Design and synthesis of substituted quinolines as novel and selective melanin concentrating hormone antagonists as anti-obesity agents
A novel series of substituted quinoline analogs were designed and synthesized as potent and selective melanin concentrating hormone (MCH) antagonists. These analogs show potent (nM) activity ( 12a– k) with a moderate selectivity. Conversely, the conformationally constrained thienopyrimidinone analog...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2006-10, Vol.16 (19), p.5207-5211 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Warshakoon, Namal C. Sheville, Justin Bhatt, Ritu Tiku Ji, Wei Mendez-Andino, Jose L. Meyers, Kenneth M. Kim, Nick Wos, John A. Mitchell, Chrissy Paris, Jennifer L. Pinney, Beth B. Reizes, Ofer Hu, X. Eric |
| description | A novel series of substituted quinoline analogs were designed and synthesized as potent and selective melanin concentrating hormone (MCH) antagonists. These analogs show potent (nM) activity (
12a–
k) with a moderate selectivity. Conversely, the conformationally constrained thienopyrimidinone analogs (
18a–
g) showed improved activity in MCH-1R and selectivity over 5HT2C. |
| doi_str_mv | 10.1016/j.bmcl.2006.07.006 |
| format | Article |
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12a–
k) with a moderate selectivity. Conversely, the conformationally constrained thienopyrimidinone analogs (
18a–
g) showed improved activity in MCH-1R and selectivity over 5HT2C.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2006.07.006</identifier><identifier>PMID: 16870427</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Anti-obesity ; Anti-Obesity Agents - chemical synthesis ; Anti-Obesity Agents - pharmacology ; Biological and medical sciences ; Drug Design ; General and cellular metabolism. Vitamins ; Humans ; Hypothalamic Hormones - antagonists & inhibitors ; Inhibitory Concentration 50 ; Ligands ; Medical sciences ; Melanin concentrating hormone antagonists ; Melanins - antagonists & inhibitors ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Pharmacology. Drug treatments ; Pituitary Hormones - antagonists & inhibitors ; Pyrimidinones ; Quinolines ; Quinolines - chemical synthesis ; Quinolines - pharmacology ; Serotoninergic system ; Structure-Activity Relationship ; Substrate Specificity</subject><ispartof>Bioorganic & medicinal chemistry letters, 2006-10, Vol.16 (19), p.5207-5211</ispartof><rights>2006 Elsevier Ltd</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c481t-2352bcbe2bda3899ca83f7f4e7e9d6ae7052ae895f18efc4569b72ba1837a51d3</citedby><cites>FETCH-LOGICAL-c481t-2352bcbe2bda3899ca83f7f4e7e9d6ae7052ae895f18efc4569b72ba1837a51d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X06007785$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18066703$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16870427$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Warshakoon, Namal C.</creatorcontrib><creatorcontrib>Sheville, Justin</creatorcontrib><creatorcontrib>Bhatt, Ritu Tiku</creatorcontrib><creatorcontrib>Ji, Wei</creatorcontrib><creatorcontrib>Mendez-Andino, Jose L.</creatorcontrib><creatorcontrib>Meyers, Kenneth M.</creatorcontrib><creatorcontrib>Kim, Nick</creatorcontrib><creatorcontrib>Wos, John A.</creatorcontrib><creatorcontrib>Mitchell, Chrissy</creatorcontrib><creatorcontrib>Paris, Jennifer L.</creatorcontrib><creatorcontrib>Pinney, Beth B.</creatorcontrib><creatorcontrib>Reizes, Ofer</creatorcontrib><creatorcontrib>Hu, X. Eric</creatorcontrib><title>Design and synthesis of substituted quinolines as novel and selective melanin concentrating hormone antagonists as anti-obesity agents</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A novel series of substituted quinoline analogs were designed and synthesized as potent and selective melanin concentrating hormone (MCH) antagonists. These analogs show potent (nM) activity (
12a–
k) with a moderate selectivity. Conversely, the conformationally constrained thienopyrimidinone analogs (
18a–
g) showed improved activity in MCH-1R and selectivity over 5HT2C.</description><subject>Anti-obesity</subject><subject>Anti-Obesity Agents - chemical synthesis</subject><subject>Anti-Obesity Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Drug Design</subject><subject>General and cellular metabolism. Vitamins</subject><subject>Humans</subject><subject>Hypothalamic Hormones - antagonists & inhibitors</subject><subject>Inhibitory Concentration 50</subject><subject>Ligands</subject><subject>Medical sciences</subject><subject>Melanin concentrating hormone antagonists</subject><subject>Melanins - antagonists & inhibitors</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Pharmacology. Drug treatments</subject><subject>Pituitary Hormones - antagonists & inhibitors</subject><subject>Pyrimidinones</subject><subject>Quinolines</subject><subject>Quinolines - chemical synthesis</subject><subject>Quinolines - pharmacology</subject><subject>Serotoninergic system</subject><subject>Structure-Activity Relationship</subject><subject>Substrate Specificity</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1r3DAQhkVpabZp_0APRZf2ZkeyZcmGXkr6CYFcUuhNSPJ4o8WWEo28sH8gv7va7kJuPQ0Dz_vO8BDynrOaMy6vdrVd3Fw3jMmaqbqMF2TDhRRVK1j3kmzYIFnVD-LPBXmDuGOMCybEa3LBZa-YaNSGPH0F9NtATRgpHkK-LyvSOFFcLWaf1wwjfVx9iLMPgNQgDXEP8ykAM7js90AXmE3wgboYHIScTPZhS-9jWmKAwmazjcFj_ldQVl9FWy7lAzXbwuNb8moyM8K787wkv79_u7v-Wd3c_vh1_eWmcqLnuWrarrHOQmNH0_bD4EzfTmoSoGAYpQHFusZAP3QT72FyopODVY01vG-V6fjYXpJPp96HFB9XwKwXjw7m8j3EFTUfRCdYIwrYnECXImKCST8kv5h00Jzpo32900f7-mhfM6XLKKEP5_bVLjA-R866C_DxDBh0Zp6SCc7jM9czKRVrC_f5xEFxsfeQNDoPRe3oUzGux-j_98dfSBGnPw</recordid><startdate>20061001</startdate><enddate>20061001</enddate><creator>Warshakoon, Namal C.</creator><creator>Sheville, Justin</creator><creator>Bhatt, Ritu Tiku</creator><creator>Ji, Wei</creator><creator>Mendez-Andino, Jose L.</creator><creator>Meyers, Kenneth M.</creator><creator>Kim, Nick</creator><creator>Wos, John A.</creator><creator>Mitchell, Chrissy</creator><creator>Paris, Jennifer L.</creator><creator>Pinney, Beth B.</creator><creator>Reizes, Ofer</creator><creator>Hu, X. Eric</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>7QO</scope><scope>7TS</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>20061001</creationdate><title>Design and synthesis of substituted quinolines as novel and selective melanin concentrating hormone antagonists as anti-obesity agents</title><author>Warshakoon, Namal C. ; Sheville, Justin ; Bhatt, Ritu Tiku ; Ji, Wei ; Mendez-Andino, Jose L. ; Meyers, Kenneth M. ; Kim, Nick ; Wos, John A. ; Mitchell, Chrissy ; Paris, Jennifer L. ; Pinney, Beth B. ; Reizes, Ofer ; Hu, X. Eric</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c481t-2352bcbe2bda3899ca83f7f4e7e9d6ae7052ae895f18efc4569b72ba1837a51d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Anti-obesity</topic><topic>Anti-Obesity Agents - chemical synthesis</topic><topic>Anti-Obesity Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Drug Design</topic><topic>General and cellular metabolism. Vitamins</topic><topic>Humans</topic><topic>Hypothalamic Hormones - antagonists & inhibitors</topic><topic>Inhibitory Concentration 50</topic><topic>Ligands</topic><topic>Medical sciences</topic><topic>Melanin concentrating hormone antagonists</topic><topic>Melanins - antagonists & inhibitors</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Pharmacology. Drug treatments</topic><topic>Pituitary Hormones - antagonists & inhibitors</topic><topic>Pyrimidinones</topic><topic>Quinolines</topic><topic>Quinolines - chemical synthesis</topic><topic>Quinolines - pharmacology</topic><topic>Serotoninergic system</topic><topic>Structure-Activity Relationship</topic><topic>Substrate Specificity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Warshakoon, Namal C.</creatorcontrib><creatorcontrib>Sheville, Justin</creatorcontrib><creatorcontrib>Bhatt, Ritu Tiku</creatorcontrib><creatorcontrib>Ji, Wei</creatorcontrib><creatorcontrib>Mendez-Andino, Jose L.</creatorcontrib><creatorcontrib>Meyers, Kenneth M.</creatorcontrib><creatorcontrib>Kim, Nick</creatorcontrib><creatorcontrib>Wos, John A.</creatorcontrib><creatorcontrib>Mitchell, Chrissy</creatorcontrib><creatorcontrib>Paris, Jennifer L.</creatorcontrib><creatorcontrib>Pinney, Beth B.</creatorcontrib><creatorcontrib>Reizes, Ofer</creatorcontrib><creatorcontrib>Hu, X. 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Eric</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design and synthesis of substituted quinolines as novel and selective melanin concentrating hormone antagonists as anti-obesity agents</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2006-10-01</date><risdate>2006</risdate><volume>16</volume><issue>19</issue><spage>5207</spage><epage>5211</epage><pages>5207-5211</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>A novel series of substituted quinoline analogs were designed and synthesized as potent and selective melanin concentrating hormone (MCH) antagonists. These analogs show potent (nM) activity (
12a–
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18a–
g) showed improved activity in MCH-1R and selectivity over 5HT2C.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16870427</pmid><doi>10.1016/j.bmcl.2006.07.006</doi><tpages>5</tpages></addata></record> |
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| subjects | Anti-obesity Anti-Obesity Agents - chemical synthesis Anti-Obesity Agents - pharmacology Biological and medical sciences Drug Design General and cellular metabolism. Vitamins Humans Hypothalamic Hormones - antagonists & inhibitors Inhibitory Concentration 50 Ligands Medical sciences Melanin concentrating hormone antagonists Melanins - antagonists & inhibitors Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Pharmacology. Drug treatments Pituitary Hormones - antagonists & inhibitors Pyrimidinones Quinolines Quinolines - chemical synthesis Quinolines - pharmacology Serotoninergic system Structure-Activity Relationship Substrate Specificity |
| title | Design and synthesis of substituted quinolines as novel and selective melanin concentrating hormone antagonists as anti-obesity agents |
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