Theoretical Investigation of the Structural, Spectroscopic, Electronic, and Pharmacological Properties of 4-Nerolidylcathecol, an Important Bioactive Molecule

Abstract

4-Nerolidylcatechol (4NRC), a secondary metabolite described as a potent antioxidant that presents anti-inflammatory, antimalarial, analgesic, and cytotoxic properties, has been receiving prominence in the catechol class. In this work, a theoretical DFT study of the vibrational, structural, and quantum properties of 4-nerolidylcatechol (4NRC) using the B3LYP/6-311G (2d,p) level is presented. e theoretical molecular geometry data were compared with the X-ray data of a similar molecule in the associated literature and a conformational study is presented, with the aim of providing a good comprehension of the 4NRC structural arrangement and stability. Also, HOMO-LUMO energy gap and natural bond orbitals (NBOs) were performed and discussed. e calculated UV spectrum showed similarity to the experimentally obtained data, with transitions assigned. e comparative IR studies revealed that intermolecular hydrogen bonds that stabilize dimeric forms are plausible and also allowed the assignment of several characteristic vibrations. Molecular docking calculations with DNA topoisomerase I-DNA complex (TOPO-I), glyceraldehyde 3-phospate dehydrogenase (GAPDH), and Plasmodium falciparum lactate dehydrogenase (PfLDH) showed binding free energies of −6.3, −6.5, and −7.6 kcal/mol, respectively, which indicates that 4NRC is a good competitive inhibitor for these enzymes.

Synthesis, spectroscopic, chemical reactivity, topology analysis and molecular docking study of ethyl 5-hydroxy-2-thioxo-4-(p-tolyl)-6-(trifluoromethyl)hexahydropyrimidine-5-carboxylate

“…The molecular docking (ligand-protein) is commonly used to predict the binding and interactions between small and macro molecule which leads to the treatment of various diseases in the field of molecular structural biology [ [47] , [48] , [49] ]. The values of Pa and Pi named probability for active and inactive are known that predicts Pa >0.700 for a particular disease states that the molecule has an ability to react with the proteins that are used to cure the disease.…”

Isosterism in pyrrole via azaboroles substitution, a theoretical investigation for electronic structural, stability and aromaticity

“…To investigate the electronic structure and reactivity of organic compounds and to calculate the energy gap, this section focuses HOMO and LUMO, which are also known as frontier molecular orbitals (FMO) [ 94 , 95 ]. See Table 4 .…”

Synthesis, Characterization and in vitro, in vivo and in silico Anti-Inflammatory Studies of the Novel Hybrid Based on Ibuprofen and 3-Hydroxy-Copalic Acid Isolated from Copaiba Oil (Copaifera multijuga)

“…RMSD values up to 2 Å are considered reliable for a docking protocol. 12 All the structures used in the docking calculations were modeled in the Gaussian 09 program 13 and optimized at the density functional theory (DFT) level using B3LYP (Becke, 3-parameter, Lee-Yang-Parr) exchange-correlation functional with 6-31G(d) basis set.…”