Design, synthesis, and evaluation of functionalized 5-(4-arylpiperazin-1-yl)-N-arylpentanamides as selective dopamine D3 receptor ligands
Substance use disorder remains a major, unmet medical need. Cocaine is one of the most commonly abused recreational drugs and in 2018, there were over 5.5 million cocaine users. There are no approved therapies for the treatment of cocaine use disorder, but the D 3 dopamine receptor has been identifi...
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Published in | Medicinal chemistry research Vol. 31; no. 1; pp. 132 - 145 |
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Main Authors | , , , , , |
Format | Journal Article |
Language | English |
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Abstract | Substance use disorder remains a major, unmet medical need. Cocaine is one of the most commonly abused recreational drugs and in 2018, there were over 5.5 million cocaine users. There are no approved therapies for the treatment of cocaine use disorder, but the D
3
dopamine receptor has been identified as a potential therapeutic target. Our initial lead compound (
6
) is a potent D
3
ligand with a high level of selectivity for D
3
over D
2
, but its solubility is low. We have identified a new series of functionalized 5-(4-arylpiperazin-1-yl)-N-arylpentanamides (
7
) that are potent D
3
binders that have moderate to high selectivity for D
3
over D
2
. Exemplary members of this series were also significantly more soluble than our initial lead compound (
6
). |
---|---|
AbstractList | Substance use disorder remains a major, unmet medical need. Cocaine is one of the most commonly abused recreational drugs and in 2018, there were over 5.5 million cocaine users. There are no approved therapies for the treatment of cocaine use disorder, but the D
3
dopamine receptor has been identified as a potential therapeutic target. Our initial lead compound (
6
) is a potent D
3
ligand with a high level of selectivity for D
3
over D
2
, but its solubility is low. We have identified a new series of functionalized 5-(4-arylpiperazin-1-yl)-N-arylpentanamides (
7
) that are potent D
3
binders that have moderate to high selectivity for D
3
over D
2
. Exemplary members of this series were also significantly more soluble than our initial lead compound (
6
). Substance use disorder remains a major, unmet medical need. Cocaine is one of the most commonly abused recreational drugs and in 2018, there were over 5.5 million cocaine users. There are no approved therapies for the treatment of cocaine use disorder, but the D3 dopamine receptor has been identified as a potential therapeutic target. Our initial lead compound (6) is a potent D3 ligand with a high level of selectivity for D3 over D2, but its solubility is low. We have identified a new series of functionalized 5-(4-arylpiperazin-1-yl)-N-arylpentanamides (7) that are potent D3 binders that have moderate to high selectivity for D3 over D2. Exemplary members of this series were also significantly more soluble than our initial lead compound (6). |
Author | Taylor, Michelle Griffin, Suzy A. Gordon, John C. Chen, Peng-Jen Blass, Benjamin E. Luedtke, Robert R. |
Author_xml | – sequence: 1 givenname: Benjamin E. orcidid: 0000-0003-2449-4503 surname: Blass fullname: Blass, Benjamin E. email: Benjamin.Blass@Temple.edu organization: Department of Pharmaceutical Sciences, Temple University School of Pharmacy – sequence: 2 givenname: Peng-Jen surname: Chen fullname: Chen, Peng-Jen organization: Department of Pharmaceutical Sciences, Temple University School of Pharmacy – sequence: 3 givenname: Michelle surname: Taylor fullname: Taylor, Michelle organization: Department of Pharmacology and Neuroscience, Center, University of North Texas Health Science – sequence: 4 givenname: Suzy A. surname: Griffin fullname: Griffin, Suzy A. organization: Department of Pharmacology and Neuroscience, Center, University of North Texas Health Science – sequence: 5 givenname: John C. surname: Gordon fullname: Gordon, John C. organization: Department of Pharmaceutical Sciences, Temple University School of Pharmacy – sequence: 6 givenname: Robert R. surname: Luedtke fullname: Luedtke, Robert R. organization: Department of Pharmacology and Neuroscience, Center, University of North Texas Health Science |
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Cites_doi | 10.3389/fncir.2013.00152 10.33588/rn.6807.2018119 10.1016/j.drugalcdep.2010.07.022 10.2146/ajhp160542 10.1021/jm501512b 10.1016/s0376-8716(98)00050-7 10.1111/j.1749-6632.1999.tb09286.x 10.1038/npp.2013.261 10.1016/j.pbb.2006.04.011 10.1016/j.bcp.2012.06.023 10.1016/j.neuropharm.2015.09.028 10.1016/s0028-3908(96)00100-1 10.2174/1874473711205040006 10.1016/j.bmcl.2019.07.020 10.1001/jamapsychiatry.2013.872 10.1016/j.tins.2013.03.003 10.1016/s0169-328x(97)00025-9 10.1001/jamapsychiatry.2013.2295 10.1038/npp.2011.170 10.1021/acschemneuro.8b00142 10.1523/JNEUROSCI.16-19-06100.1996 10.1016/j.pnpbp.2013.08.012 10.1124/dmd.108.023853 10.2174/1874473711003010049 10.1196/annals.1300.023 10.1124/jpet.107.134536 |
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Keywords | Substance use disorder Cocaine Dopamine D dopamine receptor |
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Snippet | Substance use disorder remains a major, unmet medical need. Cocaine is one of the most commonly abused recreational drugs and in 2018, there were over 5.5... |
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SubjectTerms | Biochemistry Biomedical and Life Sciences Biomedicine Bioorganic Chemistry Cocaine Dopamine Dopamine D2 receptors Dopamine D3 receptors Drug abuse Drug development Inorganic Chemistry Lead compounds Ligands Medicinal Chemistry Original Research Pharmacology/Toxicology Receptors Selectivity Therapeutic targets |
Title | Design, synthesis, and evaluation of functionalized 5-(4-arylpiperazin-1-yl)-N-arylpentanamides as selective dopamine D3 receptor ligands |
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