TY  - JOUR
AU  - Šukalović, Vladimir
AU  - Bogdan, Anca Elena
AU  - Tovilović-Kovačević, Gordana
AU  - Ignjatović, Đurđica
AU  - Andrić, Deana
AU  - Kostić-Rajačić, Slađana
AU  - Šoškić, Vukić
PY  - 2013
UR  - http://radar.ibiss.bg.ac.rs/handle/123456789/6804
AB  - The ratio of affinities toward the dopamine D-2 and the 5-hydroxytryptamine 5-HT1A receptors is one of the important parameters that determine the efficiency of antipsychotic drugs. Here, we present the synthesis of ortho-, meta-, and para-N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides and their structure-activity relationship studies on dopamine D-2 and 5-hydroxytryptamine 5-HT1A receptors. It was shown that the biological activity of the described ligands strongly depends on their topology as well as on the nature of the heteroaryl group in the head of the molecules. Docking simulations together with conformational analysis revealed a rational explanation for the ligands' behavior. The molecular model of receptor-ligand interactions described herein provided us with a tool for the rational design of new compounds with a favorable D-2/5-HT1A profile.
PB  - Weinheim: Wiley-V C H Verlag Gmbh
T2  - Archiv der Pharmazie
T1  - N-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling
IS  - 10
VL  - 346
DO  - 10.1002/ardp.201300189
SP  - 708
EP  - 717
ER  - 

@article{
author = "Šukalović, Vladimir and Bogdan, Anca Elena and Tovilović-Kovačević, Gordana and Ignjatović, Đurđica and Andrić, Deana and Kostić-Rajačić, Slađana and Šoškić, Vukić",
year = "2013",
abstract = "The ratio of affinities toward the dopamine D-2 and the 5-hydroxytryptamine 5-HT1A receptors is one of the important parameters that determine the efficiency of antipsychotic drugs. Here, we present the synthesis of ortho-, meta-, and para-N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides and their structure-activity relationship studies on dopamine D-2 and 5-hydroxytryptamine 5-HT1A receptors. It was shown that the biological activity of the described ligands strongly depends on their topology as well as on the nature of the heteroaryl group in the head of the molecules. Docking simulations together with conformational analysis revealed a rational explanation for the ligands' behavior. The molecular model of receptor-ligand interactions described herein provided us with a tool for the rational design of new compounds with a favorable D-2/5-HT1A profile.",
publisher = "Weinheim: Wiley-V C H Verlag Gmbh",
journal = "Archiv der Pharmazie",
title = "N-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling",
number = "10",
volume = "346",
doi = "10.1002/ardp.201300189",
pages = "708-717"
}

Šukalović, V., Bogdan, A. E., Tovilović-Kovačević, G., Ignjatović, Đ., Andrić, D., Kostić-Rajačić, S.,& Šoškić, V.. (2013). N-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling. in Archiv der Pharmazie
Weinheim: Wiley-V C H Verlag Gmbh., 346(10), 708-717.
https://doi.org/10.1002/ardp.201300189

Šukalović V, Bogdan AE, Tovilović-Kovačević G, Ignjatović Đ, Andrić D, Kostić-Rajačić S, Šoškić V. N-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling. in Archiv der Pharmazie. 2013;346(10):708-717.
doi:10.1002/ardp.201300189 .

Šukalović, Vladimir, Bogdan, Anca Elena, Tovilović-Kovačević, Gordana, Ignjatović, Đurđica, Andrić, Deana, Kostić-Rajačić, Slađana, Šoškić, Vukić, "N-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling" in Archiv der Pharmazie, 346, no. 10 (2013):708-717,
https://doi.org/10.1002/ardp.201300189 . .

TY  - JOUR
AU  - Šukalović, Vladimir
AU  - Ignjatović, Đurđica
AU  - Tovilović-Kovačević, Gordana
AU  - Andrić, Deana
AU  - Shakib, Kaveh
AU  - Kostić-Rajačić, Slađana
AU  - Šoškić, Vukić
PY  - 2012
UR  - http://radar.ibiss.bg.ac.rs/handle/123456789/6836
AB  - It is suggested that the ratio of dopamine D2 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 D2
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) receptor
IS  - 12
VL  - 22
DO  - 10.1016/j.bmcl.2012.04.098
SP  - 3967
EP  - 3972
ER  - 

@article{
author = "Šukalović, Vladimir and Ignjatović, Đurđica and Tovilović-Kovačević, 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 D2 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 D2
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) receptor",
number = "12",
volume = "22",
doi = "10.1016/j.bmcl.2012.04.098",
pages = "3967-3972"
}

Šukalović, V., Ignjatović, Đ., Tovilović-Kovačević, 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) receptor. 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 Đ, Tovilović-Kovačević 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) receptor. in Bioorganic and Medicinal Chemistry Letters. 2012;22(12):3967-3972.
doi:10.1016/j.bmcl.2012.04.098 .

Šukalović, Vladimir, Ignjatović, Đurđica, Tovilović-Kovačević, 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) receptor" in Bioorganic and Medicinal Chemistry Letters, 22, no. 12 (2012):3967-3972,
https://doi.org/10.1016/j.bmcl.2012.04.098 . .

TY  - JOUR
AU  - Ignjatović, Đurđica
AU  - Vojnović Milutinović, Danijela
AU  - Nikolić-Kokić, Aleksandra
AU  - Slavić, Marija
AU  - Andrić, Deana
AU  - Tomić, Mirko
AU  - Kostić-Rajačić, Slađana
PY  - 2012
UR  - http://radar.ibiss.bg.ac.rs/handle/123456789/6835
AB  - A group of sixteen arylpiperazines had been previously synthesized and evaluated for atypical antipsychotic
activity. Here we examined these compounds for their neuroprotective capacity. The affinity and agonist/
antagonist action of the arylpiperazines at dopamine hD2S receptors were determined in vitro on membranes
from stably transfected CHO-hD2S cell line. The assays for cell viability and antioxidative capacity (total
glutathione and total superoxide dismutase activity), amount of nitric oxide and superoxide radicals, as
well as influence on prosurvival pathways (Akt and ERK), were performed on the human neuroblastoma
cell line SH-SY5Y. Cell death was induced by oxidative or nitrosative stress, or by growing cells in the medium
deprived of serum. Only four of the arylpiperazines exhibited notable neuroprotection against cell death
induced by sodium nitroprusside. Two of these arylpiperazines induced elevations of pAkt, while two other
compounds reduced the levels of pErk, whereas these actions are considered to support the cell survival.
The benzimidazole heteroaryl-group, that mimics catechol moiety of the dopamine molecule, might be the
prerequisite structure for the neuroprotective action of these ligands. It is postulated that neuroprotection
was acquired also by elevation of endogenous glutathione or total superoxide dismutase activity.
PB  - Amsterdam, Netherlands: Elsevier
T2  - European Journal of Pharmacology
T1  - The mechanisms responsible for neuroprotective capacity of arylpiperazine dopaminergic ligands against cell death induced by sodium nitroprusside
IS  - 1-3
VL  - 683
DO  - 10.1016/j.ejphar.2012.03.011
SP  - 93
EP  - 100
ER  - 

@article{
author = "Ignjatović, Đurđica and Vojnović Milutinović, Danijela and Nikolić-Kokić, Aleksandra and Slavić, Marija and Andrić, Deana and Tomić, Mirko and Kostić-Rajačić, Slađana",
year = "2012",
abstract = "A group of sixteen arylpiperazines had been previously synthesized and evaluated for atypical antipsychotic
activity. Here we examined these compounds for their neuroprotective capacity. The affinity and agonist/
antagonist action of the arylpiperazines at dopamine hD2S receptors were determined in vitro on membranes
from stably transfected CHO-hD2S cell line. The assays for cell viability and antioxidative capacity (total
glutathione and total superoxide dismutase activity), amount of nitric oxide and superoxide radicals, as
well as influence on prosurvival pathways (Akt and ERK), were performed on the human neuroblastoma
cell line SH-SY5Y. Cell death was induced by oxidative or nitrosative stress, or by growing cells in the medium
deprived of serum. Only four of the arylpiperazines exhibited notable neuroprotection against cell death
induced by sodium nitroprusside. Two of these arylpiperazines induced elevations of pAkt, while two other
compounds reduced the levels of pErk, whereas these actions are considered to support the cell survival.
The benzimidazole heteroaryl-group, that mimics catechol moiety of the dopamine molecule, might be the
prerequisite structure for the neuroprotective action of these ligands. It is postulated that neuroprotection
was acquired also by elevation of endogenous glutathione or total superoxide dismutase activity.",
publisher = "Amsterdam, Netherlands: Elsevier",
journal = "European Journal of Pharmacology",
title = "The mechanisms responsible for neuroprotective capacity of arylpiperazine dopaminergic ligands against cell death induced by sodium nitroprusside",
number = "1-3",
volume = "683",
doi = "10.1016/j.ejphar.2012.03.011",
pages = "93-100"
}

Ignjatović, Đ., Vojnović Milutinović, D., Nikolić-Kokić, A., Slavić, M., Andrić, D., Tomić, M.,& Kostić-Rajačić, S.. (2012). The mechanisms responsible for neuroprotective capacity of arylpiperazine dopaminergic ligands against cell death induced by sodium nitroprusside. in European Journal of Pharmacology
Amsterdam, Netherlands: Elsevier., 683(1-3), 93-100.
https://doi.org/10.1016/j.ejphar.2012.03.011

Ignjatović Đ, Vojnović Milutinović D, Nikolić-Kokić A, Slavić M, Andrić D, Tomić M, Kostić-Rajačić S. The mechanisms responsible for neuroprotective capacity of arylpiperazine dopaminergic ligands against cell death induced by sodium nitroprusside. in European Journal of Pharmacology. 2012;683(1-3):93-100.
doi:10.1016/j.ejphar.2012.03.011 .

Ignjatović, Đurđica, Vojnović Milutinović, Danijela, Nikolić-Kokić, Aleksandra, Slavić, Marija, Andrić, Deana, Tomić, Mirko, Kostić-Rajačić, Slađana, "The mechanisms responsible for neuroprotective capacity of arylpiperazine dopaminergic ligands against cell death induced by sodium nitroprusside" in European Journal of Pharmacology, 683, no. 1-3 (2012):93-100,
https://doi.org/10.1016/j.ejphar.2012.03.011 . .