Synthesis, dopamine D-2 receptor binding studies and docking analysis of 5-[3-(4-arylpiperazin-1-yl)propyl]-1H-benzimidazole, 5-[2-(4-arylpiperazin-1-yl)ethoxy]-1H-benzimidazole and their analogs
Само за регистроване кориснике
2005
Аутори
Šukalović, Vladimir
Andrić, Deana

Roglić, Goran

Kostić Rajačić, Slađana

Schrattenholz, A
Šoškić, Vukić

Чланак у часопису (Објављена верзија)

Метаподаци
Приказ свих података о документуАпстракт
5-[3-(4-Arylpiperazin-1-yl)propyl]-1H-benzimidazoles and 5-[2-(4-aryipiperazin-1-yl)ethoxy]-1H-benzimidazoles were synthesized and their affinity for the D-1, D-2 and 5-HT1A, receptors examined. They expressed a rather high affinity for the D-2 doparnine receptor. The main features of ligand-D-2 receptor interactions revealed by docking analyses were: salt bridge between piperazine ring protonated N-1 and Asp 86, hydrogen bonds of ligand bezimidazole part with Ser 141, Ser 122 and His 189, edge-to-face interactions of arylpiperazine aromatic ring with Phe 178, Tyr 216 and Trp 182 and hydrogen bond between ethereal oxygen in ethylenoxy ligands and hydrogen of Phe 185 or Trp 115. The most active 5-{2-[4-(2-methoxyphenyl)-piperazin-1-yl]ethoxy}-1,3-di hydro-2H-benzimidazole-2-thione (27) has a maximal number of attractive interactions. A satisfactory correlation between docking of the compounds into the D-2 receptor and competition binding results was observed.
Кључне речи:
arylpiperazines / D2 receptor / 5-HT1A receptor / binding pocket / docking analysisИзвор:
European Journal of Medicinal Chemistry, 2005, 40, 5, 481-493Издавач:
- Editions Scientifiques Medicales Elsevier, Paris
DOI: 10.1016/j.ejmech.2004.10.006
ISSN: 0223-5234
PubMed: 15893022
WoS: 000230243200007
Scopus: 2-s2.0-18844409842
Институција/група
IHTMTY - JOUR AU - Šukalović, Vladimir AU - Andrić, Deana AU - Roglić, Goran AU - Kostić Rajačić, Slađana AU - Schrattenholz, A AU - Šoškić, Vukić PY - 2005 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/182 AB - 5-[3-(4-Arylpiperazin-1-yl)propyl]-1H-benzimidazoles and 5-[2-(4-aryipiperazin-1-yl)ethoxy]-1H-benzimidazoles were synthesized and their affinity for the D-1, D-2 and 5-HT1A, receptors examined. They expressed a rather high affinity for the D-2 doparnine receptor. The main features of ligand-D-2 receptor interactions revealed by docking analyses were: salt bridge between piperazine ring protonated N-1 and Asp 86, hydrogen bonds of ligand bezimidazole part with Ser 141, Ser 122 and His 189, edge-to-face interactions of arylpiperazine aromatic ring with Phe 178, Tyr 216 and Trp 182 and hydrogen bond between ethereal oxygen in ethylenoxy ligands and hydrogen of Phe 185 or Trp 115. The most active 5-{2-[4-(2-methoxyphenyl)-piperazin-1-yl]ethoxy}-1,3-di hydro-2H-benzimidazole-2-thione (27) has a maximal number of attractive interactions. A satisfactory correlation between docking of the compounds into the D-2 receptor and competition binding results was observed. PB - Editions Scientifiques Medicales Elsevier, Paris T2 - European Journal of Medicinal Chemistry T1 - Synthesis, dopamine D-2 receptor binding studies and docking analysis of 5-[3-(4-arylpiperazin-1-yl)propyl]-1H-benzimidazole, 5-[2-(4-arylpiperazin-1-yl)ethoxy]-1H-benzimidazole and their analogs VL - 40 IS - 5 SP - 481 EP - 493 DO - 10.1016/j.ejmech.2004.10.006 ER -
@article{ author = "Šukalović, Vladimir and Andrić, Deana and Roglić, Goran and Kostić Rajačić, Slađana and Schrattenholz, A and Šoškić, Vukić", year = "2005", abstract = "5-[3-(4-Arylpiperazin-1-yl)propyl]-1H-benzimidazoles and 5-[2-(4-aryipiperazin-1-yl)ethoxy]-1H-benzimidazoles were synthesized and their affinity for the D-1, D-2 and 5-HT1A, receptors examined. They expressed a rather high affinity for the D-2 doparnine receptor. The main features of ligand-D-2 receptor interactions revealed by docking analyses were: salt bridge between piperazine ring protonated N-1 and Asp 86, hydrogen bonds of ligand bezimidazole part with Ser 141, Ser 122 and His 189, edge-to-face interactions of arylpiperazine aromatic ring with Phe 178, Tyr 216 and Trp 182 and hydrogen bond between ethereal oxygen in ethylenoxy ligands and hydrogen of Phe 185 or Trp 115. The most active 5-{2-[4-(2-methoxyphenyl)-piperazin-1-yl]ethoxy}-1,3-di hydro-2H-benzimidazole-2-thione (27) has a maximal number of attractive interactions. A satisfactory correlation between docking of the compounds into the D-2 receptor and competition binding results was observed.", publisher = "Editions Scientifiques Medicales Elsevier, Paris", journal = "European Journal of Medicinal Chemistry", title = "Synthesis, dopamine D-2 receptor binding studies and docking analysis of 5-[3-(4-arylpiperazin-1-yl)propyl]-1H-benzimidazole, 5-[2-(4-arylpiperazin-1-yl)ethoxy]-1H-benzimidazole and their analogs", volume = "40", number = "5", pages = "481-493", doi = "10.1016/j.ejmech.2004.10.006" }
Šukalović, V., Andrić, D., Roglić, G., Kostić Rajačić, S., Schrattenholz, A.,& Šoškić, V.. (2005). Synthesis, dopamine D-2 receptor binding studies and docking analysis of 5-[3-(4-arylpiperazin-1-yl)propyl]-1H-benzimidazole, 5-[2-(4-arylpiperazin-1-yl)ethoxy]-1H-benzimidazole and their analogs. in European Journal of Medicinal Chemistry Editions Scientifiques Medicales Elsevier, Paris., 40(5), 481-493. https://doi.org/10.1016/j.ejmech.2004.10.006
Šukalović V, Andrić D, Roglić G, Kostić Rajačić S, Schrattenholz A, Šoškić V. Synthesis, dopamine D-2 receptor binding studies and docking analysis of 5-[3-(4-arylpiperazin-1-yl)propyl]-1H-benzimidazole, 5-[2-(4-arylpiperazin-1-yl)ethoxy]-1H-benzimidazole and their analogs. in European Journal of Medicinal Chemistry. 2005;40(5):481-493. doi:10.1016/j.ejmech.2004.10.006 .
Šukalović, Vladimir, Andrić, Deana, Roglić, Goran, Kostić Rajačić, Slađana, Schrattenholz, A, Šoškić, Vukić, "Synthesis, dopamine D-2 receptor binding studies and docking analysis of 5-[3-(4-arylpiperazin-1-yl)propyl]-1H-benzimidazole, 5-[2-(4-arylpiperazin-1-yl)ethoxy]-1H-benzimidazole and their analogs" in European Journal of Medicinal Chemistry, 40, no. 5 (2005):481-493, https://doi.org/10.1016/j.ejmech.2004.10.006 . .