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.
The
present study explores the solvothermal synthesis of the Sn-Na
MOF composed of stannatranone cages interconnected through Na bridges.
The MOF was used as a catalytic support to hold palladium nanoparticles.
The nanopalladium-decorated Sn-Na MOF (Pd NPs/Sn-Na MOF) was characterized
by FTIR, PXRD, SEM, TEM, NH3-TPD, and XPS analysis. The
resulting composite Pd NPs/Sn-Na MOF demonstrated catalytic activity
for the conversion of fructose to 5-hydroxymethylfurfural (5-HMF),
which is a promising material for the production of various value-added
chemicals. The catalyst shows rapid conversion (in 3 h), recyclability
(up to 5 cycles), and a high yield of 5-HMF (92.4%) in an aqueous
medium without the formation of the side product levullinic acid.
Further, the successful conversion of stale and rotten apples to 5-HMF
using the developed protocol justifies the scope to convert agrowaste
sugars to value-added products with appreciable yield.
This perspective summarizes various synthetic routes of stannatranes and pseudostannatranes along with their interesting features, such as appearance of satellites in their NMR spectra, cluster formation upon hydrolysis and exchange reactions.
The
synthetic protocols, structural aspects, and spectroscopic
aspects of mononuclear pseudostannatranes possessing a [4.4.3.01,5]tridecane cage have been reported. A tripodal ligand N(CH2CH2OH){CH2(2-t-Bu-4-Me-C6H2OH)}2 (H3L) having unsymmetrical
arms was reacted with n-butyltrichlorostannane, phenyltrichlorostannane,
and tin tetrachloride under different solvent systems to obtain pseudostannatranes
(1–3). The reaction of n-butyltrichlorostannane and the ligand in CH3OH/Na/THF
yielded an aqua complex of pseudostannatrane [LSnBu(H2O)]
(1
a
), which was crystallized
as its acetone solvate (i.e 1
a
·Me2CO). However, the same reactants yielded methanol
complex [LSnBu(CH3OH)] (1
b
) when the reaction was carried out in the NaOCH3/C2H5OH system. Similarly, the reaction of
phenyltrichlorostannane and the ligand under these solvent systems
yielded pseudostannatranes, i.e., an aqua complex [LSnPh(H2O)] (2
a
) and a methanol complex
[LSnPh(CH3OH)] (2
b
) (where 2a
was crystallized as 2
a
·Me2CO). The reaction of
tin tetrachloride and the ligand in the Et3N/THF system
resulted in the formation of pseudostannatrane [LHSnCl2] (3). A similar product was isolated as its triethylamine
solvate (3·NEt
3
) due to the disproportion reaction when PhSnCl3 was reacted
with the ligand in the Et3N/C6H5CH3 system, which demonstrates the first report on the reverse
Kocheshkov reaction in pseudostannatranes. The experimental findings
on the formation of 3·NEt
3
due to the reverse Kocheshkov reaction have been corroborated
with 119Sn NMR spectroscopy and density functional calculations
that provide insightful information about the underlying details of
the reaction route.
A maiden two‐dimensional atrane‐based heterobimetallic MOF (2) was constructed employing a novel tripodal ligand N{CH2COOH}2{CH2(2‐t‐Bu‐4‐CH3‐C6H2‐OH)} (1). Single‐crystal X‐ray diffraction depicted the formation of [4.3.3.01,5] pseudoatrane cage in which copper(II) ions attained trigonal bipyramidal geometry. Besides, the co‐existing sodium(I) ions acquired a pentagonal bipyramidal geometry produced by methanol molecules and free carboxylate sites of the ligand. This compound is the first of its kind where the sequential binding of copper(II) pseudoatrane cage and hepta‐coordinated sodium ion generated a heterobimetallic metal–organic framework with a sheet‐like structure. The TEM and SEM images of the MOF having stability up to 250°C revealed the formation of spherical structures (~78 nm) with flower‐like morphology. The heterobimetallic 2D‐MOF was proved to be a multifunctional material as it successfully catalysed Friedel–Craft's alkylation of Indole with beta‐nitrostyrene as well as utilised for the efficient detection of toxic brominated flame retardants through spectrophotometric and colorimetric studies. Remarkably, the best catalysis results were seen using DCM as a solvent, and the alkylation product obtained from the reaction of 2‐methylindole with 2‐Br‐β‐nitrostyrene showed an extraordinary yield of 98%. Besides, the 2D‐MOF showed a selective response with pentabromophenol, and tetrabromophthalic anhydride with quenching in peak on the addition of TBPA while shifting of the peak was observed from 457 to 402 nm with PBP. The practical application of the MOF was explored by its successful incorporation into portable silica strips for on‐the‐spot detection of BFRs.
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