Mixed dopaminergic/serotonergic properties of several 2-substituted 4-[2-(5-benzimidazole)ethyl]-1-arylpiperazines
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1998
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Wiley-VCH Verlag
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A series of substituted 4-[2-(5-benzimidazole)ethyl]-arylpiperazines was synthesized by introducing different substituents into position 2 of benzimidazole ring of 4-[2-(N,N-di-n-propylamino)ethyl]-1,2-diaminobenzenes. They were evaluated for in vitro binding affinity at the D 1 and D 2 dopamine and 5-HT(1A) serotonin receptors using synaptosomal membranes of the bovine caudate nuclei and hippocampi, respectively. Tritiated SCH 23390 (D 1 receptor-selective), spiperone (D 2 receptor selective),and 8-OH-DPAT (5-HT(1A) receptor selective) were employed as the radioligands. Only compound 6 expressed a moderate binding affinity at the dopamine D 1 receptor, while the remaining ligands were inefficient or weak competitors of [ 3 H]SCH 23390. Compound 12 was an absolutely inactive competitor of all three radioligands. Also, compound 7 was an inefficient displacer of [ 3 H]-8-OH-DPAT. Compound 19 with a K(i) value of 3.5 nM was the most potent competitor of [ 3 H]spiperone and compound 13 (K(...i) = 3.3 nM) was the most efficient in displacing [ 3 H]-8-OH-DPAT from the 5-HT(1A) serotonin receptor. Ligands 5, 6, 8-11, and 13-20 expressed mixed dopaminergic/serotonergic activity in nanomolar range of concentrations with varying affinity ratios which strongly depended on the properties of the substituents introduced into position 2 of benzimidazole ring of the parent compounds.
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Archiv der Pharmazie, 1998, 331, 1, 22-26Publisher:
- Wiley-VCH Verlag
Funding / projects:
- Ministry for Science and Technology of Serbia
DOI: 10.1002/(SICI)1521-4184(199801)331:1<22::AID-ARDP22>3.0.CO;2-Q
ISSN: 0365-6233
PubMed: 9507698
Scopus: 2-s2.0-0345698656
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IHTMTY - JOUR AU - Kostić Rajačić, Slađana AU - Šoškić, Vukić AU - Joksimovic, J PY - 1998 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2829 AB - A series of substituted 4-[2-(5-benzimidazole)ethyl]-arylpiperazines was synthesized by introducing different substituents into position 2 of benzimidazole ring of 4-[2-(N,N-di-n-propylamino)ethyl]-1,2-diaminobenzenes. They were evaluated for in vitro binding affinity at the D 1 and D 2 dopamine and 5-HT(1A) serotonin receptors using synaptosomal membranes of the bovine caudate nuclei and hippocampi, respectively. Tritiated SCH 23390 (D 1 receptor-selective), spiperone (D 2 receptor selective),and 8-OH-DPAT (5-HT(1A) receptor selective) were employed as the radioligands. Only compound 6 expressed a moderate binding affinity at the dopamine D 1 receptor, while the remaining ligands were inefficient or weak competitors of [ 3 H]SCH 23390. Compound 12 was an absolutely inactive competitor of all three radioligands. Also, compound 7 was an inefficient displacer of [ 3 H]-8-OH-DPAT. Compound 19 with a K(i) value of 3.5 nM was the most potent competitor of [ 3 H]spiperone and compound 13 (K(i) = 3.3 nM) was the most efficient in displacing [ 3 H]-8-OH-DPAT from the 5-HT(1A) serotonin receptor. Ligands 5, 6, 8-11, and 13-20 expressed mixed dopaminergic/serotonergic activity in nanomolar range of concentrations with varying affinity ratios which strongly depended on the properties of the substituents introduced into position 2 of benzimidazole ring of the parent compounds. PB - Wiley-VCH Verlag T2 - Archiv der Pharmazie T1 - Mixed dopaminergic/serotonergic properties of several 2-substituted 4-[2-(5-benzimidazole)ethyl]-1-arylpiperazines VL - 331 IS - 1 SP - 22 EP - 26 DO - 10.1002/(SICI)1521-4184(199801)331:1<22::AID-ARDP22>3.0.CO;2-Q ER -
@article{ author = "Kostić Rajačić, Slađana and Šoškić, Vukić and Joksimovic, J", year = "1998", abstract = "A series of substituted 4-[2-(5-benzimidazole)ethyl]-arylpiperazines was synthesized by introducing different substituents into position 2 of benzimidazole ring of 4-[2-(N,N-di-n-propylamino)ethyl]-1,2-diaminobenzenes. They were evaluated for in vitro binding affinity at the D 1 and D 2 dopamine and 5-HT(1A) serotonin receptors using synaptosomal membranes of the bovine caudate nuclei and hippocampi, respectively. Tritiated SCH 23390 (D 1 receptor-selective), spiperone (D 2 receptor selective),and 8-OH-DPAT (5-HT(1A) receptor selective) were employed as the radioligands. Only compound 6 expressed a moderate binding affinity at the dopamine D 1 receptor, while the remaining ligands were inefficient or weak competitors of [ 3 H]SCH 23390. Compound 12 was an absolutely inactive competitor of all three radioligands. Also, compound 7 was an inefficient displacer of [ 3 H]-8-OH-DPAT. Compound 19 with a K(i) value of 3.5 nM was the most potent competitor of [ 3 H]spiperone and compound 13 (K(i) = 3.3 nM) was the most efficient in displacing [ 3 H]-8-OH-DPAT from the 5-HT(1A) serotonin receptor. Ligands 5, 6, 8-11, and 13-20 expressed mixed dopaminergic/serotonergic activity in nanomolar range of concentrations with varying affinity ratios which strongly depended on the properties of the substituents introduced into position 2 of benzimidazole ring of the parent compounds.", publisher = "Wiley-VCH Verlag", journal = "Archiv der Pharmazie", title = "Mixed dopaminergic/serotonergic properties of several 2-substituted 4-[2-(5-benzimidazole)ethyl]-1-arylpiperazines", volume = "331", number = "1", pages = "22-26", doi = "10.1002/(SICI)1521-4184(199801)331:1<22::AID-ARDP22>3.0.CO;2-Q" }
Kostić Rajačić, S., Šoškić, V.,& Joksimovic, J.. (1998). Mixed dopaminergic/serotonergic properties of several 2-substituted 4-[2-(5-benzimidazole)ethyl]-1-arylpiperazines. in Archiv der Pharmazie Wiley-VCH Verlag., 331(1), 22-26. https://doi.org/10.1002/(SICI)1521-4184(199801)331:1<22::AID-ARDP22>3.0.CO;2-Q
Kostić Rajačić S, Šoškić V, Joksimovic J. Mixed dopaminergic/serotonergic properties of several 2-substituted 4-[2-(5-benzimidazole)ethyl]-1-arylpiperazines. in Archiv der Pharmazie. 1998;331(1):22-26. doi:10.1002/(SICI)1521-4184(199801)331:1<22::AID-ARDP22>3.0.CO;2-Q .
Kostić Rajačić, Slađana, Šoškić, Vukić, Joksimovic, J, "Mixed dopaminergic/serotonergic properties of several 2-substituted 4-[2-(5-benzimidazole)ethyl]-1-arylpiperazines" in Archiv der Pharmazie, 331, no. 1 (1998):22-26, https://doi.org/10.1002/(SICI)1521-4184(199801)331:1<22::AID-ARDP22>3.0.CO;2-Q . .