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Title: Structural determinants influencing halogen bonding : a case study on azinesulfonamide analogs of aripiprazole as 5-HT1A, 5-HT7, and D2 receptor ligands
Authors: Marciniec, Krzysztof
Kurczab, Rafał
Książek, Maria
Bębenek, Ewa
Chrobak, Elwira
Satała, Grzegorz
Bojarski, Andrzej J.
Kusz, Joachim
Zajdel, Paweł
Keywords: Aripiprazole; Azinesulfonamides; Crystal structure; Halogen bond; Long-chain arylpiperazine
Issue Date: 2018
Citation: Chemistry Central Journal, Vol. 12, iss. 1 (2018), art. no. 55
Abstract: A series of azinesulfonamide derivatives of long-chain arylpiperazines with variable-length alkylene spacers between sulfonamide and 4-arylpiperazine moiety is designed, synthesized, and biologically evaluated. In vitro methods are used to determine their affinity for serotonin 5-HT1A, 5-HT6, 5-HT7, and dopamine D2 receptors. X-ray analysis, two-dimensional NMR conformational studies, and docking into the 5-HT1A and 5-HT7 receptor models are then conducted to investigate the conformational preferences of selected serotonin receptor ligands in different environments. The bent conformation of tetramethylene derivatives is found in a solid state, in dimethyl sulfoxide, and as a global energy minimum during conformational analysis in a simulated water environment. Furthermore, ligand geometry in top-scored complexes is also bent, with one torsion angle in the spacer (τ2) in synclinal conformation. Molecular docking studies indicate the role of halogen bonding in complexes of the most potent ligands and target receptors.[
Description: This work was supported by Grant KNW-1-015/K/7/O from Medical University of Silesia, Katowice, Poland. Calculations have been carried out using resources provided by Wroclaw Centre for Networking and Supercomputing (, Grant No. 382.
DOI: 10.1186/s13065-018-0422-5
ISSN: 1752-153X
Appears in Collections:Artykuły (WNŚiT)

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