Synthesis, spectroscopic, DFT, HSA binding and docking studies of new 1,5-bis(4-chlorophenyl)-3-(2-(4-methylpiperazin-1-yl)quinolin-3yl)pentan e-1,5-dione
- Authors
- Murugesan, Arul; Singh, Thishana; Rajamanikandan, Ramar; Vinu, Madhan; Ilanchelian, Malaichamy; Lin, Chia-Her; Gengan, Robert Moonsamy
- Issue Date
- Jan-2021
- Publisher
- ELSEVIER
- Keywords
- Michael reaction; DFT; HSA protein; Molecular docking
- Citation
- JOURNAL OF MOLECULAR STRUCTURE, v.1223
- Journal Title
- JOURNAL OF MOLECULAR STRUCTURE
- Volume
- 1223
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/84576
- DOI
- 10.1016/j.molstruc.2020.129260
- ISSN
- 0022-2860
- 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, H-1-NMR, C-13-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: E-HOMO = -6.015 eV, E-LUMO = 2.525 eV and energy gap, similar to E-gap = 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 similar to G 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). (C) 2020 Elsevier B.V. All rights reserved.
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