Synthesis, dopamine D2 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
作者： V. Šukalović , Deana Andrić , G. Roglić , Sladjana Kostić-Rajačić , A. Schrattenholz
DOI: 10.1016/J.EJMECH.2004.10.006
关键词:
摘要: Abstract 5-[3-(4-Arylpiperazin-1-yl)propyl]-1 H -benzimidazoles and 5-[2-(4-arylpiperazin-1-yl)ethoxy]-1 were synthesized their affinity for the D 1 , 2 5-HT 1A receptors examined. They expressed a rather high dopamine receptor. The main features of ligand–D receptor interactions revealed by docking analyses were: salt bridge between piperazine ring protonated N Asp 86, hydrogen bonds ligand bezimidazole part with Ser 141, 122 His 189, edge-to-face arylpiperazine aromatic Phe 178, Tyr 216 Trp 182 bond ethereal oxygen in ethylenoxy ligands 185 or 115. most active 5-{2-[4-(2-methoxyphenyl)-piperazin-1-yl]ethoxy}-1,3-dihydro-2 -benzimidazole-2-thione (27) has maximal number attractive interactions. A satisfactory correlation compounds into competition binding results was observed.
elsevier.com
sci-hub.se 参考文章(23)
Rangaesh Gadasalli, Sandra Aquino, Karl S. Burgoyne, Jambur Ananth, How do the atypical antipsychotics work Journal of Psychiatry & Neuroscience. ,vol. 26, pp. 385- 394 ,(2001)
Gary Remington, Understanding antipsychotic "atypicality": a clinical and pharmacological moving target. Journal of Psychiatry & Neuroscience. ,vol. 28, pp. 275- 284 ,(2003)
Gautam R. Desiraju, The C-h···o hydrogen bond: structural implications and supramolecular design. Accounts of Chemical Research. ,vol. 29, pp. 441- 449 ,(1996) , 10.1021/AR950135N
Johanna Klocker, Alfred Karpfen, Peter Wolschann, Surprisingly regular structure–property relationships between C–O bond distances and methoxy group torsional potentials: An ab initio and density functional study Journal of Molecular Structure: THEOCHEM. ,vol. 635, pp. 141- 150 ,(2003) , 10.1016/S0166-1280(03)00413-5
Johanna Klocker, Alfred Karpfen, Peter Wolschann, On the structure and torsional potential of trifluoromethoxybenzene: an ab initio and density functional study Chemical Physics Letters. ,vol. 367, pp. 566- 575 ,(2003) , 10.1016/S0009-2614(02)01786-4
Goran Roglic, Deana Andric, Sladjana Kostic-Rajacic, Sladjana Dukic, Vukic Šošakic, Introduction of a methyl group in α‐ or β‐position of 1‐heteroarylethyl‐4‐phenyl‐piperazines affects their dopaminergic/serotonergic properties Archiv Der Pharmazie. ,vol. 334, pp. 375- 380 ,(2001) , 10.1002/1521-4184(200112)334:12<375::AID-ARDP375>3.0.CO;2-P
V. ŠOŠKIČ, A. MAELICKE, GORICA PETROVIC, BILJANA RISTIC, JELENA PETROVIČ, Synthesis of some phenothiazine derivatives as potential affinity ligands for the central dopamine receptors. Journal of Pharmacy and Pharmacology. ,vol. 43, pp. 27- 30 ,(2011) , 10.1111/J.2042-7158.1991.TB05442.X
V. Šukalović, Deana Andrić, G. Roglić, Sladjana Kostić-Rajacčić, V. Šoškić, Electrostatic Surface Potential Calculation on Several New Halogenated Benzimidazole‐like Dopaminergic Ligands Archiv Der Pharmazie. ,vol. 337, pp. 376- 382 ,(2004) , 10.1002/ARDP.200300846
Vladimir Šukalović, Mario Zlatović, Deana Andrić, Goran Roglić, Sladjana Kostić-Rajacčić, Vukić Šoškić, Modeling of the D2 dopamine receptor arylpiperazine binding site for 1-[2-[5-(1H-benzimidazole-2-thione)]ethyl]-4-arylpiperazines. Archiv Der Pharmazie. ,vol. 337, pp. 502- 512 ,(2004) , 10.1002/ARDP.200400901
Eric S. Meadows, Stephen L. De Wall, Leonard J. Barbour, Frank R. Fronczek, Min-Sook Kim, George W. Gokel, Structural and Dynamic Evidence for C−H···O Hydrogen Bonding in Lariat Ethers: Implications for Protein Structure Journal of the American Chemical Society. ,vol. 122, pp. 3325- 3335 ,(2000) , 10.1021/JA9940672