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

Abstract

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.