Synthesis, spectroscopic, DFT, HSA binding and docking studies of new 1,5-bis(4-chlorophenyl)-3-(2-(4-methylpiperazin-1-yl)quinolin-3-yl)pentane-1,5-dione

Arul Murugesan, Thishana Singh, Ramar Rajamanikandan, Madhan Vinu, Malaichamy Ilanchelian, Chia Her Lin, Robert Moonsamy Gengan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

1,5-Bis(4-chlorophenyl)-3-(2-(4-methylpiperazin-1-yl)quinolin-3-yl)pentane-1,5-dione was synthesised and characterised using single-crystal X-ray Crystallography, FT-IR, 1H-NMR, 13C-NMR and UV-Visible spectroscopy. DFT calculations were performed at the B3LYP/6-311++G (d.p) level of theory in the gas phase. Frontier Molecular Orbitals (FMO) yielded HOMO-LUMO energy as: EHOMO = -6.015 eV, ELUMO = -2.525 eV and energy gap, ΔEgap = 3.490 eV. Fukui Function Analysis (FFA) indicated the reactive sites for electrophilic, and nucleophilic attack. The molecule's electrophilic addition site is 4-N in the piperazine group with a value of 0.020. The site for nucleophilic attack is both 13-C and 15-C in the quinoline group with values of 0.02 and 0.031 respectively. The biological activity was elucidated by molecular docking studies that gave a ΔG value for HSA binding of -26.44 kJ mol−1 which is approximately similar to the experimental value obtained from emission spectral data of -32.15 kJ mol−1.

Original languageEnglish
Article number129260
JournalJournal of Molecular Structure
Volume1223
DOIs
Publication statusPublished - 2021 Jan 5
Externally publishedYes

Keywords

  • DFT
  • HSA protein
  • Michael reaction
  • Molecular docking

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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