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. 2022 Nov 23;27(23):8150.
doi: 10.3390/molecules27238150.

A New MBH Adduct as an Efficient Ligand in the Synthesis of Metallodrugs: Characterization, Geometrical Optimization, XRD, Biological Activities, and Molecular Docking Studies

Shazia Ishfaq  1 , Shazia Nisar  1 , Sadaf Iqbal  1 , Saqib Ali  2 , Syed Tariq Ali  1 , ElSayed Din  3 , Norah Salem Alsaiari  4 , Kholood A Dahlous  5 , Muhammad Sufyan Javed  6 , Patrizia Bocchetta  7
Affiliations

A New MBH Adduct as an Efficient Ligand in the Synthesis of Metallodrugs: Characterization, Geometrical Optimization, XRD, Biological Activities, and Molecular Docking Studies

Shazia Ishfaq et al. Molecules. .

Abstract

This article reports the synthesis, characterization, geometrical optimization, and biological studies of new MBH-based organometallic compounds of medicinal significance. The ligand (MNHA) was prepared via the Morita-Baylis-Hillman (MBH) synthetic route, from aromatic aldehyde containing multiple functional groups. Metal complexes were prepared in an alkaline medium and under other suitable reaction conditions. Spectral and elemental analyses were used to identify the structural and molecular formulas of each compound. Optimized geometry was determined through density functional theory (DFT) B3LYP and 6-311++ G (d,p) basis set for the MBH adduct, whereas structures of novel complexes were optimized with the semi-empirical PM6 method. Powder XRD analysis furnished the crystal class of complexes, with Co3+, Cr3+, and Mn2+ being cubic, while Ni2+ was hexagonal, and Cu2+ was orthorhombic. Moreover, the ligand, along with Ni2+ and Co3+ complexes, showed profound antibacterial action against S. aureus, E. coli, B. pumilis, and S. typhi. Additionally, all of the complexes were shown to persist in the positive antioxidant potential of the ligand. Contrarily, not a single metal complex conserved the antifungal potentials of the ligand.

Keywords: MBH adduct; XRD; biological studies; geometrical optimization; metal complexes.

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Conflict of interest statement

There are no conflict of interest declared by all authors.

Figures

Scheme 1
Scheme 1
General scheme of Morita–Baylis–Hillman reaction with tertiary amine as a catalyst at room temperature and other reaction conditions.
Scheme 2
Scheme 2
Methodology adapted for syntheses of compounds 4–8.
Figure 1
Figure 1
FT-IR theoretical spectrum of methyl 2-((2-nitrophenyl)(hydroxyl)methyl) acrylate (MNHA).
Figure 2
Figure 2
FT-IR experimental spectrum of methyl 2-((2-nitrophenyl)(hydroxyl)methyl) acrylate (MNHA).
Figure 3
Figure 3
FT-IR overlay patterns of compounds 3–8.
Figure 4
Figure 4
Theoretically optimized geometries of compounds 3–8. (a) [(MNHA)], (b) [Cr(MNHA)2]+, (c) [Co(MNHA)2]+, (d) [Ni(MNHA)2], (e) [Mn(MNHA)2], and (f) [Cu(MNHA)2]. The stable geometries confirmed each metal coordinated octahedrally with two tridentate ligand molecules.
Figure 5
Figure 5
XRD powder diffraction patterns of compounds 4–8.
Figure 6
Figure 6
Comparative histograms of compounds 3–8 (S.typhi, E.coli = Gram-negative bacteria and B.subtilis, S.aureus = Gram-positive bacteria) in terms of % inhibition zone.
Figure 7
Figure 7
Graphical representation of antioxidant activities of ascorbic acid (standard).
Figure 8
Figure 8
Graphical representation of antioxidant activities of MNHA and its corresponding metal complexes.
Figure 9
Figure 9
Antifungal activity of MNHA. Inhibition of mycelial growth (%) = Δd/dc × 100 (Δd = dc − dt); dc = average diameter of fungal colony in negative the control, while dt = average diameter of fungal colony in experimental plates.
Figure 10
Figure 10
The binding conformations of the MNHA ligand against (A) S. typhi, (B) S. aureaus, and (C) E. coli.
Figure 11
Figure 11
The binding conformations of ligand (MNHA) metal complexes against (A,D) E. coli, (B,E) S. typhi, and (C,F) S. aureaus.
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