Synthesis, spectroscopic characterization, molecular docking studies and DFT calculation of novel Mannich base 1-((4-ethylpiperazin-1-yl)(2-hydroxyphenyl)methyl)naphthalen-2-ol

被引:41
作者
Vennila, P. [1 ]
Venkatesh, G. [2 ]
Sixto-Lopez, Yudibeth [3 ]
Kamal, C. [4 ]
Kaya, S. [5 ]
Serdaroglu, G. [6 ]
Landeros-Rivera, Bruno [7 ]
机构
[1] Thiruvalluvar Govt Arts Coll, Dept Chem, Rasipuram 637401, Tamil Nadu, India
[2] Muthayammal Mem Coll Arts & Sci, Dept Chem, Rasipuram 637408, Tamil Nadu, India
[3] Inst Politecn Nacl, Lab Desarrollo Nuevos Farmacos & Innovac Biotecno, Escuela Super Med, Secc Estudios Posgrad & Invest, Mexico City 11340, DF, Mexico
[4] Mahendra Coll Engn, Dept Chem, Salem 636106, Tamil Nadu, India
[5] Cumhuriyet Univ, Dept Chem, TR-58140 Sivas, Turkey
[6] Sivas Cumhuriyet Univ, Fac Educ Math & Sci Edu, TR-58140 Sivas, Turkey
[7] Sorbonne Univ, Lab Chim Theor, LCT, CNRS, Paris, France
关键词
Mannich base; Molecular geometrical properties; Quantum chemical calculation; Natural bond Orbital; Molecular Docking; MUSCARINIC RECEPTOR SUBTYPES; EMPIRICAL FORCE-FIELD; PROTONATION STATES; NUCLEIC-ACIDS; STEREOSELECTIVITY; DYNAMICS; AMINONAPHTHOL; PROCYCLIDINE; RECOGNITION; SIMULATIONS;
D O I
10.1016/j.molstruc.2021.131164
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A novel Mannich base based compound namely 1-(4-ethylpiperazin-1-yl)(2-hydroxyphenyl)methyl)naphthalene-2-ol (MNP) has been synthesized by a condensation reaction. MNP had been evaluated and characterized by following spectroscopic techniques, FT-IR, FT-Raman, UV and NMR. The MNP fundamental vibrational bands and their intensities have been interpreted with the assistance of optimizations and normal coordinate force field simulations based on density functional theory (DFT) with B3LYP function 6-311++G(d,p) basis set. In addition, the observed bands were compared to the calculated spectral data. The CAM-B3LYP/6-311++G(2df,pd) level calculations were used to look for chemical reactivity trends. The validity of the fundamental electronic structural principles "Maximum Hardness, Minimum Polarizability, and Minimum Electrophilicity" has also been discussed. NCIPLOT4 software was also used to create the NCI isosurfaces, which were then visualized with VMD. The nature of inter and intramolecular hydrogen bonds also been explored using natural bond orbital and Quantum Theory of Atoms in Molecules analysis. According to the MD simulation and molecular docking studies, the synthesized molecule appears to be a potential compound targeting the M1R and DRD2 proteins implicated in many diseases such as Alzheimer's disease, Parkinson's disease and schizophrenia. (C) 2021 Elsevier B.V. All rights reserved.
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页数:17
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