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1-Aryl-3-(4-pyridine-2-ylpiperazin-1-yl)propan-1-one Oximes as Potent Dopamine D4 Receptor Agonists for the Treatment of Erectile Dysfunction
A new series of dopamine D4 receptor agonists, 1-aryl-3-(4-pyridinepiperazin-1-yl)propanone oximes, was designed through the modification of known dopamine D4 receptor agonist PD 168077. Replacement of the amide group with a methylene-oxime moiety produced compounds with improved stability and effic...
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| Published in: | Journal of medicinal chemistry 2006-08, Vol.49 (17), p.5093-5109 |
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| Main Authors: | , , , , , , , , , , , , , , , , , , , , , , |
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| container_end_page | 5109 |
| container_issue | 17 |
| container_start_page | 5093 |
| container_title | Journal of medicinal chemistry |
| container_volume | 49 |
| creator | Kolasa, Teodozyj Matulenko, Mark A Hakeem, Ahmed A Patel, Meena V Mortell, Kathleen Bhatia, Pramila Henry, Rodger Nakane, Masaki Hsieh, Gin C Terranova, Marc A Uchic, Marie E Miller, Loan N Chang, Renje Donnelly-Roberts, Diana L Namovic, Marian T Hollingsworth, Peter R Martino, Brenda El Kouhen, Odile Marsh, Kennan C Wetter, Jill M Moreland, Robert B Brioni, Jorge D Stewart, Andrew O |
| description | A new series of dopamine D4 receptor agonists, 1-aryl-3-(4-pyridinepiperazin-1-yl)propanone oximes, was designed through the modification of known dopamine D4 receptor agonist PD 168077. Replacement of the amide group with a methylene-oxime moiety produced compounds with improved stability and efficacy. Structure−activity relationsips (SAR) of the aromatic ring linked to the N-4-piperazine ring confirmed the superiority of 2-pyridine as a core for D4 agonist activity. A two-methylene linker between the oxime group and the N-1-piperazine ring displayed the best profile. New dopamine D4 receptor agonists, exemplified by (E)-1-(4-chlorophenyl)-3-(4-pyridin-2-ylpiperazin-1-yl)propan-1-one O-methyloxime (59a) and (E)-1-(3-chloro-4-fluorophenyl)-3-(4-pyridin-2-ylpiperazin-1-yl)propan-1-one O-methyloxime (64a), exhibited favorable pharmacokinetic profiles and showed oral bioavailability in rat and dog. Subsequent evaluation of 59a in the rat penile erection model revealed in vivo activity, comparable in efficacy to apomorphine. Our results suggest that the oximes provide a novel structural linker for 4-arylpiperazine-based D4 agonists, possessing leadlike quality and with potential to develop a new class of potent and selective dopamine D4 receptor agonists. |
| doi_str_mv | 10.1021/jm060279f |
| format | article |
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Replacement of the amide group with a methylene-oxime moiety produced compounds with improved stability and efficacy. Structure−activity relationsips (SAR) of the aromatic ring linked to the N-4-piperazine ring confirmed the superiority of 2-pyridine as a core for D4 agonist activity. A two-methylene linker between the oxime group and the N-1-piperazine ring displayed the best profile. New dopamine D4 receptor agonists, exemplified by (E)-1-(4-chlorophenyl)-3-(4-pyridin-2-ylpiperazin-1-yl)propan-1-one O-methyloxime (59a) and (E)-1-(3-chloro-4-fluorophenyl)-3-(4-pyridin-2-ylpiperazin-1-yl)propan-1-one O-methyloxime (64a), exhibited favorable pharmacokinetic profiles and showed oral bioavailability in rat and dog. Subsequent evaluation of 59a in the rat penile erection model revealed in vivo activity, comparable in efficacy to apomorphine. Our results suggest that the oximes provide a novel structural linker for 4-arylpiperazine-based D4 agonists, possessing leadlike quality and with potential to develop a new class of potent and selective dopamine D4 receptor agonists.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm060279f</identifier><identifier>PMID: 16913699</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Benzamides - chemistry ; Benzamides - pharmacology ; Binding Sites ; Biological and medical sciences ; Cell Line ; Crystallography, X-Ray ; Disease Models, Animal ; Drug Evaluation, Preclinical ; Erectile Dysfunction - drug therapy ; Ferrets ; Genital system. Reproduction ; Humans ; Male ; Medical sciences ; Models, Molecular ; Molecular Structure ; Oximes - chemical synthesis ; Oximes - chemistry ; Oximes - pharmacology ; Pharmacology. Drug treatments ; Piperazines - chemical synthesis ; Piperazines - chemistry ; Piperazines - pharmacology ; Rats ; Rats, Wistar ; Receptors, Dopamine D4 - agonists ; Stereoisomerism ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 2006-08, Vol.49 (17), p.5093-5109</ispartof><rights>Copyright © 2006 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,786,790,27957,27958</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18042580$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16913699$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kolasa, Teodozyj</creatorcontrib><creatorcontrib>Matulenko, Mark A</creatorcontrib><creatorcontrib>Hakeem, Ahmed A</creatorcontrib><creatorcontrib>Patel, Meena V</creatorcontrib><creatorcontrib>Mortell, Kathleen</creatorcontrib><creatorcontrib>Bhatia, Pramila</creatorcontrib><creatorcontrib>Henry, Rodger</creatorcontrib><creatorcontrib>Nakane, Masaki</creatorcontrib><creatorcontrib>Hsieh, Gin C</creatorcontrib><creatorcontrib>Terranova, Marc A</creatorcontrib><creatorcontrib>Uchic, Marie E</creatorcontrib><creatorcontrib>Miller, Loan N</creatorcontrib><creatorcontrib>Chang, Renje</creatorcontrib><creatorcontrib>Donnelly-Roberts, Diana L</creatorcontrib><creatorcontrib>Namovic, Marian T</creatorcontrib><creatorcontrib>Hollingsworth, Peter R</creatorcontrib><creatorcontrib>Martino, Brenda</creatorcontrib><creatorcontrib>El Kouhen, Odile</creatorcontrib><creatorcontrib>Marsh, Kennan C</creatorcontrib><creatorcontrib>Wetter, Jill M</creatorcontrib><creatorcontrib>Moreland, Robert B</creatorcontrib><creatorcontrib>Brioni, Jorge D</creatorcontrib><creatorcontrib>Stewart, Andrew O</creatorcontrib><title>1-Aryl-3-(4-pyridine-2-ylpiperazin-1-yl)propan-1-one Oximes as Potent Dopamine D4 Receptor Agonists for the Treatment of Erectile Dysfunction</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>A new series of dopamine D4 receptor agonists, 1-aryl-3-(4-pyridinepiperazin-1-yl)propanone oximes, was designed through the modification of known dopamine D4 receptor agonist PD 168077. Replacement of the amide group with a methylene-oxime moiety produced compounds with improved stability and efficacy. Structure−activity relationsips (SAR) of the aromatic ring linked to the N-4-piperazine ring confirmed the superiority of 2-pyridine as a core for D4 agonist activity. A two-methylene linker between the oxime group and the N-1-piperazine ring displayed the best profile. New dopamine D4 receptor agonists, exemplified by (E)-1-(4-chlorophenyl)-3-(4-pyridin-2-ylpiperazin-1-yl)propan-1-one O-methyloxime (59a) and (E)-1-(3-chloro-4-fluorophenyl)-3-(4-pyridin-2-ylpiperazin-1-yl)propan-1-one O-methyloxime (64a), exhibited favorable pharmacokinetic profiles and showed oral bioavailability in rat and dog. Subsequent evaluation of 59a in the rat penile erection model revealed in vivo activity, comparable in efficacy to apomorphine. Our results suggest that the oximes provide a novel structural linker for 4-arylpiperazine-based D4 agonists, possessing leadlike quality and with potential to develop a new class of potent and selective dopamine D4 receptor agonists.</description><subject>Animals</subject><subject>Benzamides - chemistry</subject><subject>Benzamides - pharmacology</subject><subject>Binding Sites</subject><subject>Biological and medical sciences</subject><subject>Cell Line</subject><subject>Crystallography, X-Ray</subject><subject>Disease Models, Animal</subject><subject>Drug Evaluation, Preclinical</subject><subject>Erectile Dysfunction - drug therapy</subject><subject>Ferrets</subject><subject>Genital system. Reproduction</subject><subject>Humans</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Oximes - chemical synthesis</subject><subject>Oximes - chemistry</subject><subject>Oximes - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Piperazines - chemical synthesis</subject><subject>Piperazines - chemistry</subject><subject>Piperazines - pharmacology</subject><subject>Rats</subject><subject>Rats, Wistar</subject><subject>Receptors, Dopamine D4 - agonists</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNpFkctuFDEQRS0EIkNgwQ8gb0CwMPjR7cdylBeRIiXKDGwtT081eOh2N7ZbSvMP_HM8yiRZVZXqVEn3XoTeM_qVUc6-7XoqKVemfYEWrOaUVJpWL9GCUs4Jl1wcoTcp7SilgnHxGh0xaZiQxizQf0aWce6IIJ8rMs7Rb30AwsncjX6E6P75QFiZvoxxGN2-HwLg6zvfQ8Iu4ZshQ8j4tCz7colPK3wLDYx5iHj5awg-5YTbMuTfgNcRXO73_NDiswhN9l05mVM7hdIP4S161bouwbtDPUY_zs_WJ9_J1fXF5cnyijjOeSZOK6O1gVpzaRqmxUZJ0QKlRZ2ot6A2RshNwytjtKGGUVUxpZhoHatAbpU4Rp8e_hZVfydI2fY-NdB1LsAwJSu1qrmme_DDAZw2PWztGH3v4mwfDSzAxwPgUuO6NrrQ-PTMlSB4rWnhyANXDIG7p72Lf6xUQtV2fbOyplr9rMVKW_H81zXJ7oYphuKHZdTuA7dPgYt7XBSXaQ</recordid><startdate>20060824</startdate><enddate>20060824</enddate><creator>Kolasa, Teodozyj</creator><creator>Matulenko, Mark A</creator><creator>Hakeem, Ahmed A</creator><creator>Patel, Meena V</creator><creator>Mortell, Kathleen</creator><creator>Bhatia, Pramila</creator><creator>Henry, Rodger</creator><creator>Nakane, Masaki</creator><creator>Hsieh, Gin C</creator><creator>Terranova, Marc A</creator><creator>Uchic, Marie E</creator><creator>Miller, Loan N</creator><creator>Chang, Renje</creator><creator>Donnelly-Roberts, Diana L</creator><creator>Namovic, Marian T</creator><creator>Hollingsworth, Peter R</creator><creator>Martino, Brenda</creator><creator>El Kouhen, Odile</creator><creator>Marsh, Kennan C</creator><creator>Wetter, Jill M</creator><creator>Moreland, Robert B</creator><creator>Brioni, Jorge D</creator><creator>Stewart, Andrew O</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20060824</creationdate><title>1-Aryl-3-(4-pyridine-2-ylpiperazin-1-yl)propan-1-one Oximes as Potent Dopamine D4 Receptor Agonists for the Treatment of Erectile Dysfunction</title><author>Kolasa, Teodozyj ; Matulenko, Mark A ; Hakeem, Ahmed A ; Patel, Meena V ; Mortell, Kathleen ; Bhatia, Pramila ; Henry, Rodger ; Nakane, Masaki ; Hsieh, Gin C ; Terranova, Marc A ; Uchic, Marie E ; Miller, Loan N ; Chang, Renje ; Donnelly-Roberts, Diana L ; Namovic, Marian T ; Hollingsworth, Peter R ; Martino, Brenda ; El Kouhen, Odile ; Marsh, Kennan C ; Wetter, Jill M ; Moreland, Robert B ; Brioni, Jorge D ; Stewart, Andrew O</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a222t-a879889e58269c183b763fe0012335de7b936bc24998909107417713fa14e6d73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Animals</topic><topic>Benzamides - chemistry</topic><topic>Benzamides - pharmacology</topic><topic>Binding Sites</topic><topic>Biological and medical sciences</topic><topic>Cell Line</topic><topic>Crystallography, X-Ray</topic><topic>Disease Models, Animal</topic><topic>Drug Evaluation, Preclinical</topic><topic>Erectile Dysfunction - drug therapy</topic><topic>Ferrets</topic><topic>Genital system. Reproduction</topic><topic>Humans</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Oximes - chemical synthesis</topic><topic>Oximes - chemistry</topic><topic>Oximes - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Piperazines - chemical synthesis</topic><topic>Piperazines - chemistry</topic><topic>Piperazines - pharmacology</topic><topic>Rats</topic><topic>Rats, Wistar</topic><topic>Receptors, Dopamine D4 - agonists</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kolasa, Teodozyj</creatorcontrib><creatorcontrib>Matulenko, Mark A</creatorcontrib><creatorcontrib>Hakeem, Ahmed A</creatorcontrib><creatorcontrib>Patel, Meena V</creatorcontrib><creatorcontrib>Mortell, Kathleen</creatorcontrib><creatorcontrib>Bhatia, Pramila</creatorcontrib><creatorcontrib>Henry, Rodger</creatorcontrib><creatorcontrib>Nakane, Masaki</creatorcontrib><creatorcontrib>Hsieh, Gin C</creatorcontrib><creatorcontrib>Terranova, Marc A</creatorcontrib><creatorcontrib>Uchic, Marie E</creatorcontrib><creatorcontrib>Miller, Loan N</creatorcontrib><creatorcontrib>Chang, Renje</creatorcontrib><creatorcontrib>Donnelly-Roberts, Diana L</creatorcontrib><creatorcontrib>Namovic, Marian T</creatorcontrib><creatorcontrib>Hollingsworth, Peter R</creatorcontrib><creatorcontrib>Martino, Brenda</creatorcontrib><creatorcontrib>El Kouhen, Odile</creatorcontrib><creatorcontrib>Marsh, Kennan C</creatorcontrib><creatorcontrib>Wetter, Jill M</creatorcontrib><creatorcontrib>Moreland, Robert B</creatorcontrib><creatorcontrib>Brioni, Jorge D</creatorcontrib><creatorcontrib>Stewart, Andrew O</creatorcontrib><collection>Istex</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>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kolasa, Teodozyj</au><au>Matulenko, Mark A</au><au>Hakeem, Ahmed A</au><au>Patel, Meena V</au><au>Mortell, Kathleen</au><au>Bhatia, Pramila</au><au>Henry, Rodger</au><au>Nakane, Masaki</au><au>Hsieh, Gin C</au><au>Terranova, Marc A</au><au>Uchic, Marie E</au><au>Miller, Loan N</au><au>Chang, Renje</au><au>Donnelly-Roberts, Diana L</au><au>Namovic, Marian T</au><au>Hollingsworth, Peter R</au><au>Martino, Brenda</au><au>El Kouhen, Odile</au><au>Marsh, Kennan C</au><au>Wetter, Jill M</au><au>Moreland, Robert B</au><au>Brioni, Jorge D</au><au>Stewart, Andrew O</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>1-Aryl-3-(4-pyridine-2-ylpiperazin-1-yl)propan-1-one Oximes as Potent Dopamine D4 Receptor Agonists for the Treatment of Erectile Dysfunction</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2006-08-24</date><risdate>2006</risdate><volume>49</volume><issue>17</issue><spage>5093</spage><epage>5109</epage><pages>5093-5109</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><notes>istex:45F14FB8F3DE143AC649281AE447A1C30A90443A</notes><notes>ark:/67375/TPS-94SV53S8-3</notes><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>A new series of dopamine D4 receptor agonists, 1-aryl-3-(4-pyridinepiperazin-1-yl)propanone oximes, was designed through the modification of known dopamine D4 receptor agonist PD 168077. Replacement of the amide group with a methylene-oxime moiety produced compounds with improved stability and efficacy. Structure−activity relationsips (SAR) of the aromatic ring linked to the N-4-piperazine ring confirmed the superiority of 2-pyridine as a core for D4 agonist activity. A two-methylene linker between the oxime group and the N-1-piperazine ring displayed the best profile. New dopamine D4 receptor agonists, exemplified by (E)-1-(4-chlorophenyl)-3-(4-pyridin-2-ylpiperazin-1-yl)propan-1-one O-methyloxime (59a) and (E)-1-(3-chloro-4-fluorophenyl)-3-(4-pyridin-2-ylpiperazin-1-yl)propan-1-one O-methyloxime (64a), exhibited favorable pharmacokinetic profiles and showed oral bioavailability in rat and dog. Subsequent evaluation of 59a in the rat penile erection model revealed in vivo activity, comparable in efficacy to apomorphine. Our results suggest that the oximes provide a novel structural linker for 4-arylpiperazine-based D4 agonists, possessing leadlike quality and with potential to develop a new class of potent and selective dopamine D4 receptor agonists.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16913699</pmid><doi>10.1021/jm060279f</doi><tpages>17</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 2006-08, Vol.49 (17), p.5093-5109 |
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| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Animals Benzamides - chemistry Benzamides - pharmacology Binding Sites Biological and medical sciences Cell Line Crystallography, X-Ray Disease Models, Animal Drug Evaluation, Preclinical Erectile Dysfunction - drug therapy Ferrets Genital system. Reproduction Humans Male Medical sciences Models, Molecular Molecular Structure Oximes - chemical synthesis Oximes - chemistry Oximes - pharmacology Pharmacology. Drug treatments Piperazines - chemical synthesis Piperazines - chemistry Piperazines - pharmacology Rats Rats, Wistar Receptors, Dopamine D4 - agonists Stereoisomerism Structure-Activity Relationship |
| title | 1-Aryl-3-(4-pyridine-2-ylpiperazin-1-yl)propan-1-one Oximes as Potent Dopamine D4 Receptor Agonists for the Treatment of Erectile Dysfunction |
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