Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors
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2012
Authors
Šukalović, Vladimir
Ignjatović, Đurđica S.

Tovilović, Gordana

Andrić, Deana

Shakib, Kaveh

Kostić Rajačić, Slađana

Šoškić, Vukić

Article (Published version)

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It is suggested that the ratio of dopamine D-2 to 5-hydroxytryptamine 5-HT1A activity is an important parameter that determines the efficiency of antipsychotic drugs. Here we present the synthesis of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas and their structure-activity relationship studies on dopamine D-2 and 5-hydrohytryptamine 5-HT1A receptors. It was shown that ligand selectivity and affinity strongly depends on their topology and the presence of a pyridyl group in the head of molecules. Molecular modeling studies using homology modeling and docking simulation revealed a rational explanation for the ligand behavior. The observed binding modes and receptor-ligand interactions provided us with a clue for optimizing the optimal selectivity towards 5-HT1A receptors.
Keywords:
Dopamine / 5-Hydroxytryptamine / Receptor / Arylpiperazine / Molecular dockingSource:
Bioorganic and Medicinal Chemistry Letters, 2012, 22, 12, 3967-3972Publisher:
- Oxford : Pergamon-Elsevier Science Ltd
Funding / projects:
DOI: 10.1016/j.bmcl.2012.04.098
ISSN: 0960-894X
PubMed: 22607670
WoS: 000304484600023
Scopus: 2-s2.0-84861576055
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IHTMTY - JOUR AU - Šukalović, Vladimir AU - Ignjatović, Đurđica S. AU - Tovilović, Gordana AU - Andrić, Deana AU - Shakib, Kaveh AU - Kostić Rajačić, Slađana AU - Šoškić, Vukić PY - 2012 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/974 AB - It is suggested that the ratio of dopamine D-2 to 5-hydroxytryptamine 5-HT1A activity is an important parameter that determines the efficiency of antipsychotic drugs. Here we present the synthesis of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas and their structure-activity relationship studies on dopamine D-2 and 5-hydrohytryptamine 5-HT1A receptors. It was shown that ligand selectivity and affinity strongly depends on their topology and the presence of a pyridyl group in the head of molecules. Molecular modeling studies using homology modeling and docking simulation revealed a rational explanation for the ligand behavior. The observed binding modes and receptor-ligand interactions provided us with a clue for optimizing the optimal selectivity towards 5-HT1A receptors. PB - Oxford : Pergamon-Elsevier Science Ltd T2 - Bioorganic and Medicinal Chemistry Letters T1 - Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors VL - 22 IS - 12 SP - 3967 EP - 3972 DO - 10.1016/j.bmcl.2012.04.098 ER -
@article{ author = "Šukalović, Vladimir and Ignjatović, Đurđica S. and Tovilović, Gordana and Andrić, Deana and Shakib, Kaveh and Kostić Rajačić, Slađana and Šoškić, Vukić", year = "2012", abstract = "It is suggested that the ratio of dopamine D-2 to 5-hydroxytryptamine 5-HT1A activity is an important parameter that determines the efficiency of antipsychotic drugs. Here we present the synthesis of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas and their structure-activity relationship studies on dopamine D-2 and 5-hydrohytryptamine 5-HT1A receptors. It was shown that ligand selectivity and affinity strongly depends on their topology and the presence of a pyridyl group in the head of molecules. Molecular modeling studies using homology modeling and docking simulation revealed a rational explanation for the ligand behavior. The observed binding modes and receptor-ligand interactions provided us with a clue for optimizing the optimal selectivity towards 5-HT1A receptors.", publisher = "Oxford : Pergamon-Elsevier Science Ltd", journal = "Bioorganic and Medicinal Chemistry Letters", title = "Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors", volume = "22", number = "12", pages = "3967-3972", doi = "10.1016/j.bmcl.2012.04.098" }
Šukalović, V., Ignjatović, Đ. S., Tovilović, G., Andrić, D., Shakib, K., Kostić Rajačić, S.,& Šoškić, V.. (2012). Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors. in Bioorganic and Medicinal Chemistry Letters Oxford : Pergamon-Elsevier Science Ltd., 22(12), 3967-3972. https://doi.org/10.1016/j.bmcl.2012.04.098
Šukalović V, Ignjatović ĐS, Tovilović G, Andrić D, Shakib K, Kostić Rajačić S, Šoškić V. Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors. in Bioorganic and Medicinal Chemistry Letters. 2012;22(12):3967-3972. doi:10.1016/j.bmcl.2012.04.098 .
Šukalović, Vladimir, Ignjatović, Đurđica S., Tovilović, Gordana, Andrić, Deana, Shakib, Kaveh, Kostić Rajačić, Slađana, Šoškić, Vukić, "Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors" in Bioorganic and Medicinal Chemistry Letters, 22, no. 12 (2012):3967-3972, https://doi.org/10.1016/j.bmcl.2012.04.098 . .