Syntheses and Binding Studies of New [(Aryl)(aryloxy)methyl]piperidine Derivatives and Related Compounds as Potential Antidepressant Drugs with High Affinity for Serotonin (5-HT) and Norepinephrine (NE) Transporters
In a wide search program toward new, efficient, and fast-acting antidepressant drugs, we have prepared series of new compounds having an (aryl)(aryloxy)methyl moiety linked directly or through a methylene chain to different substituted and unsubstituted cycles (isoquinoline, piperazine, piperidine,...
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| Veröffentlicht in: | Journal of medicinal chemistry 2003-12, Vol.46 (25), p.5512-5532 |
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| container_title | Journal of medicinal chemistry |
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| creator | Orjales, Aurelio Mosquera, Ramón Toledo, Antonio Pumar, M. Carmen García, Neftalí Cortizo, Lourdes Labeaga, Luis Innerárity, Ana |
| description | In a wide search program toward new, efficient, and fast-acting antidepressant drugs, we have prepared series of new compounds having an (aryl)(aryloxy)methyl moiety linked directly or through a methylene chain to different substituted and unsubstituted cycles (isoquinoline, piperazine, piperidine, tetrahydropyran, or cyclopentane). These compounds have been evaluated for their affinities for serotonin (5-HT) transporter (SERT) and 5-HT1A and 5-HT2A receptors. Racemic mixtures of 4-[(aryl)(aryloxy)methyl]piperidine derivatives showed much higher affinity values for SERT than fluoxetine and resulted in lack of affinity for 5-HT1A and 5-HT2A receptors. Some of these racemic mixtures were resolved to their enantiomers and tested for binding to norepinephrine (NE) transporter (NET), dopamine (DA) transporter (DAT), and α2 receptor. Several of these enantiomers [( − )-15b, ( − )-15j, ( − )-15t, (+)-15u] displayed a dual binding profile with affinities for SERT and NET with K i < 25 nM and a NET/SERT ratio |
| doi_str_mv | 10.1021/jm0309349 |
| format | Article |
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Carmen ; García, Neftalí ; Cortizo, Lourdes ; Labeaga, Luis ; Innerárity, Ana</creator><creatorcontrib>Orjales, Aurelio ; Mosquera, Ramón ; Toledo, Antonio ; Pumar, M. Carmen ; García, Neftalí ; Cortizo, Lourdes ; Labeaga, Luis ; Innerárity, Ana</creatorcontrib><description>In a wide search program toward new, efficient, and fast-acting antidepressant drugs, we have prepared series of new compounds having an (aryl)(aryloxy)methyl moiety linked directly or through a methylene chain to different substituted and unsubstituted cycles (isoquinoline, piperazine, piperidine, tetrahydropyran, or cyclopentane). These compounds have been evaluated for their affinities for serotonin (5-HT) transporter (SERT) and 5-HT1A and 5-HT2A receptors. Racemic mixtures of 4-[(aryl)(aryloxy)methyl]piperidine derivatives showed much higher affinity values for SERT than fluoxetine and resulted in lack of affinity for 5-HT1A and 5-HT2A receptors. Some of these racemic mixtures were resolved to their enantiomers and tested for binding to norepinephrine (NE) transporter (NET), dopamine (DA) transporter (DAT), and α2 receptor. Several of these enantiomers [( − )-15b, ( − )-15j, ( − )-15t, (+)-15u] displayed a dual binding profile with affinities for SERT and NET with K i < 25 nM and a NET/SERT ratio <10. Compound ( − )-15j (coded as F-98214-TA for development studies) showed a dual binding profile with very high affinity values for SERT and NET (K i = 1.9 and 13.5 nM, respectively), and further pharmacological characterization is in progress for its evaluation as a antidepressant.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm0309349</identifier><identifier>PMID: 14640559</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Adrenergic Uptake Inhibitors - chemical synthesis ; Adrenergic Uptake Inhibitors - chemistry ; Adrenergic Uptake Inhibitors - pharmacology ; Animals ; Antidepressive Agents - chemical synthesis ; Antidepressive Agents - chemistry ; Antidepressive Agents - pharmacology ; Biological and medical sciences ; Brain - metabolism ; Carrier Proteins - metabolism ; Fluoxetine - analogs & derivatives ; Fluoxetine - chemistry ; In Vitro Techniques ; Male ; Medical sciences ; Membrane Glycoproteins - metabolism ; Membrane Transport Proteins ; Morpholines - chemistry ; Nerve Tissue Proteins ; Neuropharmacology ; Norepinephrine - metabolism ; Norepinephrine Plasma Membrane Transport Proteins ; Pharmacology. Drug treatments ; Piperidines - chemical synthesis ; Piperidines - chemistry ; Piperidines - pharmacology ; Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease) ; Psychology. Psychoanalysis. Psychiatry ; Psychopharmacology ; Radioligand Assay ; Rats ; Rats, Wistar ; Receptor, Serotonin, 5-HT1A - metabolism ; Receptor, Serotonin, 5-HT2A - metabolism ; Serotonin - metabolism ; Serotonin Plasma Membrane Transport Proteins ; Serotonin Uptake Inhibitors - chemical synthesis ; Serotonin Uptake Inhibitors - chemistry ; Serotonin Uptake Inhibitors - pharmacology ; Stereoisomerism ; Structure-Activity Relationship ; Symporters - metabolism</subject><ispartof>Journal of medicinal chemistry, 2003-12, Vol.46 (25), p.5512-5532</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-c4e42ebc55fbda8b7e5da253518bffe903b80c1a656743d36d64d50d0c0c82313</citedby><cites>FETCH-LOGICAL-a379t-c4e42ebc55fbda8b7e5da253518bffe903b80c1a656743d36d64d50d0c0c82313</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm0309349$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm0309349$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15331383$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14640559$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Orjales, Aurelio</creatorcontrib><creatorcontrib>Mosquera, Ramón</creatorcontrib><creatorcontrib>Toledo, Antonio</creatorcontrib><creatorcontrib>Pumar, M. Carmen</creatorcontrib><creatorcontrib>García, Neftalí</creatorcontrib><creatorcontrib>Cortizo, Lourdes</creatorcontrib><creatorcontrib>Labeaga, Luis</creatorcontrib><creatorcontrib>Innerárity, Ana</creatorcontrib><title>Syntheses and Binding Studies of New [(Aryl)(aryloxy)methyl]piperidine Derivatives and Related Compounds as Potential Antidepressant Drugs with High Affinity for Serotonin (5-HT) and Norepinephrine (NE) Transporters</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>In a wide search program toward new, efficient, and fast-acting antidepressant drugs, we have prepared series of new compounds having an (aryl)(aryloxy)methyl moiety linked directly or through a methylene chain to different substituted and unsubstituted cycles (isoquinoline, piperazine, piperidine, tetrahydropyran, or cyclopentane). These compounds have been evaluated for their affinities for serotonin (5-HT) transporter (SERT) and 5-HT1A and 5-HT2A receptors. Racemic mixtures of 4-[(aryl)(aryloxy)methyl]piperidine derivatives showed much higher affinity values for SERT than fluoxetine and resulted in lack of affinity for 5-HT1A and 5-HT2A receptors. Some of these racemic mixtures were resolved to their enantiomers and tested for binding to norepinephrine (NE) transporter (NET), dopamine (DA) transporter (DAT), and α2 receptor. Several of these enantiomers [( − )-15b, ( − )-15j, ( − )-15t, (+)-15u] displayed a dual binding profile with affinities for SERT and NET with K i < 25 nM and a NET/SERT ratio <10. Compound ( − )-15j (coded as F-98214-TA for development studies) showed a dual binding profile with very high affinity values for SERT and NET (K i = 1.9 and 13.5 nM, respectively), and further pharmacological characterization is in progress for its evaluation as a antidepressant.</description><subject>Adrenergic Uptake Inhibitors - chemical synthesis</subject><subject>Adrenergic Uptake Inhibitors - chemistry</subject><subject>Adrenergic Uptake Inhibitors - pharmacology</subject><subject>Animals</subject><subject>Antidepressive Agents - chemical synthesis</subject><subject>Antidepressive Agents - chemistry</subject><subject>Antidepressive Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Brain - metabolism</subject><subject>Carrier Proteins - metabolism</subject><subject>Fluoxetine - analogs & derivatives</subject><subject>Fluoxetine - chemistry</subject><subject>In Vitro Techniques</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Membrane Glycoproteins - metabolism</subject><subject>Membrane Transport Proteins</subject><subject>Morpholines - chemistry</subject><subject>Nerve Tissue Proteins</subject><subject>Neuropharmacology</subject><subject>Norepinephrine - metabolism</subject><subject>Norepinephrine Plasma Membrane Transport Proteins</subject><subject>Pharmacology. Drug treatments</subject><subject>Piperidines - chemical synthesis</subject><subject>Piperidines - chemistry</subject><subject>Piperidines - pharmacology</subject><subject>Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease)</subject><subject>Psychology. Psychoanalysis. Psychiatry</subject><subject>Psychopharmacology</subject><subject>Radioligand Assay</subject><subject>Rats</subject><subject>Rats, Wistar</subject><subject>Receptor, Serotonin, 5-HT1A - metabolism</subject><subject>Receptor, Serotonin, 5-HT2A - metabolism</subject><subject>Serotonin - metabolism</subject><subject>Serotonin Plasma Membrane Transport Proteins</subject><subject>Serotonin Uptake Inhibitors - chemical synthesis</subject><subject>Serotonin Uptake Inhibitors - chemistry</subject><subject>Serotonin Uptake Inhibitors - pharmacology</subject><subject>Stereoisomerism</subject><subject>Structure-Activity Relationship</subject><subject>Symporters - metabolism</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2003</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkV1v0zAUhiMEYmNwwR9AvgG1FwE7jvNxWbqNIpUyaJEQCFlOfNK6S-xgO9v6S_k7eLRab7jxsY4fv-fjjaKXBL8lOCHvth2muKRp-Sg6JSzBcVrg9HF0inGSxEmW0JPomXNbjDElCX0anZA0SzFj5Wn0Z7nTfgMOHBJaovdKS6XXaOkHqULONGgBt-jnaGJ37XgkwmnuduMO_GbX_upVD1aFD4DOw-VGeHVzEPoKrfAg0dR0vRm0DFmHrowH7ZVo0SQECb0F54T26NwOa4duld-gmVpv0KRplFZ-hxpj0RKs8UYrjUYsnq3G__QXxkIfCvcbe19-tLgYo5UV2vXGerDuefSkEa2DF4d4Fn27vFhNZ_H884eP08k8FjQvfVynkCZQ1Yw1lRRFlQOTImGUkaJqGigxrQpcE5GxLE-ppJnMUsmwxDWui4QSeha92ev21vwewHneKVdD2woNZnA8JyktaZ4HcLwHa2ucs9Dw3qouLJQTzO9d5A8uBvbVQXSoOpBH8mBbAF4fAOFq0TZh8Fq5I8doaK2ggYv3nHIe7h7ehb3mWU5zxldXS17-uPyy-PR9zulRV9SOb81gddjdfxr8C3i7w1U</recordid><startdate>20031204</startdate><enddate>20031204</enddate><creator>Orjales, Aurelio</creator><creator>Mosquera, Ramón</creator><creator>Toledo, Antonio</creator><creator>Pumar, M. Carmen</creator><creator>García, Neftalí</creator><creator>Cortizo, Lourdes</creator><creator>Labeaga, Luis</creator><creator>Innerárity, Ana</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>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20031204</creationdate><title>Syntheses and Binding Studies of New [(Aryl)(aryloxy)methyl]piperidine Derivatives and Related Compounds as Potential Antidepressant Drugs with High Affinity for Serotonin (5-HT) and Norepinephrine (NE) Transporters</title><author>Orjales, Aurelio ; Mosquera, Ramón ; Toledo, Antonio ; Pumar, M. Carmen ; García, Neftalí ; Cortizo, Lourdes ; Labeaga, Luis ; Innerárity, Ana</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-c4e42ebc55fbda8b7e5da253518bffe903b80c1a656743d36d64d50d0c0c82313</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Adrenergic Uptake Inhibitors - chemical synthesis</topic><topic>Adrenergic Uptake Inhibitors - chemistry</topic><topic>Adrenergic Uptake Inhibitors - pharmacology</topic><topic>Animals</topic><topic>Antidepressive Agents - chemical synthesis</topic><topic>Antidepressive Agents - chemistry</topic><topic>Antidepressive Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Brain - metabolism</topic><topic>Carrier Proteins - metabolism</topic><topic>Fluoxetine - analogs & derivatives</topic><topic>Fluoxetine - chemistry</topic><topic>In Vitro Techniques</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Membrane Glycoproteins - metabolism</topic><topic>Membrane Transport Proteins</topic><topic>Morpholines - chemistry</topic><topic>Nerve Tissue Proteins</topic><topic>Neuropharmacology</topic><topic>Norepinephrine - metabolism</topic><topic>Norepinephrine Plasma Membrane Transport Proteins</topic><topic>Pharmacology. Drug treatments</topic><topic>Piperidines - chemical synthesis</topic><topic>Piperidines - chemistry</topic><topic>Piperidines - pharmacology</topic><topic>Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease)</topic><topic>Psychology. Psychoanalysis. Psychiatry</topic><topic>Psychopharmacology</topic><topic>Radioligand Assay</topic><topic>Rats</topic><topic>Rats, Wistar</topic><topic>Receptor, Serotonin, 5-HT1A - metabolism</topic><topic>Receptor, Serotonin, 5-HT2A - metabolism</topic><topic>Serotonin - metabolism</topic><topic>Serotonin Plasma Membrane Transport Proteins</topic><topic>Serotonin Uptake Inhibitors - chemical synthesis</topic><topic>Serotonin Uptake Inhibitors - chemistry</topic><topic>Serotonin Uptake Inhibitors - pharmacology</topic><topic>Stereoisomerism</topic><topic>Structure-Activity Relationship</topic><topic>Symporters - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Orjales, Aurelio</creatorcontrib><creatorcontrib>Mosquera, Ramón</creatorcontrib><creatorcontrib>Toledo, Antonio</creatorcontrib><creatorcontrib>Pumar, M. Carmen</creatorcontrib><creatorcontrib>García, Neftalí</creatorcontrib><creatorcontrib>Cortizo, Lourdes</creatorcontrib><creatorcontrib>Labeaga, Luis</creatorcontrib><creatorcontrib>Innerárity, Ana</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>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Orjales, Aurelio</au><au>Mosquera, Ramón</au><au>Toledo, Antonio</au><au>Pumar, M. Carmen</au><au>García, Neftalí</au><au>Cortizo, Lourdes</au><au>Labeaga, Luis</au><au>Innerárity, Ana</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Syntheses and Binding Studies of New [(Aryl)(aryloxy)methyl]piperidine Derivatives and Related Compounds as Potential Antidepressant Drugs with High Affinity for Serotonin (5-HT) and Norepinephrine (NE) Transporters</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2003-12-04</date><risdate>2003</risdate><volume>46</volume><issue>25</issue><spage>5512</spage><epage>5532</epage><pages>5512-5532</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>In a wide search program toward new, efficient, and fast-acting antidepressant drugs, we have prepared series of new compounds having an (aryl)(aryloxy)methyl moiety linked directly or through a methylene chain to different substituted and unsubstituted cycles (isoquinoline, piperazine, piperidine, tetrahydropyran, or cyclopentane). These compounds have been evaluated for their affinities for serotonin (5-HT) transporter (SERT) and 5-HT1A and 5-HT2A receptors. Racemic mixtures of 4-[(aryl)(aryloxy)methyl]piperidine derivatives showed much higher affinity values for SERT than fluoxetine and resulted in lack of affinity for 5-HT1A and 5-HT2A receptors. Some of these racemic mixtures were resolved to their enantiomers and tested for binding to norepinephrine (NE) transporter (NET), dopamine (DA) transporter (DAT), and α2 receptor. Several of these enantiomers [( − )-15b, ( − )-15j, ( − )-15t, (+)-15u] displayed a dual binding profile with affinities for SERT and NET with K i < 25 nM and a NET/SERT ratio <10. Compound ( − )-15j (coded as F-98214-TA for development studies) showed a dual binding profile with very high affinity values for SERT and NET (K i = 1.9 and 13.5 nM, respectively), and further pharmacological characterization is in progress for its evaluation as a antidepressant.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>14640559</pmid><doi>10.1021/jm0309349</doi><tpages>21</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 2003-12, Vol.46 (25), p.5512-5532 |
| issn | 0022-2623 1520-4804 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Adrenergic Uptake Inhibitors - chemical synthesis Adrenergic Uptake Inhibitors - chemistry Adrenergic Uptake Inhibitors - pharmacology Animals Antidepressive Agents - chemical synthesis Antidepressive Agents - chemistry Antidepressive Agents - pharmacology Biological and medical sciences Brain - metabolism Carrier Proteins - metabolism Fluoxetine - analogs & derivatives Fluoxetine - chemistry In Vitro Techniques Male Medical sciences Membrane Glycoproteins - metabolism Membrane Transport Proteins Morpholines - chemistry Nerve Tissue Proteins Neuropharmacology Norepinephrine - metabolism Norepinephrine Plasma Membrane Transport Proteins Pharmacology. Drug treatments Piperidines - chemical synthesis Piperidines - chemistry Piperidines - pharmacology Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease) Psychology. Psychoanalysis. Psychiatry Psychopharmacology Radioligand Assay Rats Rats, Wistar Receptor, Serotonin, 5-HT1A - metabolism Receptor, Serotonin, 5-HT2A - metabolism Serotonin - metabolism Serotonin Plasma Membrane Transport Proteins Serotonin Uptake Inhibitors - chemical synthesis Serotonin Uptake Inhibitors - chemistry Serotonin Uptake Inhibitors - pharmacology Stereoisomerism Structure-Activity Relationship Symporters - metabolism |
| title | Syntheses and Binding Studies of New [(Aryl)(aryloxy)methyl]piperidine Derivatives and Related Compounds as Potential Antidepressant Drugs with High Affinity for Serotonin (5-HT) and Norepinephrine (NE) Transporters |
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