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. 2021 Aug 6;7(8):e07724.
doi: 10.1016/j.heliyon.2021.e07724. eCollection 2021 Aug.

Synthesis, single crystal (XRD), Hirshfeld surface analysis, computational study (DFT) and molecular docking studies of (E)-4-((2-hydroxy-3,5-diiodobenzylidene)amino)-N-(pyrimidine)-2-yl) benzenesulfonamide

N Elangovan  1 , S Sowrirajan  2
Affiliations

Synthesis, single crystal (XRD), Hirshfeld surface analysis, computational study (DFT) and molecular docking studies of (E)-4-((2-hydroxy-3,5-diiodobenzylidene)amino)-N-(pyrimidine)-2-yl) benzenesulfonamide

N Elangovan et al. Heliyon. .

Abstract

The Schiff base (E)-4-((2-hydroxy-3,5-diiodobenzylidene)amino)-N-(pyrimidine)-2-yl) benzene sulfonamide (DIDA) compound was synthesis with condensation of 3,5-diiodosalicylaldehyde and sulfadiazine. The compound characterized with FTIR, X-ray crystallography and electronic spectra. The titled compound associated with experimental and theoretical method, DFT used for the theoretical method. The IR was calculated from DFT mode with B3LYP/GENSEP basic set. The electronic spectra computed from TD-DFT method with CAM-B3LYP functional, with IEFPCM solvation model and DMSO used as the solvent. Wave function based properties like localized orbital locator, electron localization function and non-covalent interactions have been studied extensively. The ADMET properties of the compound DIDA indicated that the compound has excellent drug likeness properties and PASS studies showed that it has anti-infective properties, which is confirmed by a docking score of -7.4 kcal/mol.

Keywords: DFT; Drug-likeness; Molecular docking; Single crystal; Sulfadiazine; Synthesis.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Synthesis of (E)-4-((2-hydroxy-3,5-diiodobenzylidene)amino)-N-(pyrimidine)-2-yl) benzene sulfonamide (DIDA).
Figure 2
Figure 2
(a) ORTEP (b) optimized structure of the (E)-4-((2-hydroxy-3,5-diiodobenzylidene)amino)-N-(pyrimidine)-2-yl) benzene sulfonamide (DIDA).
Figure 3
Figure 3
Crystal packing diagram of (E)-4-((2-hydroxy-3,5-diiodobenzylidene)amino)-N-(pyrimidine)-2-yl) benzene sulfonamide.
Figure 4
Figure 4
Hirshfeld surface map (a) dnorm, (b) di, (c) de, (d) Shape index, (e) Curvedness and (f) Fragment path of the compound (E)-4-((2-hydroxy-3,5-diiodobenzylidene)amino)-N-(pyrimidine)-2-yl) benzene sulfonamide (DIDA).
Figure 5
Figure 5
Two dimensional fingerprint plot of the compound (E)-4-((2-hydroxy-3,5-diiodobenzylidene) amino)-N-(pyrimidine)-2-yl) benzene sulfonamide (DIDA).
Figure 6
Figure 6
Experimental and calculated FTIR spectra of (E)-4-((2-hydroxy-3,5-diiodobenzylidene) amino)-N-(pyrimidine)-2-yl) benzene sulfonamide (DIDA).
Figure 7
Figure 7
HOMO-LUMO energy diagram of the compound (E)-4-((2-hydroxy-3,5-diiodobenzylidene) amino)-N-(pyrimidine)-2-yl) benzene sulfonamide (DIDA).
Figure 8
Figure 8
Molecular electrostatic potential (a) color filled surface map (b) counter line map of (E)-4-((2-hydroxy-3,5-diiodobenzylidene) amino)-N-(pyrimidine)-2-yl) benzene sulfonamide.
Figure 9
Figure 9
Electronic spectra of (E)-4-((2-hydroxy-3,5-diiodobenzylidene) amino)-N-(pyrimidine) -2-yl) benzene sulfonamide (DIDA).
Figure 10
Figure 10
Localized orbital locator map of (E)-4-((2-hydroxy-3,5-diiodobenzylidene) amino)-N-(pyrimidine)-2-yl) benzene sulfonamide.
Figure 11
Figure 11
Electron localized function map of (E)-4-((2-hydroxy-3,5-diiodobenzylidene) amino)-N-(pyrimidine)-2-yl) benzene sulfonamide.
Figure 12
Figure 12
RDG (non-covalent interaction) map of (E)-4-((2-hydroxy-3,5-diiodobenzylidene) amino)-N-(pyrimidine)-2-yl) benzene sulfonamide.
Figure 13
Figure 13
Protein ligand interaction site (a) 2D diagram (b) interaction site of (E)-4-((2-hydroxy-3,5-diiodobenzylidene) amino)-N-(pyrimidine)-2-yl) benzene sulfonamide.
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