Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: Synthesis, X-ray crystallography, DFT and cytotoxicity studies

Abstract

Six new tin(IV) compounds derived from tridentate dinegatively charged ONS dithiocarbazate Schiff bases derived from 2-hydroxy-3-methoxybenzaldehyde (H 2 L1, H 2 L2 and H 2 L3) and 2,3-dihydroxybenzaldehyde (H 2 L4, H 2 L5 and H 2 L6) (where H 2 Ln = di-acids of Schiff base) are reported. The compounds were characterised by elemental analysis, FT-IR and multinuclear NMR (1 H, 13 C and 119 Sn) spectroscopy. The crystal structures of tin(IV) [S-4-methybenzyl-β-N-(2-hydroxy-3-methoxybenzylmethylene)dithiocarbazate] (2) and tin(IV) [S-benzyl-β-N-(2-hydroxy-3-methoxy benzylmethylene)dithiocarbazate] (3) were determined by X-ray single crystal diffraction analysis. X-ray crystallography showed the molecular geometries in homoleptic 2 and 3 to be quite similar in which the dinegative tridentate ligand coordinated the tin atoms via thiolate-S, phenoxide-O and imine-N atoms. The coordination geometries are based on an octahedron with like-atoms mutually trans. The *Revised Manuscript Click here to view linked References 2 experimental findings were validated by density functional theory (DFT) calculations at the B3LYP/LanL2DZ/6-311G(d,p) level of theory. All the tin(IV) compounds, except the insoluble compound 2 were screened for their in vitro cytotoxicity against a panel ten of cancer cell lines and one normal breast cell line (MCF-10A) by MTT assay. Interestingly, the cytotoxicity of five tin(IV) compounds against HT29, MCF7 and MIA was higher than the reference drug, cisplatin.

Dithiocarbazate Ligand‐Based Cu(II), Ni(II), and Zn(II) Complexes: Synthesis, Structural Investigations, Cytotoxicity, DNA Binding, and Molecular Docking Studies

“…The distances of Ni1-N1 and Ni1–S1 are 1.889 (6) Å and 2.153 (8) Å, respectively, are comparable to the similar constituted complexes such as [Ni (L 3 ) (py)] [Ni-N2 = 1.884 (7) Å, N1-S1 = 2.170 (3) Å] [ 58 ] and NiL 2 1 [N1–Ni1 = 1.9010 (2) Å, Ni1–S1 = 2.2015 (9) Å] [ 57 ]. These bond lengths are marginally shorter than the equivalent bonds in the oxomolybdenum(VI) [ 59 ], tin(IV) [ 60 ], and copper(II) [ 61 ] complexes of related dithiocarbazate ligands. In the crystal packing of 3 , the π - π interactions are the most dominant in stabilizing the structure with the closest separation being 3.823 (5) Å due to the lack of any potential hydrogen bond donor ( Figure 5(a) ).…”

“…9) Å] [57]. ese bond lengths are marginally shorter than the equivalent bonds in the oxomolybdenum(VI) [59], tin(IV) [60], and copper(II) [61] complexes of related dithiocarbazate ligands. In the crystal packing of 3, the π-π interactions are the most dominant in stabilizing the structure with the closest separation being 3.823 (5) Å due to the lack of any potential hydrogen bond donor (Figure 5(a)).…”

Noncovalent Bonds through Sigma and Pi-Hole Located on the Same Molecule. Guiding Principles and Comparisons

“…Quite the opposite from representing exotic or unusual contacts, these bonds make important contributions to numerous fields of chemistry and biology. As examples, understanding the forces behind crystal engineering and supramolecular chemistry benefits from a knowledge of σ-hole interactions due to their directionality, strength, and self-organization properties which promote formation of adducts in the solid state [ 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 , 45 , 46 , 47 , 48 , 49 , 50 , 51 , 52 ]. The importance of σ-hole bonding has also been verified in the context of anion recognition processes [ 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 ], materials chemistry [ 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 ], or biochemistry [ 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 ].…”

Tin(IV) compounds of tridentate thiosemicarbazone Schiff bases: Synthesis, characterization, in-silico analysis and in vitro cytotoxicity

“…As a continuation of our research on tridentate ONS Schiff bases and their tin(IV) compounds [25,26], we report herein the preparation, spectroscopic characterization, and bioactivity of tin(IV) compounds (5-16) containing 2-hydroxy-3-methoxybenzyl-and 2,3-dihydroxybenzylderived thiosemicarbazone Schiff bases (1-4). Diphenyl- (5, 8, 11, and 14) and dimethyltin(IV) (6, 9, 12, and 15) compounds exhibited penta-coordinated geometry whereas tin(IV) compounds were coordinated to two molecules of thiosemicarbazone Schiff bases (7, 10, 13, and 16) suggesting a hexa-coordinated geometry according to 119 Sn NMR analysis.…”