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In this paper, we present the synthesis and characterization of two known sulfonyl hydrazides (1 and 2) and their new sulfonyl hydrazone derivatives (9–20), as well as in vitro and in silico investigations of their cytotoxic properties against human lung (A549) and human breast (MCF-7) cancer cell lines. The target compounds (9–20) obtained in high yields were synthesized for the first time by a multi-step reaction, and their structures were confirmed by elemental analysis and various spectral techniques, including FT-IR, 1H-, and 13C-NMR. The antiproliferative profiles of these compounds (1, 2, and 9–20) in this study were determined at concentrations of 200, 100, 50, and 25 µM against selected cancer cell lines for 72 h using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) method. Except for compounds 1 and 2, other compounds (9–20) demonstrated cytotoxic activity at concentrations lower than 200 µM. The newly synthesized compounds (9–20) demonstrated antiproliferative activities at a micromolar level, with IC50 values in the range of 29.59–176.70 μM for the A549 cell line and 27.70–170.30 μM for the MCF-7 cell line. Among these compounds, compound 15 (IC50 = 29.59 μM against A549 cell line and IC50 = 27.70 μM against MCF-7 cell line) showed the highest cytotoxic activity against these two cancer cell lines compared to the reference drug cisplatin (IC50 = 22.42 μM against A549 cell line and IC50 = 18.01 μM against MCF-7 cell line). From docking simulations, to establish a plausible binding mode of compounds, we noticed that compound 15 demonstrated the highest affinity (−6.8508 kcal/mol) for estrogen receptor-beta (ERbeta) compared to others, suggesting promising ERbeta binding potential. Most compounds followed Lipinski's rule of five, with acceptable logP values. Additionally, all had mixed gastrointestinal absorption and limited blood–brain barrier permeability. Overall, our study proposed new sulfonyl hydrazones as a potential class of anticancer agents. [ABSTRACT FROM AUTHOR]

The intercalation of pyrazolone-based oxalamide metal complexes into Na-montmorillonite (Na-MMT) for catalytic liquidphase oxidation of phenol using H2O2 was undertaken by a flexible ligand method using metal ions including Mn(II), Zn(II), and Sn(II). First, the metal ions were exchanged with the sodium ions of Na-MMT, and then these metal ions were complexed with a new pyrazolone-based oxalamide ligand. The intercalated metal complexes were characterized by Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy, elemental analysis, and thermogravimetric analysis. Phenol was successfully oxidized by heterogeneous catalysts based on Mn(II), Zn(II), and Sn(II) pyrazolone-based oxalamide complexes intercalated into Na-MMT. These heterogeneous catalysts catalyze the liquid-phase oxidation of phenol using H2O2 to catechol as the major product and hydroquinone and benzoquinone as the minor products. The Mn(II) and Zn(II) complexes intercalated into Na-MMT showed better activity than the Sn(II) complex intercalated into Na-MMT and the reaction without the catalyst. It has been shown that some metal ion complexes intercalated into Na-MMT are active catalysts for liquid-phase oxidation of phenol with hydrogen peroxide. [ABSTRACT FROM AUTHOR]

The intercalation of pyrazolone-based oxalamide metal complexes into Na-montmorillonite (Na-MMT) for catalytic liquidphase oxidation of phenol using H2O2 was undertaken by a flexible ligand method using metal ions including Mn(II), Zn(II), and Sn(II). First, the metal ions were exchanged with the sodium ions of Na-MMT, and then these metal ions were complexed with a new pyrazolone-based oxalamide ligand. The intercalated metal complexes were characterized by Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy, elemental analysis, and thermogravimetric analysis. Phenol was successfully oxidized by heterogeneous catalysts based on Mn(II), Zn(II), and Sn(II) pyrazolone-based oxalamide complexes intercalated into Na-MMT. These heterogeneous catalysts catalyze the liquid-phase oxidation of phenol using H2O2 to catechol as the major product and hydroquinone and benzoquinone as the minor products. The Mn(II) and Zn(II) complexes intercalated into Na-MMT showed better activity than the Sn(II) complex intercalated into Na-MMT and the reaction without the catalyst. It has been shown that some metal ion complexes intercalated into Na-MMT are active catalysts for liquid-phase oxidation of phenol with hydrogen peroxide. [ABSTRACT FROM AUTHOR]

In this research, two new series of N‐arylsulfonyl hydrazone compounds (14–25) possessing a sulfonate moiety were synthesized and characterized by elemental analysis and various spectroscopic techniques including fourier transform infrared (FT‐IR), 1H‐, and 13C nuclear magnetic resonance (NMR). These compounds synthesized as target molecules (14–25) were tested for their in vitro acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition activities and antioxidant potential. The antioxidant capacities of the tested molecules were determined by four different assays. The IC50 values of the screened molecules were determined in the range of 60.14 ± 0.25–84.81 ± 1.09 μM against AChE and in the range of 70.11 ± 0.67–93.60 ± 0.47 μM against BChE. In the AChE assay, 4‐hydroxybenzaldehyde‐based compound 25 (60.14 ± 0.25 μM) showed the highest activity in comparison to rivastigmine (501 ± 3.08 μM). This compound (71.42 ± 0.19 μM) is also one of the compounds with the highest activity against BChE. In the BChE assay, 2‐hydroxybenzaldehyde‐based compound 19 (70.11 ± 0.67 μM) indicated the highest activity in comparison to rivastigmine (19.95 ± 0.20 μM). In antioxidant activity studies, the tested molecules showed lower activities than the standard compounds (butylated hydroxytoluene and α‐tocopherol). Consequently, some novel compounds can be used as potential inhibitor candidates in future studies. [ABSTRACT FROM AUTHOR]

In this study, new mixed ligand Cu(II), Ni(II) and Pd(II) metal complexes were synthesized and characterized by NMR (for ligand), UV‐Vis, elemental analysis, FT‐IR, molar conductivity techniques. While the octahedral structure is recommended for Cu(II) and Ni(II) complexes, the square plane structure is recommended for the Pd(II) complex. The compounds lack conductivity traits indicating their non‐electrolyte nature in solution. Photoluminescence properties of the synthesized mixed ligand complexes were investigated. These three complexes showed emission bands when excited at their maximum absorbances. The excitation/emission bands of the Pd(II) complex shifted to higher (red) wavelengths when compared to the Cu(II) and Ni(II) complexes. The Pd(II) complex showed the Stokes shift of 26 nm. These metal complexes were screened for their anticancer activities against the colon cancer (DLD‐1) and lung cancer (A549) cell lines. The results show that these complexes have antiproliferative activity. In particular, two of the complexes (Pd(II) and Cu(II)) were found to have a higher cytotoxic effect than the positive control drug cisplatin with low IC50 values. [ABSTRACT FROM AUTHOR]

Hypoxia-inducible factors (HIF) are among the targeted treatment strategies with increasing promise in lung cancer, and are known to play a role in tumour growth and other oncogenic properties in cancer cells. Therefore, there is an urgent need for selective HIF inhibitors that can provide therapeutic benefits against lung cancer. In this study, thirty-four chiral compounds designed by combining benzoxadiazole and sulfonamide moieties on the skeleton of the same molecule have been synthesized in S and R enantiomeric forms. In vitro cytotoxic activity and apoptotic effects of the compounds (1a–17a, 1b–17b) have been evaluated using A549 lung cancer cell line and the compounds that induced apoptosis in A549 cells and reduced mRNA expression levels of HIF-targeted genes have been evaluated. Consequently, four molecules with high potential have been developed as target compounds (4b, 6a, 6b and 7a), and the pharmacokinetic properties of these molecules have been determined theoretically. Also, emerging computational methods such as molecular docking, which are conducted to estimate the modes of the interactions of the compounds with HIF-1β, calculations of binding energy and ADMET analysis, have been applied to support the results of in vitro cytotoxic activity. Taken together with all the results, compound 6a with the R configuration seems to be a promising HIF-1β inhibitor candidate for targeted therapy. [ABSTRACT FROM AUTHOR]

In this research work, a series of heterocyclic Schiff base compounds bearing arylsulfonyl ester moiety (2a-i) were designed, synthesized, characterized by spectral techniques such as 1D NMR (¹H and 13C), 2D NMR (COSY and HMQC), and FT-IR; and then examined their antioxidant activity was by using four different methods as DPPH, ABTS, CUPRAC, and β-carotenelinoleic acid assays. According to the results obtained, it determined that all synthesized molecules had antioxidant activity. In the DPPH assay, it was found that compound 2e (IC50: 96.23±0.02 μM/mL) demonstrated the antioxidant activity among all synthesized molecules. In ABTS assay, compounds 2e (IC50: 41.88±0.21 μM/mL) and 2g (IC50: 50.75±0.32 μM/mL) were determined to be the molecules with the activity, respectively. Compound 2e (IC50:73.49±0.00 μM/mL) indicated the best antioxidant activity in the CUPRAC assay compared to other synthesize molecules. In the β-carotene-linoleic acid assay, compound 2e (IC50: 58.79±0.58 μM/mL) displayed antioxidant activity than all other synthesized molecules. Compounds 2d (IC50: 74.17±0.22 μM/mL) and 2g (IC50: 66.06±0.13 μM/mL) indicated higher antioxidant activity than the remaining molecules in this series, except for compound 2e. In conclusion, it is thought that this study will contribute to the ongoing studies on the design and synthesis of new antioxidant agents. [ABSTRACT FROM AUTHOR]

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