Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands
Само за регистроване кориснике
2016
Аутори
Penjišević, JelenaŠukalović, Vladimir
Andrić, Deana
Roglić, Goran
Šoškić, Vukić
Kostić Rajačić, Slađana
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Sixteen new 1-(2-methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines were synthesized to be used as probes for mapping the dopamine D-2 receptor (D(2)DAR) arylpiperazine binding site. All compounds were evaluated for their affinity toward D(2)DAR in an in vitro competitive displacement assay. The most active one was 1-(2-methoxyphenyl)-4-{[1-(3-nitrophenethyl)piperidin-4-yl]methyl}piperazine (25) with an affinity of K-i = 54 nM. Docking analysis was conducted on all herein described compounds, whereas molecular dynamic simulation was performed on ligand 25 to establish its mode of interaction with D(2)DAR. Two possible docking orientations are proposed; the one with a salt bridge between the piperidine moiety and Asp114 of D(2)DAR is more stable.
Кључне речи:
Docking analysis / Dopamine D-2 receptors / N-ArylpiperazinesИзвор:
Archiv der Pharmazie, 2016, 349, 8, 614-626Издавач:
- Wiley-V C H Verlag Gmbh, Weinheim
Финансирање / пројекти:
DOI: 10.1002/ardp.201600081
ISSN: 0365-6233
PubMed: 27335270
WoS: 000380903600004
Scopus: 2-s2.0-84982803374
Институција/група
IHTMTY - JOUR AU - Penjišević, Jelena AU - Šukalović, Vladimir AU - Andrić, Deana AU - Roglić, Goran AU - Šoškić, Vukić AU - Kostić Rajačić, Slađana PY - 2016 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1880 AB - Sixteen new 1-(2-methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines were synthesized to be used as probes for mapping the dopamine D-2 receptor (D(2)DAR) arylpiperazine binding site. All compounds were evaluated for their affinity toward D(2)DAR in an in vitro competitive displacement assay. The most active one was 1-(2-methoxyphenyl)-4-{[1-(3-nitrophenethyl)piperidin-4-yl]methyl}piperazine (25) with an affinity of K-i = 54 nM. Docking analysis was conducted on all herein described compounds, whereas molecular dynamic simulation was performed on ligand 25 to establish its mode of interaction with D(2)DAR. Two possible docking orientations are proposed; the one with a salt bridge between the piperidine moiety and Asp114 of D(2)DAR is more stable. PB - Wiley-V C H Verlag Gmbh, Weinheim T2 - Archiv der Pharmazie T1 - Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands VL - 349 IS - 8 SP - 614 EP - 626 DO - 10.1002/ardp.201600081 ER -
@article{ author = "Penjišević, Jelena and Šukalović, Vladimir and Andrić, Deana and Roglić, Goran and Šoškić, Vukić and Kostić Rajačić, Slađana", year = "2016", abstract = "Sixteen new 1-(2-methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines were synthesized to be used as probes for mapping the dopamine D-2 receptor (D(2)DAR) arylpiperazine binding site. All compounds were evaluated for their affinity toward D(2)DAR in an in vitro competitive displacement assay. The most active one was 1-(2-methoxyphenyl)-4-{[1-(3-nitrophenethyl)piperidin-4-yl]methyl}piperazine (25) with an affinity of K-i = 54 nM. Docking analysis was conducted on all herein described compounds, whereas molecular dynamic simulation was performed on ligand 25 to establish its mode of interaction with D(2)DAR. Two possible docking orientations are proposed; the one with a salt bridge between the piperidine moiety and Asp114 of D(2)DAR is more stable.", publisher = "Wiley-V C H Verlag Gmbh, Weinheim", journal = "Archiv der Pharmazie", title = "Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands", volume = "349", number = "8", pages = "614-626", doi = "10.1002/ardp.201600081" }
Penjišević, J., Šukalović, V., Andrić, D., Roglić, G., Šoškić, V.,& Kostić Rajačić, S.. (2016). Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands. in Archiv der Pharmazie Wiley-V C H Verlag Gmbh, Weinheim., 349(8), 614-626. https://doi.org/10.1002/ardp.201600081
Penjišević J, Šukalović V, Andrić D, Roglić G, Šoškić V, Kostić Rajačić S. Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands. in Archiv der Pharmazie. 2016;349(8):614-626. doi:10.1002/ardp.201600081 .
Penjišević, Jelena, Šukalović, Vladimir, Andrić, Deana, Roglić, Goran, Šoškić, Vukić, Kostić Rajačić, Slađana, "Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands" in Archiv der Pharmazie, 349, no. 8 (2016):614-626, https://doi.org/10.1002/ardp.201600081 . .