TY - JOUR
T1 - 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
AU - Murugesan, Arul
AU - Singh, Thishana
AU - Rajamanikandan, Ramar
AU - Vinu, Madhan
AU - Ilanchelian, Malaichamy
AU - Lin, Chia Her
AU - Gengan, Robert Moonsamy
N1 - Funding Information:
The authors gratefully acknowledge the Durban University of Technology (DUT) for the financial support. All computations were carried out using the computational cluster resources at the Centre for High Performance Computing (CHPC), Cape Town, South Africa.
Publisher Copyright:
© 2020
PY - 2021/1/5
Y1 - 2021/1/5
N2 - 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.
AB - 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.
KW - DFT
KW - HSA protein
KW - Michael reaction
KW - Molecular docking
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U2 - 10.1016/j.molstruc.2020.129260
DO - 10.1016/j.molstruc.2020.129260
M3 - Article
AN - SCOPUS:85090909341
SN - 0022-2860
VL - 1223
JO - Journal of Molecular Structure
JF - Journal of Molecular Structure
M1 - 129260
ER -