The impact of the halogen bonding on D2 and 5-HT1A/5-HT7 receptor activity of azinesulfonamides of 4-[(2-ethyl)piperidinyl-1-yl]phenylpiperazines with antipsychotic and antidepressant properties
Copyright © 2017 Elsevier Ltd. All rights reserved..
A series of azinesulfonamides of long-chain arylpiperazine derivatives with semi-rigid alkylene spacer was designed, synthesized, and biologically evaluated using in vitro methods for their affinity for dopaminergic D2 and serotoninergic 5-HT1A, 5-HT2A, 5-HT6 and 5-HT7 receptors. Docking to homology models revealed a possible halogen bond formation in complexes of the most potent ligands and the target receptors. The study allowed for the identification of compound 5-({4-(2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethyl)piperidin-1-yl}sulfonyl)quinoline (21), which behaved as D2, 5-HT1A and 5-HT7 receptor antagonist. In preliminary in vivo studies, compound 21 displayed distinct antipsychotic properties in the MK-801-evoked hyperactivity test in mice at a dose of 10mg/kg, and exerted antidepressant-like effect in a forced swim test in mice (MED=0.625mg/kg, i.p.).
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2017 |
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| Erschienen: |
2017 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:25 |
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| Enthalten in: |
Bioorganic & medicinal chemistry - 25(2017), 14 vom: 15. Juli, Seite 3638-3648 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Partyka, Anna [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 02.10.2017 Date Revised 08.12.2017 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.bmc.2017.04.046 |
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| 100 | 1 | |a Partyka, Anna |e verfasserin |4 aut | |
| 245 | 1 | 4 | |a The impact of the halogen bonding on D2 and 5-HT1A/5-HT7 receptor activity of azinesulfonamides of 4-[(2-ethyl)piperidinyl-1-yl]phenylpiperazines with antipsychotic and antidepressant properties |
| 264 | 1 | |c 2017 | |
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| 500 | |a Date Completed 02.10.2017 | ||
| 500 | |a Date Revised 08.12.2017 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright © 2017 Elsevier Ltd. All rights reserved. | ||
| 520 | |a A series of azinesulfonamides of long-chain arylpiperazine derivatives with semi-rigid alkylene spacer was designed, synthesized, and biologically evaluated using in vitro methods for their affinity for dopaminergic D2 and serotoninergic 5-HT1A, 5-HT2A, 5-HT6 and 5-HT7 receptors. Docking to homology models revealed a possible halogen bond formation in complexes of the most potent ligands and the target receptors. The study allowed for the identification of compound 5-({4-(2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethyl)piperidin-1-yl}sulfonyl)quinoline (21), which behaved as D2, 5-HT1A and 5-HT7 receptor antagonist. In preliminary in vivo studies, compound 21 displayed distinct antipsychotic properties in the MK-801-evoked hyperactivity test in mice at a dose of 10mg/kg, and exerted antidepressant-like effect in a forced swim test in mice (MED=0.625mg/kg, i.p.) | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a Azinesulfonamides | |
| 650 | 4 | |a Depression | |
| 650 | 4 | |a Halogen bonding | |
| 650 | 4 | |a Multi-target ligands | |
| 650 | 4 | |a Multimodal dopamine/serotonin ligands | |
| 650 | 4 | |a Schizophrenia | |
| 650 | 4 | |a Semi-rigid long-chain arylpiperazines | |
| 650 | 7 | |a 5-((4-(2-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethyl)piperidin-1-yl)sulfonyl)quinoline |2 NLM | |
| 650 | 7 | |a Antidepressive Agents |2 NLM | |
| 650 | 7 | |a Antipsychotic Agents |2 NLM | |
| 650 | 7 | |a Halogens |2 NLM | |
| 650 | 7 | |a Ligands |2 NLM | |
| 650 | 7 | |a Piperazines |2 NLM | |
| 650 | 7 | |a Receptors, Dopamine D2 |2 NLM | |
| 650 | 7 | |a Receptors, Serotonin |2 NLM | |
| 650 | 7 | |a Sulfonamides |2 NLM | |
| 650 | 7 | |a serotonin 7 receptor |2 NLM | |
| 650 | 7 | |a Receptor, Serotonin, 5-HT1A |2 NLM | |
| 650 | 7 | |a 112692-38-3 |2 NLM | |
| 650 | 7 | |a Dizocilpine Maleate |2 NLM | |
| 650 | 7 | |a 6LR8C1B66Q |2 NLM | |
| 650 | 7 | |a phenylpiperazine |2 NLM | |
| 650 | 7 | |a J9225CBI7D |2 NLM | |
| 700 | 1 | |a Kurczab, Rafał |e verfasserin |4 aut | |
| 700 | 1 | |a Canale, Vittorio |e verfasserin |4 aut | |
| 700 | 1 | |a Satała, Grzegorz |e verfasserin |4 aut | |
| 700 | 1 | |a Marciniec, Krzysztof |e verfasserin |4 aut | |
| 700 | 1 | |a Pasierb, Agnieszka |e verfasserin |4 aut | |
| 700 | 1 | |a Jastrzębska-Więsek, Magdalena |e verfasserin |4 aut | |
| 700 | 1 | |a Pawłowski, Maciej |e verfasserin |4 aut | |
| 700 | 1 | |a Wesołowska, Anna |e verfasserin |4 aut | |
| 700 | 1 | |a Bojarski, Andrzej J |e verfasserin |4 aut | |
| 700 | 1 | |a Zajdel, Paweł |e verfasserin |4 aut | |
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| 856 | 4 | 0 | |u http://dx.doi.org/10.1016/j.bmc.2017.04.046 |3 Volltext |
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