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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]

In this research, a series of N‐phenylsulfonamide derivatives (1‐12) were designed, synthesized, and investigated for their inhibitory potencies against carbonic anhydrase isoenzymes I, II, and IX (hCA I, hCA II, and hCA IX) and cholinesterases (ChE), namely, acetylcholinesterase and butyrylcholinesterase. These compounds, whose inhibition potentials were evaluated for the first time, were characterized by spectroscopic techniques (1H‐ and 13C‐NMR and FT‐IR). CA isoenzyme inhibitors are significant therapeutic targets, especially owing to their preventive/activation potential in the therapy processes of some diseases such as cancer, osteoporosis, and glaucoma. On the other hand, Cholinesterase inhibitors are valuable molecules with biological importance that can be employed in the therapy process of Alzheimer's patients. The results showed that the tested molecules had enzyme inhibition activities ranging from 9.7 to 93.7 nM against these five metabolic enzymes. Among the tested molecules, the methoxy and the hydroxyl group‐containing compounds 10, 11, and 12 exhibited more enzyme inhibition activities when compared to standard compounds acetazolamide, sulfapyridine, and sulfadiazine for CA isoenzymes and neostigmine for ChE, respectively. Of these three molecules, compound 12, which had a hydroxyl group in the para position in the aromatic ring, was determined to be the most active molecule against all enzymes. In silico work, molecular docking has also shown similar results and is consistent with the experimental data in the study. As a result, we can say that some of the tested molecules might be used as promising inhibitor candidates for further studies on this topic. [ABSTRACT FROM AUTHOR]

• Novel heterocyclic Schiff base derivatives bearing aryl sulfonate moiety were synthesized and characterized. • Compounds 13–15 showed noteworthy cytotoxic effect on colon cancer cell line. • Compounds 8 and 17 exhibited significantly cytotoxic influence on liver cell line. • Compounds 8, 13–15 and 17 found to have more toxic effect on liver and colon cell lines than cisplatin. • Compounds (1–18) were docked against target proteins (PDB ID: 5ETY and 6V9C) representing DLD-1 and HepG2 cell lines. In this research, some novel Schiff base derivatives 10–18 were synthesized for the first time, characterized, and tested for their anticancer activities. Spectroscopic characterization of the synthesized molecules 1–18 was carried out by using elemental analysis (C, H, N, S), FT-IR, HRMS, 1H- and 13C- NMR and DEPT-135 spectroscopic techniques. The antiproliferative activity studies of all newly synthesized compounds were tested against different human cancer cell lines, including colon and liver, using an MTT assay for 48 h. Under specified experimental conditions, three molecules (13-15) demonstrated higher cytotoxic activity than other molecules (1-12, 16-18) toward human epithelial colon colorectal cancer cell line (DLD-1) with IC 50 values of 67.88, 56.53, and 48.70 μM, respectively. Besides, two different molecules (8 and 17) were found to have more toxic effects than molecules (1-7, 9-16, 18) against human liver epithelial hepatocellular carcinoma cell line (HepG2) with IC 50 values of 65.72 and 54.84 μM, respectively. The selectivity of these compounds, which show high activity, was also tested on a healthy human cell line (Wl-38). Compounds (1–18) were docked against target proteins (PDB ID: 5ETY and 6V9C) representing DLD-1 and HepG2 cell lines. [Display omitted]. [ABSTRACT FROM AUTHOR]

• Two novel hydrazone derivatives were designed and synthesized. • A detailed theoretical investigation about the chemical reactivities was presented. • Molecular docking calculations support the idea of which the molecules can exhibit anticancer performance. • Calculations made and experimental procedures in this paper will be useful for the synthesis of novel hydrazone derivatives in the future studies. In this research, two new hydrazone derivatives; namely compound 1 (N' -(4-((2-hydroxyethyl)(methyl)amino) benzylidene)nicotinohydrazide) and compound 2 (N '-(4-((2-hydroxyethyl)(methyl)amino) benzylidene)isonicotinohydrazide), were designed, successfully synthesized with high purity by treatment of N -methyl- N -(2-hydroxyethyl)-4-aminobenzaldehyde with nicotinic hydrazide and isoniazid, respectively. Spectroscopic characterization of the synthesized compounds was carried out by using FT-IR, UV–Vis, HRMS, 1H- and 13C- NMR spectroscopic techniques, and elemental analysis (C, H, N). For the synthesized compounds, important quantum chemical parameters like frontier orbital energies, hardness, softness, chemical potential, back-donation energy, first electrophilicity index, second electrophilicity index, electrodonating power, electroaccepting power were calculated and the relations with the chemical stability of these parameters were discussed as detailed. Additionally, anticancer properties of the mentioned compounds were analyzed with the help of Molecular Docking studies. [Display omitted] [ABSTRACT FROM AUTHOR]