Molecular aggregations of bicyclodioxazastannone produced from multicomponent reactions involving functionalized 2-hydroxybenzaldehydes, α- or β-amino acids and a dimethyltin precursor

Baul, Tushar S. Basu; Chaurasiya, Anurag; Lyčka, Antonı́n; Rojas-León, Irán; Höpfl, Herbert

doi:10.1016/j.jorganchem.2019.07.010

Cited by 10 publications

(13 citation statements)

References 81 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The 119 Sn NMR signal for compounds 1–5 was observed at −159, −199, −157, −197, and −399 ppm, respectively. [ 25 ] These chemical shifts were in good agreement with the reported shifts for the similar kind of molecules and suggest the formation of penta‐coordinated geometry around the Sn center. The compounds 2 and 4 depicted lower 119 Sn NMR chemical shifts as compared to the compounds 1 and 3 owing to the stronger electron releasing effect of the butyl group bound to the Sn center which shifts the signal more upfield.…”

Section: Resultssupporting

confidence: 84%

“…The Me–Sn–Me bond angle (θ) can be assessed from Lockhart's equations using these coupling constants between the protons of methyl groups and the Sn metal center. [ 24,25 ]

θ (() °) goodbreak= 0.0161 {|J^{2} ({Sn}^{119}, H^{1})|}^{2} goodbreak- 1.32 (||, J^{2} ((),, {Sn}^{119}, {normalH}^{1})) goodbreak+ 133.4,

θ (() °) goodbreak= \frac{((), (||, J^{1} ((),, {Sn}^{119}, {normalC}^{13})) goodbreak+ 875)}{11.4} .

…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Glutamine conjugated organotin(IV) Schiff base compounds: Synthesis, structure, and anticancer properties

Sharma

Agnihotri

Kumar

et al. 2021

Applied Organom Chemis

View full text Add to dashboard Cite

Herein, glutamine conjugated organotin(IV) Schiff base compounds, [(SBGlu‐Naph)Sn (Me)2] (1), [(SBGlu‐Naph)Sn(n‐Bu)2] (2), [(SBGlu‐Sali)Sn (Me)2] (3), [(SBGlu‐Sali)Sn(n‐Bu)2] (4) and [(SBGlu‐Sali)Sn (Ph)2] (5), were synthesized by one‐pot reaction with an aldehyde (2‐hydroxy‐1‐naphthaldehyde) for 1 and 2, and 5‐methyl‐2‐hydroxybenzaldehyde (for 3–5) and respective diorganotin oxide. The compounds were characterized using elemental micro‐analyses, spectroscopic techniques (FT‐IR, 1H NMR, 13C NMR, and 119Sn NMR), mass spectrometry, and single‐crystal X‐ray diffraction analyses. Based on in‐silico ADME (absorption, distribution, metabolism, and excretion) and drug‐likeness properties, compounds 1, 3, and 4 were selected to investigate their DNA/Protein binding properties with calf thymus DNA (CT‐DNA) and bovine serum albumin (BSA) using spectrophotometry and spectrofluorimetry. The intercalative mode of binding with CT‐DNA was supported by molecular docking simulations. The emission spectral data of compounds with CT‐DNA showed 1 as a groove binder, and 3 and 4 as an intercalator which was confirmed by competitive displacement assays. Similarly, static and dynamic mode of interaction between the compounds and BSA was found. Furthermore, these compounds were screened for their cytotoxic activity against two human cancer cell lines; PC‐3 (Prostate) and Mg‐63 (Osteosarcoma) at different concentrations. Quantitative structure–activity relationship (QSAR)‐based regression models were developed and implemented on compounds 1, 3, and 4 that inferred compound 3 to be the most potential candidate for further in vivo studies.

show abstract

Section: Resultssupporting

confidence: 84%

“…The Me–Sn–Me bond angle (θ) can be assessed from Lockhart's equations using these coupling constants between the protons of methyl groups and the Sn metal center. [ 24,25 ]

θ (() °) goodbreak= 0.0161 {|J^{2} ({Sn}^{119}, H^{1})|}^{2} goodbreak- 1.32 (||, J^{2} ((),, {Sn}^{119}, {normalH}^{1})) goodbreak+ 133.4,

θ (() °) goodbreak= \frac{((), (||, J^{1} ((),, {Sn}^{119}, {normalC}^{13})) goodbreak+ 875)}{11.4} .

…”

Section: Resultsmentioning

confidence: 99%

Glutamine conjugated organotin(IV) Schiff base compounds: Synthesis, structure, and anticancer properties

Sharma

Agnihotri

Kumar

et al. 2021

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

“…Because heteroditopic ligands can facilitate the generation of heterodimetallic assemblies [12,13] and reduce occurrences related to structural diversification, the development of such ligands is being explored in metal coordination chemistry. [14][15][16][17][18][19][20][21] Salicylaldehyde, 2-aminophenol, and 2-aminobenzoic acid are common organic reagents and can be easily converted into Schiff bases by reactions with amines and aldehydes or ketones, respectively (Figure 1a). [22][23][24][25][26][27] The resulting potentially bidentate ligands are ideal for coordination with a large number of metal ions and complexes.…”

Section: Introductionmentioning

confidence: 99%

“…[47,48] Moreover, the steric and electronic properties of the tin atoms are easily modified by variation of the organic substituents. [18][19][20][21][28][29][30]49] To explore the influence of the Sn-R groups on self-assembly products, the organotin fragments employed typically carry methyl, n-butyl, or phenyl groups.…”

Section: Introductionmentioning

confidence: 99%

Triorganotin(IV) derivatives with semirigid heteroditopic hydroxo‐carboxylato ligands: Synthesis, characterization, and cytotoxic properties

Baul

Addepalli

Duthie

et al. 2020

Applied Organom Chemis

Self Cite

View full text Add to dashboard Cite

Three organic hydroxy‐carboxylic acids separated by a semirigid aromatic diaza scaffold and carrying alkyl groups of different steric hindrance (H′HL1, cyclopropyl; H′HL2, cyclohexyl; H′HL3, adamantyl) were employed as pro‐ligands. Their reaction with suitable triorganotin precursors leads to 10 complexes of compositions: [Me3Sn(HL1)]n·0.5nC6H5CH3 1, [Et3Sn(HL1)]n 2, [nBu3Sn(HL1)]n 3, [Ph3Sn(HL1)]n 4, [Me3Sn(HL2)]2·2CH2Cl2 5, [Et3Sn(HL2)]2 6, {[nBu3Sn(HL2)][nBu3Sn(HL2)(H2O)]} 7, [Ph3Sn(HL2)]n·nC2H5OH 8, [nBu3Sn(HL3)]n 9, and [Ph3Sn(HL3)]n 10. The solid‐state structures of 1–10 were deduced from single‐crystal X‐ray diffraction studies along with two of the pro‐ligands: H′HL1 and H′HL2. In the solid state, four different extended structure types were observed. In compounds 1–3 with aliphatic substituents at the tin atoms and a small substituent at the ligand backbone (cyclopropyl), 1D coordination polymers based on carboxylate bridging were observed, whereas compounds 4 and 8–10 with large substituents attached to the metal and the ligand (cyclohexyl and adamantyl) were 1D coordination polymers based on heteroditopic binding of the ligands. Albeit having essentially the same ligand conformation, the compounds having smaller substituents at the tin atoms (5, R = Me; 6, R = Et) comprise 24‐membered macrocyclic ring structures. In 7, water molecules are coordinated to half the tin atoms, giving dinuclear fragments {[HL2][nBu3Sn][HL2][nBu3Sn(H2O)]}, which are linked through OwH···Osal hydrogen bonds into 1D hydrogen‐bonded tapes. In solution, the tin atoms in 1–10 are coordinated to a single monoanionic [HL1–3]− ligand molecule utilizing anisobidentate coordination with the carboxylate group, as revealed from 119Sn nuclear magnetic resonance spectral results. The antiproliferative activity of the tri‐n‐butyl and triphenyltin compounds 3, 4, and 7–10 was evaluated against the cervical cancer cells (HeLa) and normal kidney cells (HEK) using the 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide assay. Of these, the adamantyl‐substituted tin complexes 9 and 10 present increased activity with IC50 values of 0.51 ± 0.01 and 0.41 ± 0.03 (μM) and good selectivity. The cell death mechanism was identified as apoptosis based on dual staining with fluorescent dyes (Hoechst 33342/propidium iodide and acridine orange/ethidium bromide) and might be related to reactive oxygen species.

show abstract

“…Consequently, a variety of structurally characterized motifs based on diorganotin(IV) complexes of amino acetate Schiff bases were categorized viz., [R 2 Sn(L)] (I), [R 2 Sn(L)(solv)] (II), [R 2 Sn(L)] 2 (III), [R 2 Sn(L)SnR 2 ] (IV), [R 2 Sn(L)(solv)] 2 (V), [R 2 Sn(L)] 3 (VI), and [R 2 Sn(L)] n (VII), where R = alkyl or aryl, L = variously substituted Schiff bases derived from α-amino acids and solv = donor solvent. [14] Coordination modes in these complexes can vary from five to seven, thus providing access to a large variety of structural entities. Accordingly, these complexes demonstrated obvious exciting progress in various fields, such as cytotoxicity and antibacterial activity, [15][16][17][18][19][20] photophysical properties useful for NLO applications, [21] fluorescent staining of silk fibroin, [19] and sensing [22] as well as the detection of warfare agents (organophosphate based chemical weapons).…”

Section: Introductionmentioning

confidence: 99%

Diorganotin Compounds Containing α‐Aminoacidato Schiff Base Ligands Derived from Functionalized 2‐Hydroxy‐5‐(aryldiazenyl)benzaldehyde. Syntheses, Structures and Sensing of Hydrogen Sulfide

et al. 2020

Self Cite

View full text Add to dashboard Cite

Three novel bicycloazastannoxides, namely, [nBu 2 Sn(L 1 )] (1), [nBu 2 Sn(L 2 )] (2) and [Bz 2 Sn(L 3 )] (3) were synthesized in one pot procedures by reacting diorganotin(IV) precursors with a mixture composed of an α-amino acid with either (E)-2-hydroxy-5-((4-nitrophenyl)diazenyl)benzaldehyde or (E)-2hydroxy-5-(phenyldiazenyl)benzaldehyde. Single-crystal X-ray diffraction analysis reveal that compound 1 is monomeric, compound 2 consists of both a monomer and a dimer, while compound 3 is a coordination polymer for which two modifications 3A and 3B were identified. The 119 Sn NMR chemical shifts [a] Prof.

show abstract

Molecular aggregations of bicyclodioxazastannone produced from multicomponent reactions involving functionalized 2-hydroxybenzaldehydes, α- or β-amino acids and a dimethyltin precursor

Cited by 10 publications

References 81 publications

Glutamine conjugated organotin(IV) Schiff base compounds: Synthesis, structure, and anticancer properties

Glutamine conjugated organotin(IV) Schiff base compounds: Synthesis, structure, and anticancer properties

Triorganotin(IV) derivatives with semirigid heteroditopic hydroxo‐carboxylato ligands: Synthesis, characterization, and cytotoxic properties

Diorganotin Compounds Containing α‐Aminoacidato Schiff Base Ligands Derived from Functionalized 2‐Hydroxy‐5‐(aryldiazenyl)benzaldehyde. Syntheses, Structures and Sensing of Hydrogen Sulfide

Contact Info

Product

Resources

About