Schiff Bases from α-ionone with Adenine, Cytosine, and l-leucine Biomolecules: Synthesis, Structural Features, Electronic Structure, and Medicinal Activities

Abstract

Tea is a very important source of the terepenoid [Formula: see text]-ionone, which is much appreciated as a medicinal beverage. Schiff bases are a very important class of organic compounds usually formed by the condensation of carbonyl compounds with amines. [Formula: see text]-ionone is a carbonyl terpenoid obtained from Schiff bases on condensation with nucleobases like adenine and cytosine and the amino acid [Formula: see text]-leucine. We synthesized these three Schiff bases and characterized them using UV, FTIR, and H1 and C13-NMR spectra. The molecules were optimized using B3LYP/6-311+G(2d,p) level followed by the simulation of FT-IR spectra, of which the simulated and experimental spectra showed complete agreement. The UV spectra were simulated using TD-DFT, and the electronic excitations were carefully analyzed. Natural bond orbitals provided an analysis of the stability of the compound, which is supplemented by the data from frontier molecular orbital analysis. Detailed wavefunction analysis is reported which predicts the active centers, reactivity profile, and the extent of non-covalent interactions. PASS indicated that compounds show antieczemic properties and antiarthritic properties, which is confirmed with the help of molecular docking results.

Structural variety of Cu (II), Ni (II), and Co (II) complexes of a hydrazone based on 5‐acetyl‐4‐hydroxy‐2H‐1,3‐thiazine‐2,6(3H)‐dione: Synthesis, spectroscopic, density functional theory, antitumor, and docking studies

“…[15] These ligands, as well as their metal complexes, possess antibacterial, [16] antifungal, [17] and antitumour activities. [18] Thiazines are very useful units in the fields of medicinal and pharmaceutical chemistry due to their antimicrobial, [19] anticancer, [20] potential antiinflammatory agents, [21] and antiproliferative activities. [22] Transition metal compounds are crucial to redox enzyme systems and bio-inorganic chemistry.…”

“…Thiazines are very useful units in the fields of medicinal and pharmaceutical chemistry due to their antimicrobial, [ 19 ] anticancer, [ 20 ] potential anti‐inflammatory agents, [ 21 ] and antiproliferative activities. [ 22 ]…”

Synthesis, spectral features, electronic structure studies, and molecular docking analysis of a Schiffbase (E)‐1‐(4‐chlorophenyl)‐N‐(nitrophenyl)methanimine from 4‐chloroaniline and 2‐nitrobenzaldehyde

“…[10] Schiff bases derived from 2nitrobenzaldehyde can be altered to manufacture chitosan which is a promising drug used to clot blood and had various biomedical and drug delivery applications. [11][12][13][14][15][16] Because of great significance in the chemistry of Schiff bases obtained from 4-chloroaniline and 2nitrobenzaldehyde, we are intended to inquire the synthesis of compound 4-chlorophenyl-2nitrobenzylidene amine and its characterization employing FTIR, 1 H NMR, and 13 C NMR both theoratically and experimentally. In adition, we scrutinize various photophysical properties with the support of DFT/B3LYP/cc-pVDZ techniques and other experimental techniques.…”

“…[ 10 ] Schiff bases derived from 2‐nitrobenzaldehyde can be altered to manufacture chitosan which is a promising drug used to clot blood and had various biomedical and drug delivery applications. [ 11–16 ]…”