PFm0W8QWGy1hzz_Jx93-6o-xPx23QGXp4Bm5wd-mhH59NfTmpZKomZe3HiehuMvY-ZufuaK5WQqzWiXIg3J4Ky14OnaJLzNDrqfMzfYbrg_9HoL86VqGY</recordid><startdate>20110115</startdate><enddate>20110115</enddate><creator>Haga, Yuji</creator><creator>Mizutani, Sayaka</creator><creator>Naya, Akira</creator><creator>Kishino, Hiroyuki</creator><creator>Iwaasa, Hisashi</creator><creator>Ito, Masahiko</creator><creator>Ito, Junko</creator><creator>Moriya, Minoru</creator><creator>Sato, Nagaaki</creator><creator>Takenaga, Norihiro</creator><creator>Ishihara, Akane</creator><creator>Tokita, Shigeru</creator><creator>Kanatani, Akio</creator><creator>Ohtake, Norikazu</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><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20110115</creationdate><title>Discovery of novel phenylpyridone derivatives as potent and selective MCH1R antagonists</title><author>Haga, Yuji ; Mizutani, Sayaka ; Naya, Akira ; Kishino, Hiroyuki ; Iwaasa, Hisashi ; Ito, Masahiko ; Ito, Junko ; Moriya, Minoru ; Sato, Nagaaki ; Takenaga, Norihiro ; Ishihara, Akane ; Tokita, Shigeru ; Kanatani, Akio ; Ohtake, Norikazu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c438t-3e7247170a0242d1e0b0bf8857b9546aad9e3860e73af05227ac7308f28ef3333</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Animals</topic><topic>antagonists</topic><topic>Anti-obesity</topic><topic>Biological and medical sciences</topic><topic>Drug Evaluation, Preclinical</topic><topic>General and cellular metabolism. Vitamins</topic><topic>Hormones. Endocrine system</topic><topic>Humans</topic><topic>MCH1R antagonist</topic><topic>Medical sciences</topic><topic>Melanin-concentrating hormone</topic><topic>Mice</topic><topic>Mice, Obese</topic><topic>N-Phenylpyridone</topic><topic>Pharmacology. 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The design, synthesis and structure–activity relationships of a novel class of
N-phenylpyridone MCH1R antagonists are described. The core part of the
N-phenylpyridone structure was newly designed and the side chain moieties that were attached to the core part were extensively explored. As a result of optimization of the
N-phenylpyridone leads, we successfully developed the orally available, and brain-penetrable MCH1R selective antagonist
7c, exhibiting excellent anti-obese effect in diet-induced obese (DIO) mice.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>21190859</pmid><doi>10.1016/j.bmc.2010.12.002</doi><tpages>11</tpages></addata></record> |
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| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2011-01, Vol.19 (2), p.883-893 |
| issn | 0968-0896 1464-3391 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_883013813 |
| source | Elsevier:Jisc Collections:Elsevier Read and Publish Agreement 2022-2024:Freedom Collection (Reading list) |
| subjects | Animals antagonists Anti-obesity Biological and medical sciences Drug Evaluation, Preclinical General and cellular metabolism. Vitamins Hormones. Endocrine system Humans MCH1R antagonist Medical sciences Melanin-concentrating hormone Mice Mice, Obese N-Phenylpyridone Pharmacology. Drug treatments Pyridones - chemical synthesis Pyridones - chemistry Pyridones - pharmacokinetics Rats Receptors, Somatostatin - antagonists & inhibitors Receptors, Somatostatin - metabolism Structure-Activity Relationship structure-activity relationships |
| title | Discovery of novel phenylpyridone derivatives as potent and selective MCH1R antagonists |
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