Synthesis, Crystal Structure, Hirshfeld Surface Analysis, DNA/BSA Interaction and Molecular Docking Studies of 2-(6-(4-chlorophenyl)-1,2,4-triazin-3-yl)quinoline

• Published in: Journal of molecular structure Vol. 1292; p. 136128
• Main Authors: Göktürk, Tolga, Zengin, Talip, Hökelek, Tuncer, Topkaya, Cansu Gökçe, Güp, Ramazan
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15-11-2023
• Subjects: 1,2,4-triazine; BSA binding; DNA binding; Hirshfeld surface analysis; Molecular docking; Hirshfeld surface analysis; 1,2,4-triazine; BSA binding; DNA binding; Molecular docking
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2023.136128

•A new 1,2,4-triazine derivative was synthesized using quinoline moiety.•Structure of compound was confirmed by different spectral techniques and X-ray crystallograpy.•The Hirshfeld surface analysis, interaction energy calculations and energy frameworks of compound was explored.•DNA and BSA binding activities of compound were investigated.•Molecular docking for the synthesized compound were performed.
We reported herein a new 1,2,4-triazine derivative, 2-(6-(4-chlorophenyl)-1,2,4-triazin-3-yl)quinoline, synthesized by cyclization of p‑chloro isonitrosophenylhydrazine with 2-quinolinecarboxaldehyde. Its structure was elucidated by FTIR, 1H NMR, 13C APT NMR, elemental analyses, and also its molecular and crystal structures were determined by single crystal X-ray analysis which revealed that the compound was crystallized in monoclinic system P 2/c space group with a = 17.2564 (6) Å, b = 6.0419 (3) Å, c = 14.4093 (5) Å, β = 103.469 (3)°, Z = 4 and V = 1461.01 (10) Å3. The Hirshfeld surface analysis of the crystal structure indicated that the most important contributions for the crystal packing were from H … H (29.2%), H … C/C … H (22.3%), H … N/CN … H (16.1%) and H … CI/CI … H (14.5%) interactions. Hydrogen bonding and van der Waals interactions were the dominant interactions in the crystal packing. The evaluation of the electrostatic, dispersion and total energy frameworks indicated that the stabilization was dominated via the dispersion energy contribution. The synthesized compound was investigated for CT-DNA and BSA binding activity using various in vitro and in silico techniques. Results were revealed that binding of the compound with CT-DNA via minor groove and with BSA via subdomain IIIB.
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