New μ-Opioid Receptor Agonists with Piperazine Moiety
New μ-opioid receptor (MOR) agonists containing piperazine and homopiperazine moieties in the structures were synthesized and their affinities to and agonist potencies on MOR were evaluated. Among the synthesized compounds, 4-[4-(2-methoxyphenyl)piperazin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide (2...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 2001, Vol.49(10), pp.1314-1320 |
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| container_issue | 10 |
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| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 49 |
| creator | KOMOTO, Teruo OKADA, Tomomi SATO, Susumu NIINO, Yasuhiro OKA, Tetsuo SAKAMOTO, Takao |
| description | New μ-opioid receptor (MOR) agonists containing piperazine and homopiperazine moieties in the structures were synthesized and their affinities to and agonist potencies on MOR were evaluated. Among the synthesized compounds, 4-[4-(2-methoxyphenyl)piperazin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide (20Aa) showed the highest affinity to the human MOR expressed in Chinese hamster ovary (CHO)-K1 cells, and the highest agonist potency on the MOR in isolated guinea-pig ileum preparation. |
| doi_str_mv | 10.1248/cpb.49.1314 |
| format | Article |
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Among the synthesized compounds, 4-[4-(2-methoxyphenyl)piperazin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide (20Aa) showed the highest affinity to the human MOR expressed in Chinese hamster ovary (CHO)-K1 cells, and the highest agonist potency on the MOR in isolated guinea-pig ileum preparation.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.49.1314</identifier><identifier>PMID: 11605661</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>Animals ; Biological and medical sciences ; CHO Cells ; Cricetinae ; cross-coupling ; Enkephalin, Ala-MePhe-Gly- - pharmacology ; Guinea Pigs ; Humans ; Ileum - drug effects ; In Vitro Techniques ; Indicators and Reagents ; Magnetic Resonance Spectroscopy ; Male ; Mass Spectrometry ; Medical sciences ; Muscle, Smooth - drug effects ; Neuropharmacology ; Neurotransmitters. Neurotransmission. Receptors ; Pd-catalyzed amination ; Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems ; Pharmacology. Drug treatments ; piperazine ; Piperazines - chemical synthesis ; Piperazines - chemistry ; Piperazines - pharmacology ; Receptors, Opioid, kappa - antagonists & inhibitors ; Receptors, Opioid, mu - agonists ; Spectrophotometry, Infrared ; μ-opioid receptor agonist</subject><ispartof>Chemical and Pharmaceutical Bulletin, 2001, Vol.49(10), pp.1314-1320</ispartof><rights>2001 The Pharmaceutical Society of Japan</rights><rights>2002 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c464t-170595a2ca4f2223f56ce802aea569562cab0823b53fa98222f943e699fde5b53</citedby><cites>FETCH-LOGICAL-c464t-170595a2ca4f2223f56ce802aea569562cab0823b53fa98222f943e699fde5b53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,1883,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14102146$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11605661$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>KOMOTO, Teruo</creatorcontrib><creatorcontrib>OKADA, Tomomi</creatorcontrib><creatorcontrib>SATO, Susumu</creatorcontrib><creatorcontrib>NIINO, Yasuhiro</creatorcontrib><creatorcontrib>OKA, Tetsuo</creatorcontrib><creatorcontrib>SAKAMOTO, Takao</creatorcontrib><title>New μ-Opioid Receptor Agonists with Piperazine Moiety</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>New μ-opioid receptor (MOR) agonists containing piperazine and homopiperazine moieties in the structures were synthesized and their affinities to and agonist potencies on MOR were evaluated. Among the synthesized compounds, 4-[4-(2-methoxyphenyl)piperazin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide (20Aa) showed the highest affinity to the human MOR expressed in Chinese hamster ovary (CHO)-K1 cells, and the highest agonist potency on the MOR in isolated guinea-pig ileum preparation.</description><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>CHO Cells</subject><subject>Cricetinae</subject><subject>cross-coupling</subject><subject>Enkephalin, Ala-MePhe-Gly- - pharmacology</subject><subject>Guinea Pigs</subject><subject>Humans</subject><subject>Ileum - drug effects</subject><subject>In Vitro Techniques</subject><subject>Indicators and Reagents</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Male</subject><subject>Mass Spectrometry</subject><subject>Medical sciences</subject><subject>Muscle, Smooth - drug effects</subject><subject>Neuropharmacology</subject><subject>Neurotransmitters. Neurotransmission. Receptors</subject><subject>Pd-catalyzed amination</subject><subject>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</subject><subject>Pharmacology. Drug treatments</subject><subject>piperazine</subject><subject>Piperazines - chemical synthesis</subject><subject>Piperazines - chemistry</subject><subject>Piperazines - pharmacology</subject><subject>Receptors, Opioid, kappa - antagonists & inhibitors</subject><subject>Receptors, Opioid, mu - agonists</subject><subject>Spectrophotometry, Infrared</subject><subject>μ-opioid receptor agonist</subject><issn>0009-2363</issn><issn>1347-5223</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpF0EtLAzEQB_AgitbHybvsRS-yNe_dHGvxBb4QPYc0ndWU7e6apBT9bH4GP5MpXexlAjM_ZsIfoWOCh4Ty8sJ2kyFXQ8II30IDwniRC0rZNhpgjFVOmWR7aD-EGcZU4ILtoj1CJBZSkgGSj7DMfn_yp861bpq9gIUutj4bvbeNCzFkSxc_smfXgTffroHsoXUQvw7RTmXqAEf9e4Derq9ex7f5_dPN3Xh0n1suecxJgYUShlrDK5r-VAlpocTUgBFSCZkGE1xSNhGsMqpMpFKcgVSqmoJI3QN0tt7b-fZzASHquQsW6to00C6CLijFpShYgudraH0bgodKd97Njf_SBOtVTDrFpLnSq5iSPunXLiZzmG5sn0sCpz0wwZq68qaxLmwcJ5gSLpO7XLtZiOYd_oHx0dka_o_ivq6ub4Yfxmto2B_oZoZw</recordid><startdate>20011001</startdate><enddate>20011001</enddate><creator>KOMOTO, Teruo</creator><creator>OKADA, Tomomi</creator><creator>SATO, Susumu</creator><creator>NIINO, Yasuhiro</creator><creator>OKA, Tetsuo</creator><creator>SAKAMOTO, Takao</creator><general>The Pharmaceutical Society of Japan</general><general>Maruzen</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></search><sort><creationdate>20011001</creationdate><title>New μ-Opioid Receptor Agonists with Piperazine Moiety</title><author>KOMOTO, Teruo ; OKADA, Tomomi ; SATO, Susumu ; NIINO, Yasuhiro ; OKA, Tetsuo ; SAKAMOTO, Takao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c464t-170595a2ca4f2223f56ce802aea569562cab0823b53fa98222f943e699fde5b53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>CHO Cells</topic><topic>Cricetinae</topic><topic>cross-coupling</topic><topic>Enkephalin, Ala-MePhe-Gly- - pharmacology</topic><topic>Guinea Pigs</topic><topic>Humans</topic><topic>Ileum - drug effects</topic><topic>In Vitro Techniques</topic><topic>Indicators and Reagents</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Male</topic><topic>Mass Spectrometry</topic><topic>Medical sciences</topic><topic>Muscle, Smooth - drug effects</topic><topic>Neuropharmacology</topic><topic>Neurotransmitters. Neurotransmission. Receptors</topic><topic>Pd-catalyzed amination</topic><topic>Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems</topic><topic>Pharmacology. Drug treatments</topic><topic>piperazine</topic><topic>Piperazines - chemical synthesis</topic><topic>Piperazines - chemistry</topic><topic>Piperazines - pharmacology</topic><topic>Receptors, Opioid, kappa - antagonists & inhibitors</topic><topic>Receptors, Opioid, mu - agonists</topic><topic>Spectrophotometry, Infrared</topic><topic>μ-opioid receptor agonist</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>KOMOTO, Teruo</creatorcontrib><creatorcontrib>OKADA, Tomomi</creatorcontrib><creatorcontrib>SATO, Susumu</creatorcontrib><creatorcontrib>NIINO, Yasuhiro</creatorcontrib><creatorcontrib>OKA, Tetsuo</creatorcontrib><creatorcontrib>SAKAMOTO, Takao</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><jtitle>Chemical & pharmaceutical bulletin</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>KOMOTO, Teruo</au><au>OKADA, Tomomi</au><au>SATO, Susumu</au><au>NIINO, Yasuhiro</au><au>OKA, Tetsuo</au><au>SAKAMOTO, Takao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New μ-Opioid Receptor Agonists with Piperazine Moiety</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>2001-10-01</date><risdate>2001</risdate><volume>49</volume><issue>10</issue><spage>1314</spage><epage>1320</epage><pages>1314-1320</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>New μ-opioid receptor (MOR) agonists containing piperazine and homopiperazine moieties in the structures were synthesized and their affinities to and agonist potencies on MOR were evaluated. Among the synthesized compounds, 4-[4-(2-methoxyphenyl)piperazin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide (20Aa) showed the highest affinity to the human MOR expressed in Chinese hamster ovary (CHO)-K1 cells, and the highest agonist potency on the MOR in isolated guinea-pig ileum preparation.</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><pmid>11605661</pmid><doi>10.1248/cpb.49.1314</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| source | J-STAGE Free; MEDLINE; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Animals Biological and medical sciences CHO Cells Cricetinae cross-coupling Enkephalin, Ala-MePhe-Gly- - pharmacology Guinea Pigs Humans Ileum - drug effects In Vitro Techniques Indicators and Reagents Magnetic Resonance Spectroscopy Male Mass Spectrometry Medical sciences Muscle, Smooth - drug effects Neuropharmacology Neurotransmitters. Neurotransmission. Receptors Pd-catalyzed amination Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems Pharmacology. Drug treatments piperazine Piperazines - chemical synthesis Piperazines - chemistry Piperazines - pharmacology Receptors, Opioid, kappa - antagonists & inhibitors Receptors, Opioid, mu - agonists Spectrophotometry, Infrared μ-opioid receptor agonist |
| title | New μ-Opioid Receptor Agonists with Piperazine Moiety |
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