Novel 5-[2-(N,N-di-n-propylamino)-ethyl]benzimidazole-derived high affinity dopaminergic ligands
Апстракт
Derivatives of a noncatechol dopamine (DA) bioisostere 5-[2-(N,N-di-n-propylamino)ethyl]-benzimidazole (15) were synthesized and checked for affinity towards D-1 and D-2 DA receptors (DAR). Ten compounds were obtained by introducing groups of different inductive effects into position 2 of the parent compound 15, while two other compounds were synthesized by introducing a 1-naphthyl group into the side chain of dichloromethyl (9) and dibromomethyl (10) derivatives of 15. The affinity and selectivity of these novel compounds for the D-1 and D-2 class of the DAR were estimated by in vitro competition binding assays using synaptosomal membranes of the bovine caudate nuclei and [ 3 H]SCH 23390 (D-1 selective) and [ 3 H]spiperone (D-2 selective) as radioligands. None of the synthesized compounds expressed the affinity for the binding to D-1 receptors, while compounds 13, 14, 10, 9, 7 and 8, in this rank order of potencies competed with [ 3 H]spiperone binding to D-2 receptors under condition...s of prevented radioligand binding to serotonin 5HT 2 receptors. Their affinities for this class of the DAR were about 2- to 555-fold higher in comparison to the parent compound 15, thus suggesting that some of them could be successfully used as dopaminergic ligands.
Извор:
Pharmazie, 1996, 51, 10, 694-697Издавач:
- Govi-Verlag Pharmazeutischer Verlag GmbH
Институција/група
IHTMTY - JOUR AU - Dragović, D AU - Kostić Rajačić, Slađana AU - Šoškić, Vukić AU - Joksimović, J PY - 1996 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/2832 AB - Derivatives of a noncatechol dopamine (DA) bioisostere 5-[2-(N,N-di-n-propylamino)ethyl]-benzimidazole (15) were synthesized and checked for affinity towards D-1 and D-2 DA receptors (DAR). Ten compounds were obtained by introducing groups of different inductive effects into position 2 of the parent compound 15, while two other compounds were synthesized by introducing a 1-naphthyl group into the side chain of dichloromethyl (9) and dibromomethyl (10) derivatives of 15. The affinity and selectivity of these novel compounds for the D-1 and D-2 class of the DAR were estimated by in vitro competition binding assays using synaptosomal membranes of the bovine caudate nuclei and [ 3 H]SCH 23390 (D-1 selective) and [ 3 H]spiperone (D-2 selective) as radioligands. None of the synthesized compounds expressed the affinity for the binding to D-1 receptors, while compounds 13, 14, 10, 9, 7 and 8, in this rank order of potencies competed with [ 3 H]spiperone binding to D-2 receptors under conditions of prevented radioligand binding to serotonin 5HT 2 receptors. Their affinities for this class of the DAR were about 2- to 555-fold higher in comparison to the parent compound 15, thus suggesting that some of them could be successfully used as dopaminergic ligands. PB - Govi-Verlag Pharmazeutischer Verlag GmbH T2 - Pharmazie T1 - Novel 5-[2-(N,N-di-n-propylamino)-ethyl]benzimidazole-derived high affinity dopaminergic ligands VL - 51 IS - 10 SP - 694 EP - 697 UR - https://hdl.handle.net/21.15107/rcub_cer_2832 ER -
@article{ author = "Dragović, D and Kostić Rajačić, Slađana and Šoškić, Vukić and Joksimović, J", year = "1996", abstract = "Derivatives of a noncatechol dopamine (DA) bioisostere 5-[2-(N,N-di-n-propylamino)ethyl]-benzimidazole (15) were synthesized and checked for affinity towards D-1 and D-2 DA receptors (DAR). Ten compounds were obtained by introducing groups of different inductive effects into position 2 of the parent compound 15, while two other compounds were synthesized by introducing a 1-naphthyl group into the side chain of dichloromethyl (9) and dibromomethyl (10) derivatives of 15. The affinity and selectivity of these novel compounds for the D-1 and D-2 class of the DAR were estimated by in vitro competition binding assays using synaptosomal membranes of the bovine caudate nuclei and [ 3 H]SCH 23390 (D-1 selective) and [ 3 H]spiperone (D-2 selective) as radioligands. None of the synthesized compounds expressed the affinity for the binding to D-1 receptors, while compounds 13, 14, 10, 9, 7 and 8, in this rank order of potencies competed with [ 3 H]spiperone binding to D-2 receptors under conditions of prevented radioligand binding to serotonin 5HT 2 receptors. Their affinities for this class of the DAR were about 2- to 555-fold higher in comparison to the parent compound 15, thus suggesting that some of them could be successfully used as dopaminergic ligands.", publisher = "Govi-Verlag Pharmazeutischer Verlag GmbH", journal = "Pharmazie", title = "Novel 5-[2-(N,N-di-n-propylamino)-ethyl]benzimidazole-derived high affinity dopaminergic ligands", volume = "51", number = "10", pages = "694-697", url = "https://hdl.handle.net/21.15107/rcub_cer_2832" }
Dragović, D., Kostić Rajačić, S., Šoškić, V.,& Joksimović, J.. (1996). Novel 5-[2-(N,N-di-n-propylamino)-ethyl]benzimidazole-derived high affinity dopaminergic ligands. in Pharmazie Govi-Verlag Pharmazeutischer Verlag GmbH., 51(10), 694-697. https://hdl.handle.net/21.15107/rcub_cer_2832
Dragović D, Kostić Rajačić S, Šoškić V, Joksimović J. Novel 5-[2-(N,N-di-n-propylamino)-ethyl]benzimidazole-derived high affinity dopaminergic ligands. in Pharmazie. 1996;51(10):694-697. https://hdl.handle.net/21.15107/rcub_cer_2832 .
Dragović, D, Kostić Rajačić, Slađana, Šoškić, Vukić, Joksimović, J, "Novel 5-[2-(N,N-di-n-propylamino)-ethyl]benzimidazole-derived high affinity dopaminergic ligands" in Pharmazie, 51, no. 10 (1996):694-697, https://hdl.handle.net/21.15107/rcub_cer_2832 .