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Synthesis and pharmacological evaluation of 4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalenyl amines as triple reuptake inhibitors
The present work describes a series of novel chiral amines that potently inhibit the in vitro reuptake of serotonin, norepinephrine and dopamine (triple reuptake inhibitors) and were active in vivo in a mouse model predictive of antidepressant like activity. The detailed synthesis and in vitro activ...
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| Published in: | Bioorganic & medicinal chemistry 2011-01, Vol.19 (1), p.663-676 |
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| Main Authors: | , , , , , , , , , , , , , , |
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| cites | cdi_FETCH-LOGICAL-c504t-2bacfa51b493643eeab6a0a1f2e80041c83fcfa3c9ef9bf4df16922af5e8877f3 |
| container_end_page | 676 |
| container_issue | 1 |
| container_start_page | 663 |
| container_title | Bioorganic & medicinal chemistry |
| container_volume | 19 |
| creator | Shao, Liming Wang, Fengjiang Malcolm, Scott C. Ma, Jianguo Hewitt, Michael C. Campbell, Una C. Bush, Larry R. Spicer, Nancy A. Engel, Sharon R. Saraswat, Lakshmi D. Hardy, Larry W. Koch, Patrick Schreiber, Rudy Spear, Kerry L. Varney, Mark A. |
| description | The present work describes a series of novel chiral amines that potently inhibit the in vitro reuptake of serotonin, norepinephrine and dopamine (triple reuptake inhibitors) and were active in vivo in a mouse model predictive of antidepressant like activity. The detailed synthesis and in vitro activity and ADME profile of compounds is described, which represent a previously undisclosed triple reuptake inhibitor chemotype. |
| doi_str_mv | 10.1016/j.bmc.2010.10.034 |
| format | article |
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Drug treatments ; Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer ; Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease) ; Psychology. Psychoanalysis. Psychiatry ; Psychopharmacology ; serotonin ; Serotonin - metabolism ; Triple uptake inhibitor (TRI)</subject><ispartof>Bioorganic & medicinal chemistry, 2011-01, Vol.19 (1), p.663-676</ispartof><rights>2010 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2010 Elsevier Ltd. 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Psychiatry</subject><subject>Psychopharmacology</subject><subject>serotonin</subject><subject>Serotonin - metabolism</subject><subject>Triple uptake inhibitor (TRI)</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqF0c1u1DAQB_AIgehSeAAukAsCpM3ir2RjcUIVX1IFh9KzNXHGjRcnTm2n0j4Fr4yXXeAGJ8vWb2Zs_4viKSUbSmjzZrfpRr1h5Nd-Q7i4V6yoaETFuaT3ixWRTVuRVjZnxaMYd4QQJiR9WJwxSiRnW74qflztpzRgtLGEqS_nAcII2jt_YzW4Eu_ALZCsn0pvSlG94mtR9VYPzgc_Dzjt3evqSzViGvauomu2PoCEKcCw74OfYB7SAO4ASxjthHlOLFOws8My4DIn-I6lnQbb2eRDfFw8MOAiPjmt58X1h_ffLj5Vl18_fr54d1npmohUsQ60gZp2QvJGcEToGiBADcOWEEF1y00GXEs0sjOiN7SRjIGpsW23W8PPi5fHvnPwtwvGpEYbNToHE_olqrblhHLW0v9Lxngtt6LOkh6lDj7GgEbNwY4Q9ooSdQhM7VQOTB0COxzlwHLNs1P3pRux_1PxO6EMXpwAxJyICTBpG_86vmUNb1l2z4_OgFdwE7K5vsqTapKn5afLLN4eBeZ_vbMYVNQWJ429DaiT6r39x0V_Au0hvgw</recordid><startdate>20110101</startdate><enddate>20110101</enddate><creator>Shao, Liming</creator><creator>Wang, Fengjiang</creator><creator>Malcolm, Scott C.</creator><creator>Ma, Jianguo</creator><creator>Hewitt, Michael C.</creator><creator>Campbell, Una C.</creator><creator>Bush, Larry R.</creator><creator>Spicer, Nancy A.</creator><creator>Engel, Sharon R.</creator><creator>Saraswat, Lakshmi D.</creator><creator>Hardy, Larry W.</creator><creator>Koch, Patrick</creator><creator>Schreiber, Rudy</creator><creator>Spear, Kerry L.</creator><creator>Varney, Mark A.</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>20110101</creationdate><title>Synthesis and pharmacological evaluation of 4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalenyl amines as triple reuptake inhibitors</title><author>Shao, Liming ; Wang, Fengjiang ; Malcolm, Scott C. ; Ma, Jianguo ; Hewitt, Michael C. ; Campbell, Una C. ; Bush, Larry R. ; Spicer, Nancy A. ; Engel, Sharon R. ; Saraswat, Lakshmi D. ; Hardy, Larry W. ; Koch, Patrick ; Schreiber, Rudy ; Spear, Kerry L. ; Varney, Mark A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c504t-2bacfa51b493643eeab6a0a1f2e80041c83fcfa3c9ef9bf4df16922af5e8877f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>animal models</topic><topic>Animals</topic><topic>Antidepressant</topic><topic>antidepressants</topic><topic>Antidepressive Agents - chemical synthesis</topic><topic>Antidepressive Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>chemistry</topic><topic>chemotypes</topic><topic>Depression</topic><topic>Disease Models, Animal</topic><topic>dopamine</topic><topic>Dopamine - metabolism</topic><topic>Drug Evaluation, Preclinical</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Monoamine transporter</topic><topic>Naphthalenes - chemical synthesis</topic><topic>Naphthalenes - pharmacology</topic><topic>Neuropharmacology</topic><topic>Neurotransmitter Uptake Inhibitors - chemical synthesis</topic><topic>Neurotransmitter Uptake Inhibitors - pharmacology</topic><topic>norepinephrine</topic><topic>Norepinephrine - metabolism</topic><topic>Pharmacology. 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| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2011-01, Vol.19 (1), p.663-676 |
| issn | 0968-0896 1464-3391 |
| language | eng |
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| source | ScienceDirect Freedom Collection |
| subjects | animal models Animals Antidepressant antidepressants Antidepressive Agents - chemical synthesis Antidepressive Agents - pharmacology Biological and medical sciences chemistry chemotypes Depression Disease Models, Animal dopamine Dopamine - metabolism Drug Evaluation, Preclinical Medical sciences Mice Monoamine transporter Naphthalenes - chemical synthesis Naphthalenes - pharmacology Neuropharmacology Neurotransmitter Uptake Inhibitors - chemical synthesis Neurotransmitter Uptake Inhibitors - pharmacology norepinephrine Norepinephrine - metabolism Pharmacology. Drug treatments Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease) Psychology. Psychoanalysis. Psychiatry Psychopharmacology serotonin Serotonin - metabolism Triple uptake inhibitor (TRI) |
| title | Synthesis and pharmacological evaluation of 4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalenyl amines as triple reuptake inhibitors |
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