Search

The document is the contents list for the journal "Chemical Communications" published in 2024. It includes various articles on topics such as precision photodynamic therapy, materials design for polymers, efficient electrocatalysts, and molecular perovskites. The journal is published by The Royal Society of Chemistry, a leading chemistry community. The document provides a comprehensive overview of the articles included in the journal issue. [Extracted from the article]

Objective: The aim of this study is to produce novel of the new functionally substituted nicotinohydrazones, analyze their anti-inflammatory activity, and assess their toxicity. A promising avenue for the advancement of novel bioactive compounds is the pursuit of "hybrid molecules" that contain pharmacophore fragments within their structural composition, with a particular focus on the examination of these molecules for the discovery of novel biological activities. Methods: The synthesis of nicotinic acid hydrazones (II–VI) was performed by condensation of nicotinic acid hydrazide with various aldehydes in ethanol when refluxing the reaction mixture at 60–70°C. The anti-inflammatory activity was studied using the formalin paw edema method in non-linear white rats. The acute inflammatory reaction was reproduced by subplantar (i.e., underplantar or plantar aponeurosis) injection of 0.1 mL of a 2% formalin solution into the right paw using a conventional insulin syringe. Results and Discussion: The structure of the new functionally substituted nicotinohydrazones has been confirmed by a combination of the 1H and 13C NMR methods, and COSY (1H-1H), HMQC (1H–13C), and HMBC (1H–13C) two-dimensional NMR spectroscopy methods.1H, and 13C NMR spectroscopy were used to investigate all the prepared derivatives. The acute toxicity of the aforementioned compounds was preliminarily evaluated using a specially developed Toxicity Assessment Software Tool within the United States Environmental Protection Agency. The LD50 values for rats following oral administration of the compounds tested by the QSAR method. According to the projected toxicological effects, compounds (II), (III) can be classified into Class 4 in terms of toxicity. Compounds (IV), (V) and (VI) have low toxicity and very low toxicity, respectively. Conclusions: The anti-inflammatory activity of the synthesized hydrazones has been evaluated and it has been demonstrated that these compounds were ineffective in comparison with ibuprofen at a dosage of 100 mg/kg (p2 < 0.05). The low toxicity level of all the tested compounds was predicted by the computer modeling. The LD50 values of the compounds range from 445.461 to 1491.991 mg/kg. The studies on the model of formalin paw edema in nonlinear white rats indicate the absence of an anti-inflammatory effect of the tested compounds. [ABSTRACT FROM AUTHOR]

AbstractAn aroylhydrazone compound (HL) was prepared and explored as a ligand (HL = N’-(2-hydroxy-4-methoxybenzylidene)-3-hydroxy-4-methoxybenzohydrazide). Reaction of the aroylhydrazone ligand with copper bromide and copper chloride afforded two new copper(II) complexes, [Cu2Br2L2] (1) and [CuL(DMF)]Cl (2), respectively. The aroylhydrazone ligand and copper complexes were characterized by CHN elemental analyses and infrared spectroscopy. Structures were further confirmed by single crystal X-ray diffraction experiments. The aroylhydrazone compound coordinates to Cu atoms through its phenolate oxygen, imino nitrogen and carbonyl oxygen. The Cu atom in 1 adopts a square pyramidal coordination, with three donor atoms of one L and one phenolate oxygen of a second L in the basal plane, and with one Br ligand at the apical position. The Cu atom in 2 is square pyramidal, with three donor atoms of one L and one oxygen of a DMF ligand in the basal plane, and with one Cl ligand at the apical position. Crystal structures of the aroylhydrazone and the copper complexes are stabilized by hydrogen bonds. The complexes possess antibacterial activities against B. subtilis, S. aureus and E. coli. [ABSTRACT FROM AUTHOR]

Hydrazone‐type Schiff bases have been widely explored owing to their therapeutic properties. These compounds are known to have antibacterial, antifungal, anticancer, and antioxidant properties, among others. In the present study, six hydrazone‐based Schiff bases (BB1–BB6) were synthesized by the reaction between derivatives of benzaldehyde and benzo hydrazide in methanolic medium in the presence of catalytic amount of formic acid. The synthesized compounds were characterized using various spectroscopic techniques such as NMR (1H, 13C, COSY, DEPT, HSQC, HMBC, and NOESY), FTIR, UV‐Vis, elemental (CHN) analysis, and high‐resolution mass spectroscopy. In addition, single crystal structures of BB2, BB4, and BB6 were obtained. In vitro antidiabetic and antioxidant potential of the compounds was evaluated on glucosidase, amylase, NO, FRAP, and DPPH assays, respectively. In all the assays, compounds BB6, BB4, and BB2 showed higher activity than the others. To further explore the chemical reactivity properties and their mechanism of action against the tested assays, DFT and molecular docking study were performed, and the results obtained reinforce the experimental study data. [ABSTRACT FROM AUTHOR]

Organic semiconducting wires have captured broad attention in recent years due to its tremendous applications in various fields. The structural and chemical versatility, easy fabrication, tunable properties, and low cost have made their inevitable presence in electronics and optoelectronics. Herein, the synthesis and characteristic description of a new thiazolo[3,2‐a] hydrazone‐based organic semiconducting microwire synthesized by the Lewis acid‐based condensation reaction between methyl (Z)‐2‐(2‐(2‐methoxy‐2‐oxoethylidene)‐3‐oxo‐2,3‐dihydrothiazolo[3,2‐a]indol‐9‐yl)‐2‐oxoacetate and phenyl hydrazine under reflux conditions is reported. The optical, electrical, and semiconducting nature of the material is revealed from the specular reflectance study. When the Tauc plot analysis reveals a direct bandgap of 2.03 eV, the hot probe test suggests the nature of the majority of charge carriers as electrons, indicating the hydrazone as an organic semiconductor. The long wire‐like morphology with a high aspect ratio makes the molecule conceivable for advanced optoelectronic applications. [ABSTRACT FROM AUTHOR]

This computational study explores the copper (I) chloride catalyzed synthesis of (E)‐1‐(2,2‐dichloro‐1‐phenylvinyl)‐2‐phenyldiazene (2Cl‐VD) from readily available hydrazone derivative and carbon tetrachloride (CCl4). 2Cl‐VD has been extensively utilized to synthesize variety of heterocyclic organic compounds in mild conditions. The present computational investigations primarily focus on understanding the role of copper (I) and N1,N1,N2,N2‐tetramethylethane‐1,2‐diamine (TMEDA) in this reaction, TMEDA often being considered a proton scavenger by experimentalists. Considering TMEDA as a ligand significantly alters the energy barrier. In fact, it is only 8.3 kcal/mol higher compared to the ligand‐free (LF) route for the removal of a chlorine atom to form the radical ·CCl3 but the following steps are almost barrierless. This intermediate then participates in attacking the electrophilic carbon in the hydrazone. Crucially, the study reveals that the overall potential energy surface is thermodynamically favorable, and the theoretical turnover frequency (TOF) value is higher in the case of Cu(I)‐TMEDA complex catalyzed pathway. [ABSTRACT FROM AUTHOR]

Pinostrobin, an isolated compound from Boesenbergia rotunda, has been shown to have potent anti‐proliferation and apoptosis effects in cancer stem‐like cells. However, its hydrophobic properties reduce its bioavailability. Eight new alkyl‐TPP+ pinostrobin derivatives were synthesized and assessed for their cytotoxicity against the human HepG2 liver cancer cell line using the alamarBlue assay. All derivatives exhibited moderate cytotoxicity, with the IC50 values ranging from 38.55–101.95 μM, and were more potent than pinostrobin and pinostrobin hydrazone (IC50>100 μM). Four alkyl‐TPP+ pinostrobin hydrazone amide derivatives showed more potent cytotoxicity than four alkyl‐TPP+ pinostrobin ester derivatives. QSAR analysis showed key 3D structural descriptors of TPP+‐based compounds responsible for cytotoxicity against HepG2 cells for the first time. The resultant 3D‐QSAR models using PLS and PCR methods were evaluated and found reliable in predicting the cytotoxicity of other TPP+‐based compounds. [ABSTRACT FROM AUTHOR]

In search for new molecules of diterpene origin with promising anticancer activity, two amino‐derivatives (methyl maleopimarate aminoimide and methyl 1β,13‐epoxydihydroquinopimarate C4‐hydrazone) were involved in the 4‐component Ugi reaction (Ugi‐4CR) and pseudo‐7‐component azido‐Ugi condensation (azido‐Ugi‐7CR) to afford a series of adducts holding α‐aminoacylamide and bis‐1,5‐disubstituted tetrazole substituents. The NCI‐60 cancer cell panel screening revealed diterpene‐type Ugi adducts 2, 5, and 6 with strong antiproliferative potency with GI50 in range of 1.2–15.4 μM. The high positive correlations with standard anticancer drugs suggest microtubules or progesterone and androgen receptors as possible targets of the synthesized compounds. [ABSTRACT FROM AUTHOR]

Investigation into the interactions between drugs and biomolecules can offer a precise understanding of their biological behaviours in vitro and in vivo, providing crucial insights for designing new drugs. Herein, we report the design, synthesis, and characterization of a bicyclic hydrazone derivative, along with its potential as an inhibitor of human neutrophil elastase (HNE), a critical enzyme in the treatment of acute and chronic lung injuries. We present an improved protocol for the synthesis of the compound using N‐amino‐bicyclo[2.2.1]hept‐5‐ene‐2,endo‐3‐endo‐dicarboximide and 4‐(trifluoromethyl)benzaldehyde through a facile, one‐pot, catalyst‐free synthesis in dry ethanol at reflux temperature. Within 12 hours, bicyclic‐hydrazone derivative was obtained with yields of up to 75 % and was characterized using various spectroscopic techniques and computational analyses based on the DFT approach. In silico ADME/T profile of the compound was evaluated and molecular docking simulation was utilized to predict its potential as a HNE inhibitor. The binding energy values of the THI ligand to the chosen PDB ID: 5ABW, 3Q77, and 2RG3 target proteins were determined as −8.41, −7.20, and −7.27 kcal/mol, respectively. In silico analysis findings indicate that the THI compound has promising drug‐likeness properties and has the potential to be evaluated in the development of new HNE inhibitors. [ABSTRACT FROM AUTHOR]

Background and Aims: The pursuit of new antimicrobial agents to address antimicrobial resistance remains a fundamental effort in supporting sustainable global health endeavours. Hydrazone compounds possess numerous advantages as biologically active agents because of their diverse properties. In our work, a series of hydrazone derivatives (4a-f) containing the ibuprofen moiety were synthesised and evaluated as antibacterial and antifungal agents. Methods: Novel hydrazone derivatives were synthesised through the condensation of 2-[4-(2- methylpropyl)phenyl]propanehydrazide with suitable cyclohexanone derivatives. The structure of the new compounds was confirmed using spectral methods such as IR, ¹H-NMR, 13C-NMR (APT) and electrospray ionisation mass spectrometry (ESI-MS). Testing involved six compounds and their standards against a range of bacterial and fungal strains, including Gram-positive and Gram-negative bacteria, as well as Candida spp. MIC values were determined using the microbroth dilution method. Results: Each of the tested molecules exhibited varying inhibitory effects across six distinct targets, resulting in different MIC values. Compounds 4a, 4e, and 4f showed moderate antimicrobial activity compared with the standards. Conclusion: Among the tested compounds, compound 4a demonstrated the most potent antimicrobial activity against the P. mirabilis strain, with an MIC value of 312.5 μg/mL. Further modification and development of ibuprofen-hydrazone derivatives against targets may result in new antimicrobial drug candidates in the near future. [ABSTRACT FROM AUTHOR]

In the twenty-first century, we are witnessed of a large number of infectious ailments which spread very quickly worldwide and effect the public health significantly. Thus, in the current research, with the aim of a suitable malaria and oxidant controlling agent, micro-assay, DPPH and ABTS protocols were conducted against previously synthesized and well-characterized (mass spectrometry, NMR (1H and 13C), powder XRD, IR, electronic spectra, TGA magnetic moment, molar conductivity and SEM) hydrazone ligands (1–2) and their Co(II), Ni(II), Cu(II), Ni(II) metal complexes (3–10) of benzaldehyde derivatives and 3,5-dichlorobenzohydrazide. The biological assessment revealed that the (8), (9), (10) complexes were more potent to inhibit the malarial and oxidant infections although the complex (10) has highest ability (0.42 ± 0.05 µM for antimalaria and 1.98 ± 0.09–99 ± 0.08 µM for antioxidant) to control these diseases with comparable IC50 value to quinine and ascorbic acid. Moreover, molecular docking (against 8E1Z and 1U5A proteins), DFT and ADMET investigations were examined against the highly potent HL2 ligand and its (7–10) complexes to corroborate the acquired biological findings. The theoretical investigations also advocate the more potency of complex (10) through significant binding affinity, binding modes, hardness, softness, etc. [ABSTRACT FROM AUTHOR]

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 an effort to develop new and effective therapeutic agents for Alzheimer's disease, a series of hydrazone derivatives bearing piperidine rings have been designed and synthesized. The chemical structures of the compounds were characterized by various spectroscopic techniques. In vitro antioxidant and cholinesterase activities of the compounds were evaluated. Among the compounds, N12 exhibited the most antioxidant activity in all methods (CUPRAC, FRAP, DPPH, ABTS). In vitro acetylcholinesterase (AChE) activity results of the compounds showed good IC50 values between 14.124 ± 0.084 and 49.680 ± 0.110 µM were obtained (IC50 = 38.842 ± 0.053 µM for Donepezil). Among the compounds, N7 and N6 are much more effective derivatives than the standard compound donepezil with IC50 values of 14.124 ± 0.084 and 17.968 ± 0.072 µM, respectively. In vitro, butyrylcholinesterase (BChE) inhibition values of the compounds were between 13.505 ± 0.025 and 52.230 ± 0.027 μm. Among the compounds, N6 has the highest BChE inhibition with an IC50 value of 13.505 μm in the series. The cytotoxicity and AChE inhibitory activity of the compounds on SH‐SY5Y cell lines were also evaluated. Kinetic studies were also performed to determine the behavior of the compounds as competitive or noncompetitive inhibitors. The binding modes of N6, which was determined to be highly effective according to in vitro analyses, with AChE and BChE were investigated using molecular docking studies, and the stability of the complexes was determined by molecular dynamics simulations. These findings indicated that AChE and BChE enzymes maintained their overall structural stability and compactness during interactions with compound N6. [ABSTRACT FROM AUTHOR]

Based on the provided context, a series of new indole-hydrazone derivatives were synthesized and their structures were determined through elemental and spectral studies. These synthesized compounds were then tested for their anti-inflammatory activity using carrageenan-induced oedema in albino rats, with indomethacin as the standard drug. The synthesized compounds exhibited a reduction in oedema formation ranging from 72.3% to 89.3%, surpassing the inhibition observed with indomethacin (46%). Additionally, the compounds were evaluated for their anticancer activity against the MCF-7 breast cancer cell line at a dose of 100μg/ml. Compounds 2f and 2j demonstrated mild anticancer activity with 61% and 68% inhibition, respectively, compared to doxorubicin. Furthermore, molecular docking studies were conducted using the Molego virtual docker program, which revealed that all prepared compounds exhibited high docking scores against both cox-1 and cox-2. The docking scores and binding energy correlated well with the pharmacological results. Lastly, the drug likeness and bioactivity of the compounds were predicted using Molinspiration software, indicating that all new compounds possess favorable drug likeness and bioactivity scores. [ABSTRACT FROM AUTHOR]

In recent times, there has been a growing exploration of transition metal complexes as potential solutions for significant health challenges, including tuberculosis, microbes infection, and inflammation. Therefore, in our ongoing effort to identify biologically effective agents, Co(II), Ni(II), Cu(II), and Zn(II) metal complexes of H2L1–H2L2 hydrazone ligands were synthesized. The structural features of synthesized compounds were recognized by employing several techniques such as FT‐IR, 1H NMR, 13C NMR, powder x‐ray diffraction (XRD), UV‐Vis, ESR, TG‐DTA, mass spectrometry, and molar conductance measurements. The bonding of ligands via Ophenolic, Oenolic, and Nazomethine donor atoms and the attachment of the three water molecules with metal ion to form the octahedral structure of complexes were corroborated by different spectroscopic techniques. The anti‐tuberculosis, antimicrobial, and anti‐inflammatory activities of the synthesized compounds were assessed using the microplate alamar blue assay, serial dilution, and bovine serum albumin (BSA) methods, respectively, and highlighted the more potency of the complexes than ligands. The synthesized Cu(II) (9) and Zn(II) (10) metal complexes exhibited excellent ability to inhibit the growth of H37Rv strain of Mycobacterium tuberculosis in comparison to standard drug streptomycin. The Cu(II) (6 and 9) and Zn(II) (10) complexes showed superb ability as antimicrobial agents, whereas Cu(II) (5) and Zn(II) (6) complexes exhibited significant anti‐inflammatory ability. The in vitro findings on the antituberculosis activity were reinforced by a significant molecular docking study, which has become a crucial component of computational research utilizing the enzyme Mtb Pks13 thioesterase domain of M. tuberculosis. Additionally, in this research work, the absorption–distribution–metabolism–excretion–toxicity (ADMET) study sparked the compounds' drug‐like behavior. [ABSTRACT FROM AUTHOR]

BACKGROUND: The natural product paeonol is a rich and sustainable natural bioresource, and its derivatives have various unique biological efficacy. As is well known, Schiff bases are a class of organic compounds with a wide range of biological activities, including anti‐fungal, insecticidal, anti‐viral, and nematicidal. RESULTS: To discover biorational natural product‐based pesticides, nine intermediates (2–10), 12 sulfonylhydrazones (11a–11c, 12a–12c, 13a–13c, and 14a–14c) and 20 benzylidene hydrazones (18a–18r, 19a, and 20a) were synthesized by structural modification of paeonol, and their structures were characterized by proton nuclear magnetic resonance (1H NMR), carbon‐13 (13C) NMR, and high‐resolution mass spectrometry (HRMS). The stereochemical configurations of compounds 14a, 18d, and 18r were unambiguously confirmed by single‐crystal X‐ray diffraction. Furthermore, bioactivities of these compounds as anti‐oomycete, anti‐fungal, and nematicidal agents against three serious agricultural pests, Phytophthora capsici, Fusarium graminearum, and Heterodera glycines were evaluated. Among all tested compounds: (i) compound 7 exhibited promising anti‐oomycete against Phytophthora capsici, with a half maximal effective concentration (EC50) value of 15.81 mg L−1; (ii) compounds 2, 7, 10, and 19a displayed promising anti‐fungal against F. graminearum, with EC50 values of 12.22, 14.72, 23.39, and 33.10 mg L−1, respectively; (iii) ten compounds (12a–12c, 14c, 18g–18j, 18m, and 19a) showed significant nematicidal activity against H. glycines, with median lethal concentration (LC50) values all less than 30.00 mg L−1. Especially for compound 18g, its LC50 value is the smallest, at 12.65 mg L−1. CONCLUSION: The research results indicate that introducing nitro groups at the C5 position of paeonol, or introducing halogens at both C5 and C3 positions, can significantly enhance its biological activity against Phytophthora capsici, F. graminearum, and H. glycines. © 2024 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

Hydrazone‐linked covalent organic frameworks (COFs) with structural flexibility, heteroatomic sites, post‐modification ability and high hydrolytic stability have attracted great attention from scientific community. Hydrazone‐linked COFs, as a subclass of Schiff‐base COFs, was firstly reported in 2011 by Yaghi's group and later witnessed prosperous development in various aspects. Their adjustable structures, precise pore channels and plentiful heteroatomic sites of hydrazone‐linked structures possess much potential in diverse applications, for example, adsorption/separation, chemical sensing, catalysis and energy storage, etc. Up to date, the systematic reviews about the reported hydrazone‐linked COFs are still rare. Therefore, in this review, we will summarize their preparation methods, characteristics and related applications, and discuss the opportunity or challenge of hydrazone‐linked COFs. We hope this review could provide new insights about hydrazone‐linked COFs for exploring more appealing functions or applications. [ABSTRACT FROM AUTHOR]

A series of some new 1,3,4‐oxadiazole derivatives was synthesized. Hydrazide derivative 4 was reacted with some sugar aldehydes to give the corresponding sugar hydrazones 5 a–c. Acetylation of 5 a–c with acetic anhydride in pyridine, managed the per‐O‐acetyl derivatives 6 a–c while refluxing in acetic anhydride gave the corresponding 1,3,4‐oxadiazolines 7 a–c. On the other hand, 1,3,4‐oxadiazoles 8 a,b, 9, 10, 12, 14, and 15 were synthesized via the reaction of 4 with different reagents including p‐chlorobenzoic acid, nicotinic acid, methyl iodide, morpholine, phenyl isothiocyanate, potassium iodide, chloroacetyl chloride, and phosphorus oxychloride, respectively. The new compounds were assessed for their anticancer and antioxidant activities. Compounds 8 a,b, 10, and 12–15 displayed the most antioxidant activity. In addition, compounds 8 a, 8 b, and 13 showed strong cytotoxic activity. [ABSTRACT FROM AUTHOR]

This article discusses the synthesis of acyl hydrazides and hydrazones from activated amides, which are nitrogen-containing compounds found in pharmaceutical and agricultural compounds. The traditional method for synthesizing acyl hydrazides has limitations, but recent advancements in carbon-nitrogen bond activation reactions have opened up new possibilities. The article provides a comprehensive account of the results and methodologies for synthesizing these compounds, including the synthesis and characterization of various benzohydrazide compounds. The document also includes specific details for the synthesis and characterization of one compound, (E)-N'-(4-methylbenzylidene)benzohydrazide. The document provides experimental results, including yields, melting points, and spectroscopic data, and acknowledges the Korea Basic Science Institute for providing additional data. [Extracted from the article]

Ten isatin-based hydrazone derivatives were synthesized using two subseries, IA (isatin + acetophenone) and IB (isatin + benzaldehyde), and evaluated for their monoamine oxidases (MAOs) inhibitory activity. All the compounds showed stronger MAO-A inhibition than MAO-B, and the IB series showed more effective MAO-A inhibitory activity than IA series. Compound IB4 most potently inhibited MAO-A (half maximal inhibitory concentration IC50 = 0.015 µM), followed by IB3 (IC50 = 0.019 µM). On the contrary, compound IB3 showed the highest MAO-B inhibition (IC50 = 0.068 µM), followed by IB4 (IC50 = 1.87 µM). Compound IB3 and IB4 had low selectivity indices of 3.68 and 8.50, respectively. Structurally, the methyl group of IA series decreased the inhibition of both MAO-A and MAO-B. Among them, IB3 and IB4 (4-Cl and 4-Br in B-ring, respectively) showed higher MAO-A and MAO-B inhibition than the other substitutions. Inhibition constant Ki values of IB3 and IB4 for MAO-A were 0.0088 and 0.0063 µM, respectively, and those for MAO-B were 0.048 and 0.060 µM, respectively. IB3 and IB4 were competitive, reversible inhibitors of MAO-A and MAO-B. Molecular docking analysis predicted that IB3 and IB4 formed stable hydrogen bonds between Asn181 and the NH atom of isatin in the ligand-protein complex. Dynamic analysis revealed that IB3 and IB4 are stable with both MAO isoforms. These observations suggest IB3 and IB4 are potent and reversible MAO-A and MAO-B inhibitors and both compounds can be used as therapeutic agents for neurological disorders. [ABSTRACT FROM AUTHOR]

Melatonin (N‐acetyl‐5‐methoxytryptamine, MLT) is suggested as a preventive agent and potential therapeutic option for breast cancer via its antioxidant as well as anticancer effects by modulating estrogen dependent and independent pathways. However, its rapid metabolic inactivation led scientists to discover novel MLT analogues. Therefore, a series of new indole‐based hydrazide/hydrazone derivatives were synthesized and characterized as MLT analogues in the present study. The initial aim is to investigate the cytotoxicity of novel 1‐ethyl indole hydrazone derivatives against two human breast cancer cells (MCF‐7 and MDA‐MB‐231) as well as a non‐tumorigenic human breast epithelial cell (MCF‐10A). Selective cytotoxic compounds for cancer cells are further investigated for their effects on selected targets; agonist/antagonist activity on estrogen receptor (ER) and inhibitory effects on aromatase and CYP1B1. Their potential antioxidant activity was also investigated by both cell based and cell free in vitro assays. Possible binding of the compounds to the selected targets is also explored by molecular modelling studies. Nonsubstituted compound E1 inhibited human aromatase and the CYP1B1 enzyme with IC50 values of 0.89 μM and 0.5 μM, respectively. Compounds EI 4 and EI 11 exhibited ER antagonist activity with IC50 values of 2.88 μM and 5.29 μM, respectively. Additionally, both EI 4 and EI 11 inhibited CYP1B1 enzyme within 60–100 nanomolar range. In conclusion among 19 tested derivatives EI 1, EI 4 and EI 11 affected either one or more targets besides their selective cytotoxic effect for MCF‐7 cells suggesting that they can be promising candidates in prevention/treatment of ER‐positive breast cancer. Further studies are needed to elucidate their metabolism, in vivo effects, and safety. [ABSTRACT FROM AUTHOR]

In this article, we used thiophene-2-carboxamides as a starting material to synthesize a novel series of L-phenylalanine-tethered peptide hydrazones 6a–6o in three steps. The Broth Dilution Method was used to test the substance' s antibacterial activity in vitro against a variety of bacteria and fungi. Compounds 6c, 6d, and 6g showed potent antibacterial activity against E. coli (MTCC 443) at 50 µg/mL; compounds 6a, 6b, 6g, and 6l were effective against P. aeruginosa (MTCC 1688); compound 6c was effective against S. aureus (MTCC 96); and compound 6a, 6c, and 6g were effective against S. pyogenes (MTCC 442). 6a, 6b, 6d, 6e, 6f, 6h–6l, 6n, and 6o all show considerable antifungal activity against C. albicans (MTCC 227) at 500 µg/mL. The effectiveness of synthesized compounds in a microbiological study was predicted using an in silico investigation of their pharmacokinetic properties (ADME). [ABSTRACT FROM AUTHOR]

Herein, new thiazole‐2‐yl‐based hydrazone derivatives were synthesized and assessed for in vitro anticancer activity against wild type A549, MCF7, DU145, and mutant H1975 cancer cell lines by 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide (MTT) assay. Among all, 4‐(4‐Chlorophenyl)‐2‐(2‐((4‐methylthiazol‐5‐yl)methylene)hydrazineyl)thiazole (4b) elicited prominent anticancer activity against wild‐type epidermal growth factor receptor (WT‐EGFR) MCF7 cancer cell line with an IC50 value of 9.57 ± 1.80 μM, whereas 4‐Methyl‐5‐((2‐(4‐(4‐nitrophenyl)thiazol‐2‐yl)hydrazineylidene)methyl)thiazole (4c) showed appreciable activity with an IC50 value of 11 ± 0.7 μM against the mutated EGFR H1975 lung cancer cells. Doxorubicin and Osimertinib were used as the standard drugs for comparison of activity. Compound (4b) significantly increased early apoptosis (30.2%) and late apoptosis (7.6%) at a 5 μM concentration in comparison with the control (early apoptosis 2.5%, late apoptosis 1.2%). The molecular docking study was performed against mutant EGFR (T790M/C797S) (PDB: 5D41) enzyme to gain information about interactions of synthesized molecules with binding pockets. Moreover, ADME study and molecular dynamic simulation studies were accomplished to gain insight into drug‐likeness and conformational stability, respectively. The findings demonstrate a promising alignment between the observed anticancer effects and computational analyses. [ABSTRACT FROM AUTHOR]

We systematically investigated the first-order molecular hyperpolarizability, a second-order nonlinear optical phenomenon of 185 organic compounds comprising both benzophenone and benzophenone hydrazone derivatives. We considered compounds with different combinations of electron donor groups -H, -F, -CH3, -Cl, -Br, OCH3, -NH2, -NHCH3, -NHC2H5, -N(CH3)2, and electron acceptor group -NO2 attached to the para positions R1 or R2 of the aromatic rings. The reported first-order molecular hyperpolarizability values were obtained by quantum-chemical calculations using semiempirical and density functional theory approaches in the gas phase. Our results reveal that BP-25 (R1 = NO2, R2 = N(CH3)2) and BPH-39 (R1 = N(CH3)2, R2 = NO2) exhibited the highest dynamic first-order molecular hyperpolarizability value of about . These findings underline the potential of specific BP and BPH derivatives as candidates for photonic applications, particularly for developing second harmonic generation crystals. [ABSTRACT FROM AUTHOR]

In the presence of ethanol solvent and glacial acetic acids, triazole reacted with different aromatic aldehydes such as 4-methoxybenzaldehyde, 4-hydroxybenzaldehyde, and benzaldehyde to form the imines group known as Schiff bases. Triazole Schiff bases are triazole hydrazone and their derivatives, VA, VB, and VC. The structures of these synthetic triazole hydrazone derivatives were characterized by means of FT-IR and mass spectrometry. The purities and quality of the compounds were evaluated using TLC. It was established, that the active ingredient in the synthesised triazole hydrazone was more effective against the infections than cefuroxime. [ABSTRACT FROM AUTHOR]

A novel acylhydrazide‐based gelator (BE) was successfully built without the use of traditional fluorescent groups. Surprisingly, in 1,2‐propanediol, the BE can further self‐assemble into a stable supramolecular gel (OBE) and display significant blue‐white aggregation‐induced enhanced emission (AIEE). Interestingly, based on the excellent coordination capacity of acyl hydrazone bonds, the OBE demonstrated a sensitive response to Pd2+ and Fe3+, with corresponding lowest limits of detection of 21.8 and 37.3 ppb, respectively. More interesting, H2PO4− could only be constantly recognized by the Pd‐OBE (Pd2+ coordinated with OBE). Fourier transform infrared (FT‐IR), scanning electron microscopy (SEM), X‐ray diffraction (XRD), density functional theory (DFT) and rheological measurements, the self‐assembly process of OBE, and the ion recognition sensing mechanism were extensively examined. Moreover, xerogel OBE as supporter, a novel heterogeneous catalyst Pd/OBE is prepared. The catalyst displays outstanding activity and stability for Suzuki coupling reactions in water. It can be easily reused for at least five runs with no decrease in the catalytic activity. [ABSTRACT FROM AUTHOR]

Leishmaniasis is a disease caused by protozoa Leishmania spp., considered as a significant and urgent public health problem mainly in developing countries. In the absence of an effective vaccine, the treatment of infected people is one of the most commonly prophylactic measures used to control this disease. However, the therapeutic arsenal is reduced to a few drugs, with serious side effects and variability in efficacy. Attempting to this problem, in this work, a series of benzothiazole derivatives was synthetized and assayed against promastigotes and intracellular amastigotes of L. amazonensis, as well as the toxicity on macrophages. In addition, studies about the mechanism of action were also performed. Among the synthesized molecules, the substitution at position 4 of the aromatic ring appears to be critical for activity. The best compound exhibited IC50 values of 28.86 and 7.70 μM, against promastigotes and amastigotes of L. amazonensis, respectively, being more active than miltefosine, used as reference drug. The in silico analysis of physicochemical and pharmacokinetic (ADMET) properties of this compound suggested a good profile of oral bioavailability and safety. In conclusion, the strategy of using benzothiazole nucleous in the search for new antileishmanial agents was advantageous and preliminar data provide information about the mechanism of action as well as in silico parameters suggest a good profile for preclinical studies. [ABSTRACT FROM AUTHOR]

Hydrazones display an interesting profile of biological activities, which includes mainly antimicrobial and antiproliferative properties. Hydrazones also play an important role in the synthesis of heterocyclic rings and in coordination chemistry. Currently, the synthesis of complexes of hydrazones with transition metals is quite frequently reported in the scientific literature. The interest in this topic is largely due to diverse biological activities of the metal complexes of hydrazones that in some cases are much more effective than hydrazones themselves. This review focuses on the complexes of hydrazones with transition metals which display antibacterial, antitubercular, antifungal and anticancer activities. In the following subchapters devoted to a given activity, an attempt has been made to present the most active complexes of hydrazones, their trends in their activity and application in medicinal chemistry. The paper presents the literature data from 2009 to 2023. This review constitutes a useful guide for the researchers who intend to synthesize and investigate complexes of hydrazones in terms of their antimicrobial and anticancer activities. [ABSTRACT FROM AUTHOR]

A highly sensitive micelle-induced sensory has been developed for detection of long-chain aldehydes as potential biomarkers of respiratory cancers. The micelle-like sensor was fabricated through the partial self-assembly of CTAB and S2 surfactants, containing a fluorescent hydrazine-functionalized dye (Naph-NH2). In principle, long-chain aldehydes with amphiphilic character act as the induced-fit surfactants to form well-entrapped micellar particles, as well as react with Naph-NH2 to form hydrazone derivatives resulting in fluorescent enhancement. The limit of detection (LOD) of micellar Naph-NH2/CTAB/S2 platform was calculated to be ∼ 64.09–80.98 µM for detection of long-chain aldehydes, which showed fluorescent imaging in lung cancer cells (A549). This micellar sensory probe demonstrated practical applicability for long-chain aldehyde sensing in human blood samples with an accepted percent recovery of ~ 94.02–102.4%. Beyond Naph-NH2/CTAB/S2 sensor, the milcellar hybrid sensor was successfully developed by incorporating a micelle-like platform with supramolecular gel regarding to carboxylate-based gelators (Gel1), which showed a tenfold improvement in sensitivity. Expectedly, the determination of long-chain aldehydes through these sensing platforms holds significant promise for point-of-care cancer diagnosis and therapy. [ABSTRACT FROM AUTHOR]

A new class of benzisoxazole‐Chromene (BC) analogues containing acyl hydrazones BCA (5a‐5m) were obtained by the condensation of different benzo hydrazides with BCs in good yield. All the synthesized BCA analogues were evaluated for their in‐silico activity against Acetylcholine Esterase (AChE). According to docking experiments, the co‐crystallized ligand was outperformed by derivatives 5e (4‐benzisoxazole‐chromene‐3‐(4hydroxyphenyl) acrylohydrazide), 5m (7‐chloro,4‐hydroxy) and 5l (8‐methyl, m‐nitro) showed superior binding modes and binding free energies whereas compound 5j (8‐methyl, 4‐hydroxy) showed appropriate binding energy. These moieties containing acyl hydrazone has shown 4‐fold increase in the binding interactions and orientation. According to ADMET and toxicity studies, derivatives 5e, 5m, 5j, and 5l had the potential to be drugs and have proven to be safe when evaluated using seven toxicity models. Further on checking selectivity with the other cholinesterase enzyme, 5l came out to be selective towards AChE whereas 5e & 5j were acting on another target as well. Finally, DFT analysis validated the binding of the derivatives towards AChE and moreover Molecular Dynamic investigation revealed that 5l is the most capable candidate to interact with the target receptor by comparing its molecular orbital energies, molecular electrostatic potential maps, and ligand movement against the co‐crystallized Ligand. [ABSTRACT FROM AUTHOR]

By the reaction of 5-tert-butyl-2- and -3-furoyl phosphonates with acylmethylenetriphenylphosphoranes a series of 1-R-1-oxo-3-(3-methyl-5-tert-butylfuran-2-yl)- and -R-1-oxo-3-(3-methyl-5-tert-butylfuran-3-yl)-3-(diethoxyphosphoryl)-2-propenes was synthesized. It was shown that depending on R nature and location of alkene fragment in the furan ring in the reactions with hydrazine and its derivatives hydrazones or pyrazolines, the products of consequent addition at the double bond, are formed. Diethyl (Е)-{1-[5-(tert-butyl)-3-(methyl)furan-2-yl]-3-oxobut-1-en-1-yl}phosphonate semicarbazone is oxidized with selenium dioxide to corresponding 1,2,3-selenodiazole. 3-(3-Formyl-5-tert-butylfuran-2-yl)-3- and 3-(2-formyl-5-tert-butylfuran-3-yl)-3-(diethoxyphosphoryl)acrylates are synthesized. When treated with hydrazine hydrate they undergo cyclization to the derivatives of 5,6-dihydro-4Н-furo[2,3-d][1,2]diazepine and 7,8-dihydro-6Н-furo[3,2-d][1,2]diazepine respectively. Diethyl (Е)-{1-[5-(tert-butyl)-2-(sulfanylmethyl)furan-3-yl]-3-oxo-3-phenylprop-1-en-1-yl} phosphonate undergo spontaneous cyclization to the derivative of 5-benzoyl-4,7-dihydro-5Н-thiopyrano[3,4-b]furan, while at the reversed location of substituents nuclephylic addition to the double bond does not proceed. [ABSTRACT FROM AUTHOR]

Objective: The "fall armyworm" also known as Spodoptera frugiperda, is a maize pest that is native to North America. It invaded Africa in 2016 and caused serious economic damage, forcing the continent's nations to take swift action to fend off this new invading pest. It is urgently necessary to produce powerful insecticides for the efficient management of this insect pest since this parasite is a novel invading species and its resistance to insecticides has to be investigated. Methods: The synthesized thiazole-owing hydrazone derivatives are the subject of the first study on the harmful effects they cause, followed by structural relationships. Following the stated protocols, four molecules of thiazole-owing hydrazone derivatives were synthesized as pure active ingredients, and their efficacy as potential insecticides against S. frugiperda was tested. Results and Discussion: The toxicity data exhibited that compound (V) with LC50 of 13.66 and 106.25 ppm was more toxic against the 2nd and 4th larvae instars, respectively, than other synthesized compounds; the other screened compounds showed weak to strong toxicological activity against S. frugiperda. A molecular docking investigation of four synthetic compounds (III–VI) was performed against acetylcholinesterase (AChE). The molecular docking results revealed that compound (V) has the more negative docking score and best binding (docking score = –9.01 kcal/mol), followed by compounds (III), (IV), and (VI) with docking scores of –8.76, –8.53, and –7.41 kcal/mol, respectively. The protein-ligand docking postures revealed that these substances exhibited a strong affinity for the target enzyme's active site (Protein Data Bank ID: 2ACE). This work suggests that these substances may have insecticidal and AChE inhibitory properties, and it may be possible to further explore them in the process of creating pesticides that target AChE. [ABSTRACT FROM AUTHOR]

Objective: A new series of pyrazole-3-carbaldehyde derivatives from new hydrazones by using the Vilsmeier–Haack reaction were synthesized. Pyrazoles have the characteristic qualities of the aromatic system, which are generally quite evident in their structures having insecticide, herbicide, and healthful significance as anti-inflammatory properties and antipyretic medication actions. Pyrazole compounds have a wide spectrum of bioactivity as reported in the literature, which encourages synthesis and testing of the antimicrobial activity for synthesis compounds. Methods: P-acetamido-phenol, and 2-mercaptobenzoimidazole, which used as a starting materials for synthesis pyrazole-3-carbaldehyde derivatives. The biological activity of some prepared compounds was also tested against two G-positive bacteria and two G-negative bacteria, in addition to C. albinos fungi. A molecular modeling study of some prepared compounds showed good binding strength with the target protein. Results and Discussion: Compound N-(4-((5-(4′-(4-formyl-1-phenyl-1H-pyrazole-3-carbonyl)-[1,1′-biphenyl]4-yl)-1,3,4-oxadiazol-2-yl)methoxy) phenyl)acetamide passes a good activity against Staphylococcus aurous; the compound 3-(4′-(5-(((1H-benzo[d]imidazol-2-yl)thio)methyl)-1,3,4-oxadiazol-2-yl)-[1,1′-biphenyl]-4-carbonyl)1-phenyl-1H-pyrazole-4-carbaldehyde passes good active with C. albinos. Molecular modeling was studied for the compounds prepared with human corona virus NL63, compound N-(4-((5-(4′-(4-formyl-1-phenyl-1H-pyrazole-3carbonyl)-[1,1′-biphenyl]-4-yl)-1,3,4-oxadiazol-2-yl)methoxy)phenyl)acetamide has best docking score –181.9 kcal/mol, while compound 3-(4′-(5-(((1H-benzo[d]imidazol-2-yl)thio)methyl)-1,3,4-oxadiazol-2-yl)[1,1′-biphenyl]-4-carbonyl)-1-(4-nitroph enyl)-1H-pyrazole-4-carbaldehyde has best hydrogen-bonding with –10 kcal/mol. In general, the binding by hydrogen bonding and steric interference was high, which leads to the conclusion that the prepared compounds have an effect on the Corona virus. Conclusions: The prepared compounds have biological activity and have good binding force with the Corona virus protein NL63, thus disrupting its work, and ccording to the toxicity assessment, the synthesized compounds belong to the third class (III). [ABSTRACT FROM AUTHOR]

Hydrazones are a large group of compounds with antibacterial, antituberculosis, antifungal, anticonvulsant, antiviral, antiprotozoal, anticancer and anti-inflammatory properties. Ten newly synthesized hydrazones were tested for their antimicrobial and antituberculosis activities. Screening tests were performed using the disk diffusion method. Then, the minimum inhibitory concentration (MIC) and minimum bactericidal concentration were determined for the most promising compounds. Synergy of the action of the tested substances with reference drugs was also tested. Drugs standardly used in the treatment of tuberculosis: rifampicin and isoniazid were used as reference substances. Based on the obtained results, fractional inhibitory concentration coefficients were calculated for individual combinations. The tested ones showed weak antimicrobial activity. They didn't show either synergism of action with rifampicin and isoniazid. Then, experimental and theoretical lipophilicity parameters were determined for the obtained derivatives. The research was carried out using reversed-phase high-performance liquid chromatography (RP-HPLC), in which the mobile phase is a mixture of methanol and water. To confirm the validity of the chromatographic technique used, both experimental and calculated lipophilicity parameters were correlated. The correlation matrix of these relationships was subjected to principal component analysis (PCA). [ABSTRACT FROM AUTHOR]

The coexistence of two fragments, a chiral isosteviol moiety and an achiral pyridinoyl-hydrazone moiety, in the molecules of pyridinoyl-hydrazone derivatives of isosteviol results in the realization of two distinct supramolecular motifs in their crystals, namely, a true homochiral motif and a pseudosymmetric homochiral motif. [ABSTRACT FROM AUTHOR]

In the present study, new series of benzoxazolin-2-one linked to a variety of hydrazones and azoles were synthesized and assessed for their antibacterial properties against different bacterial microorganisms. All the synthesized target compounds were characterized by 1H NMR, 13C NMR and IR spectroscopy, and elemental analysis as well. The antibacterial activity of the synthesized compounds was evaluated according to the bacteriostatic and bactericidal activity against the tested pathogen strains by determining the minimum inhibition (MIC) and minimum bactericidal (MBC) concentrations and MBC/MIC ratios. The MIC was evaluated by the broth dilution and the MBC was evaluated by plating methods. The in vitro analysis suggested that some compounds, namely, amide, 5-chlorobenzimidazole, hydrazones with a 3-chloro substitution on the additional phenyl ring, and hydrazones with 2-furyl and 5-nitro-2-furyl substituents, demonstrated wide antibacterial activity against Escherichia coli, Bacillus subtilis, Staphylococcus aureus, and Salmonella Enteritidis. The most sensitive strains appeared to be Gram-negative E. coli and Gram-positive B. subtilis, while S. aureus showed some resistance. The most resistant pathogen was found to be S. enteritidis. The remaining compounds demonstrated moderate to low antibacterial potential. The research results have shown that benzoxazolinone-based derivatives are suitable for the development of a library of compounds and can be used in the future development of antibacterial drugs against various Gram-positive and Gram-negative pathogens, which is of great importance in therapy practice. [ABSTRACT FROM AUTHOR]

Taking into consideration the growing resistance towards currently available antimycobacterials, there is still an unmet need for the development of new chemotherapeutic agents to combat the infectious agents. This study presents X-ray single-crystal analysis to verify the structure of leading sulfonyl hydrazone 3b, which has proven its potent antimycobacterial activity against Mycobacterium tuberculosis H37Rv with an MIC value of 0.0716 μM, respectively, low cytotoxicity, and very high selectivity indexes (SI = 2216), and which has been fully characterized by Nuclear Magnetic Resonance (NMR) and High-Resolution Mass Spectrometry (HRMS) methods. Furthermore, this study assessed the ex vivo antioxidant activity, acute and subacute toxicity, and in vitro inhibition capacity against enoyl-ACP reductase of hydrazones 3a and 3b, as 3a was identified as the second leading compound in our previous research. Compared to isoniazid, compounds 3a and 3b demonstrated lower acute toxicity for intraperitoneal administration, with LD50 values of 866 and 1224.7 mg/kg, respectively. Subacute toxicity tests, involving the repeated administration of a single dose of the test samples per day, revealed no significant deviations in hematological and biochemical parameters or pathomorphological tissues. The compounds exhibited potent antioxidant capabilities, reducing malondialdehyde (MDA) levels and increasing reduced glutathione (GSH). Enzyme inhibition assays of the sulfonyl hydrazones 3a and 3b with IC50 values of 18.2 µM and 10.7 µM, respectively, revealed that enoyl acyl carrier protein reductase (InhA) could be considered as their target enzyme to exhibit their antitubercular activities. In conclusion, the investigated sulfonyl hydrazones display promising drug-like properties and warrant further investigation. [ABSTRACT FROM AUTHOR]

Ester 2 was produced by reacting thiourea derivative 1 with ethyl 2-chloro-3-oxobutanoate in MeOH containing piperidine. Hydrazide 3 was produced by reacting the latter ester with hydrazine hydrate in EtOH at reflux. By reacting hydrazide 3 with aromatic/heterocyclic aldehydes, twelve derivatives of hydrazide hydrazone 5a–l were produced. Spectral measurements and elemental analysis verified the molecular structure. Compounds 2, 5a, 5c, 5d, and 5f had strong effects on all the pathogenic bacterial strains according to an evaluation of the antimicrobial qualities of the synthetic compounds. With inhibitory zone diameters ranging from 16 to 20.4 mm, hydrazide hydrazone 5f exhibited the strongest activity. Additionally, the minimum inhibitory concentration (MIC) was assessed. The best outcomes were found with hydrazones 5c and 5f. For B. subtilis, the MIC of 5c was 2.5 mg/mL. For E. coli and K. pneumoniae, the MIC of 5f was 2.5 mg/mL. The molecular mechanics-generalized born surface area (MM/GBSA) was utilized to compute binding free energies via a molecular dynamics simulation analysis of the most active compounds, 5f and 5c. Moreover, computational analyses demonstrated that 5f had a substantial affinity for the active site of DNA gyrase B, suggesting that this compound could be a strong platform for new structure-based design efforts. [ABSTRACT FROM AUTHOR]

A series of novel Schiff base derivatives (1–28) of 3,4-dihydroxyphenylacetic acid were synthesized in a multi-step reaction. All the synthesized Schiff bases were obtained in high yields and their structures were determined by 1HNMR, 13CNMR, and HR-ESI–MS spectroscopy. Except for compounds 22, 26, 27, and 28, all derivatives show excellent to moderate α-glucosidase inhibition. Compounds 5 (IC50 = 12.84 ± 0.52 µM), 4 (IC50 = 13.64 ± 0.58 µM), 12 (IC50 = 15.73 ± 0.71 µM), 13 (IC50 = 16.62 ± 0.47 µM), 15 (IC50 = 17.40 ± 0.74 µM), 3 (IC50 = 18.45 ± 1.21 µM), 7 (IC50 = 19.68 ± 0.82 µM), and 2 (IC50 = 20.35 ± 1.27 µM) shows outstanding inhibition as compared to standard acarbose (IC50 = 873.34 ± 1.67 µM). Furthermore, a docking study was performed to find out the interaction between the enzyme and the most active compounds. With this research work, 3,4-dihydroxyphenylacetic acid Schiff base derivatives have been introduced as a potential class of α-glucosidase inhibitors that have remained elusive till now. [ABSTRACT FROM AUTHOR]

Breast cancer is associated with high mortality and morbidity rates. As about 20–30% of patients exhibiting ER-positive phenotype are resistant to hormonal treatment with the standard drug tamoxifen, finding new therapies is a necessity. Postbiotics, metabolites, and macromolecules isolated from probiotic bacteria cultures have been proven to have sufficient bioactivity to exert prohealth and anticancer effects, making them viable adjunctive agents for the treatment of various neoplasms, including breast cancer. In the current study, postbiotics derived from L. plantarum and L. rhamnosus cultures were assessed on an in vitro breast cancer model as potential adjunctive agents to therapy utilizing tamoxifen and a candidate aziridine–hydrazide hydrazone derivative drug. Cell viability and cell death processes, including apoptosis, were analyzed for neoplastic MCF-7 cells treated with postbiotics and synthetic compounds. Cell cycle progression and proliferation were analyzed by PI-based flow cytometry and Ki-67 immunostaining. Postbiotics decreased viability and triggered apoptosis in MCF-7, modestly affecting the cell cycle and showing a lack of negative impact on normal cell viability. Moreover, they enhanced the cytotoxic effect of tamoxifen and the new candidate drug toward MCF-7, accelerating apoptosis and the inhibition of proliferation. This illustrates postbiotics' potential as natural adjunctive agents supporting anticancer therapy based on synthetic drugs. [ABSTRACT FROM AUTHOR]

Herein, the constructing synthon 3‐oxobutanamidothiophene derivatives 2 a and 2 b were synthesized and utilized for building a wide variety of pyran, thiazole, pyrazole or pyrimidine ring heterocyclic compounds that can be used as anticancer medications. 3‐Oxobutanamidothiophene derivatives 2 a,b were coupled with 4‐substitutedphenyl diazonium chloride to produce the corresponding hydrazones derivatives 3 a–f. Various thiophene‐pyran derivatives 4 a,b were synthesized through the treatment of thiophene components 2 a,b with different arylidene‐malononitrile. 2‐Aminothiophene derivatives 5 were prepared via Gewald's reaction between 2 a,b, elemental sulfur, and various activated nitrile derivatives. The 3‐oxobutanamidothiophene derivatives 2 a,b were reacted with PhNCS and the potassium salt intermediates 6 a,b with ethyl bromoacetate to pick up the corresponding thiophene‐thiazolidin‐4‐one derivatives 7. Treatment of the conforming thiocarbamoyl compounds 8 a,b, which undergo heating with three types of α‐halogenated reagents to afford the corresponding substitutedthiophene‐3‐carboxamides 9 a,b. Condensation of keteneN,S‐acetals 10 a,b with hydrazines furnished the thiophene‐pyrazole‐4‐carboxamide hybrids 11 a,b, while condensation with urea and/or thiourea afforded the corresponding thiophene‐pyrimidine‐5‐carboxamides 12 a,b. The recently synthesized thiophene compounds were characterized there in vitro anticancer properties against HepG2 (hepatocellular carcinoma) and MDA‐MB‐231 (breast cancer) were evaluated. Molecular docking was also performed to predict the binding modes of synthesized derivatives with the good anticancer results designed as potential inhibitors for a specific target. [ABSTRACT FROM AUTHOR]

Treatment of isatin with ammonia in methanol under reflux, followed by hydrazine substitution of the methoxy group afforded isamic hydrazide in up to 79 % yield. Subsequent condensation of isamic hydrazide with selected aromatic ketones and aldehydes gave access to novel 2‐oxo‐1,2‐dihydro‐1′H‐spiro[indoline‐3,2′‐quinazoline]‐4′‐carbohydrazones (4–11) in yields between 59 % and 74 %. Detailed structural analysis of synthesized compounds was done using spectroscopic techniques. Antibacterial screening of the hydrazone derivatives (4–11) demonstrated broad‐spectrum activity against evaluated bacterial strains, with inhibition zones ranging from 10 to 32 mm. Specifically, compound 9 exhibited superior activity compared to the standard streptomycin against various bacterial strains, including B. polymyxa (LIO), B. cereus (NCBI 6349), C. pyogenes (LIO), B. subtilis (NCBI 3610), S. aureus (NCBI 8588), E. coli (NCIB 86), P. aeruginosa (NCIB 950), and K. pneumoniae (NCIB 418). Moreover, the inhibitory concentrations of compound 9 were lower than those of streptomycin, underscoring its efficacy as a potential antibacterial agent. These findings suggest that the synthesized hydrazone derivatives possess significant potential as novel and effective antibacterial agents, warranting further exploration in the field of antibacterial drug development. [ABSTRACT FROM AUTHOR]

N-(Iminyl)pyridinium salts are a rare and poorly explored class of pyridine derivatives. In this work, we propose a method for the synthesis of these compounds from methyl nicotinate and hydrazones of aromatic ketones. The method involves N-arylation of pyridine with 2,4-dinitrophenol tosylate and subsequent reaction of the arylpyridinium salt with the amino group of N-unsubstituted hydrazones (the Zincke reaction). [ABSTRACT FROM AUTHOR]

Copyright of Erzincan University Journal of Science & Technology is the property of Erzincan Binali Yildirim Universitesi and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

Given the importance of molecular structure in pharmacological activity and interaction with biological receptors, we conducted a study on the 3,4-dihydroxybenzaldehyde hydrazone derivative of 5-methoxy-indole carboxylic acid (5MICA) and a newly synthesised analogue bearing a 2-methoxy-4-hydroxyphenyl ring using single-crystal X-ray diffraction. We studied the ability of the two compounds to scavenge hypochlorite ions using luminol-enhanced chemiluminescence and their potential to modulate oxidative damage induced by iron on the biologically significant molecules lecithin and deoxyribose in order to evaluate possible antioxidant and prooxidant effects. The X-ray study revealed highly conserved geometry and limited rotation and deformation freedom of the respective indole and phenyl fragments. Interestingly, a conformational difference between the two independent molecules in the asymmetric unit of 3b was found. The X-ray study revealed a combination of hydrogen bonding interactions, short contacts, and π–π stacking stabilizing the specific three-dimensional packing of the molecules of 3a and 3b in the crystal structures. The three-dimensional packing of the molecules of 3b produced a zigzag layering projected along the c-axis. Both compounds effectively decreased luminol-dependent chemiluminescence in model systems with KO2-produced superoxide. They displayed opposite effects when applied in a xanthine/xanthine oxidase system. The hydrazones of 5MICA do not trigger a prooxidant effect or subsequent toxicity under conditions of iron-induced oxidative stress. The 3,4-dihydroxy-substituted derivative demonstrated excellent radical scavenging properties in all model systems, making it the lead compound for the development of compounds with combined neuroprotective and antioxidant properties. [ABSTRACT FROM AUTHOR]

A new series of 2H‐chromene‐based hydrazones (10 a–w, 12 a–d, and 14 a–d) were efficiently synthesized by the reaction of substituted 2H‐chromene aldehydes (8 a–w) with various hydrazines (9, 11, and 13) in absolute ethanol under microwave irradiation as well as by lemon juice mediated conventional heating. The structures of synthesized target molecules were identified by spectroscopic analysis methods (1H NMR, 13C NMR, FT‐IR, and HRMS). The in vitro anticancer activity of the new 2H‐chromene‐based hydrazones were evaluated on the three breast cancer cell lines (MCF‐7, MDA MB‐231, and MDA MB‐468) by MTT assay. Among these synthesized compounds, 10 r and 12 b exhibited the most potent antiproliferative activities with IC50 values at 9.12±0.45 μM and 10.71±0.67 μM respectively, against MCF‐7 cell. Flowcytometric analysis revealed that these two potent compounds, 10 r and 12 b arrested the cell cycle at the G2/M phase and induced apoptosis of proteins in a dose‐dependent manner. It was further confirmed by Hoechst staining and Annexin V‐FITC assay. Additionally, compounds 10 r and 12 b were examined by in silico molecular docking, which revealed that compound 10 r displayed excellent binding affinity energy of around −10 kcal/mol with human HER2 receptor. Also, the ADME studies validated the hybrid compounds showing promising physicochemical, pharmacokinetic, and drug‐like attributes. Broadly, these results underscored the potential of 2H‐chromene‐based hydrazone derivatives as promising anticancer agents. [ABSTRACT FROM AUTHOR]

This paper includes the synthesis of new imidazolidine-4-one and thiazolidine-4-one derivatives derived from 4-(2,4-dichlorophenoxy) butyric acid (1) by multistep reaction, the first step synthesis ester (2) by the esterification reaction of 4-(2,4-dichlorophenoxy) butyric acid with ethanol in the presence of sulfuric acid. Ester namely ethyl 4-(2,4-dichlorophenoxy) butanoate (2) was converted to the corresponding 4-(2,4-dichloro phenoxy)butane hydrazide (3) by reaction with hydrazine hydrate after those hydrazones (4a-f) derivatives were obtained by the reaction of carboxylic acid hydrazide (3) with various substituted aromatic aldehydes, this hydrazone were used to synthesize some new heterocyclic compounds by the hydrazones (4a-f) with Phenyl Alanine and thioglycolic acid to prepare imidazolidine-4-one(5a-e) and thiazolidine-4-one (6a-d) compounds respectively. The molecular docking study was carried out with the essential enzyme Insulin (PDB 1i144) responsible for Diabetes, suggesting that (4a-e) are the most active derivatives of the series that is responsible for diabetes, for some of the compounds that were prepared in this study. It was found that compounds (4a-e) are the most active derivatives. All newly synthesized compounds in this study were confirmed by physical and spectral (FT-IR, ¹H NMR, and 13C NMR) analysis. [ABSTRACT FROM AUTHOR]

According to the interesting reactivity of arylhydrazones in coordination chemistry and biological assays, malonyl dihydrazone ligand of diisatin derivative (H2Lm) was reacted with Cu2+ and Zn2+ ions forming two complexes of dinuclear homoleptic mode (CuLm and ZnLm, respectively). Demonstration of their chemical structures was confirmed through various spectroscopic ways alongside the elemental analyses (EA), conductivity measurements, and magnetic characteristics. Their bio‐performance was recorded based on their inhibited potential of the growing ability of some common bacteria, fungi, and human cancer/normal cell lines. The biological studies appointed the role and job of M2+ ion = Cu2+ or Zn2+ in its chelated MLm complex to perform the bio‐reactivity over the free ligand, H2Lm. Moreover, their interacted modes with ctDNA (i.e., calf thymus DNA) were examined via the viscometry and spectrophotometric titration. Because the two chelates (CuLm and ZnLm) represented an attractive job for the inhibited action against the current microorganisms and the human cancer/normal strains' growth over the free H2Lm ligand, CuLm and ZnLm complexes displayed a distinguished interaction with ctDNA more than that of their uncoordinated H2Lm ligand. From the values of binding constant (Kb) and Gibb's free energy (∆Gb≠), CuLm assigned more bio‐action within ctDNA more than ZnLm H2Lm ligand, referring to the role of Cu2+ ion with more electronegativity to enhance the reactivity of CuLm over their free H2Lm ligand and ZnLm. The catalytic behavior of CuLm and ZnLm was given within the epoxidation of 1,2‐cyclohexene (an example of unsaturated hydrocarbons) homogeneously using hydrogen peroxide (the oxidant). Their catalytic action was optimized through various temperatures, solvents, time, and type of M2+ ion in the catalyst. [ABSTRACT FROM AUTHOR]

[Display omitted] • A new hydrazone derivative inhibits steel rebar corrosion in chloride-contaminated SCPS. • The tested inhibitor exhibits an excellent corrosion protection for 720 h of immersion. • XPS and other characterization techniques confirm the effective adsorption of inhibitor molecules on steel rebar. • SCC-DFTB simulation reveals the formation of chemical bonds between inhibitor molecules and iron surface. Corrosion-induced deterioration of infrastructure is a growing global concern. The development and application of corrosion inhibitors are one of the most effective approaches to protect steel rebar from corrosion. Hence, this study focuses on a novel hydrazone derivative, (E)-N′-(4-(dimethylamino)benzylidene)-2-(5-methoxy-2-methyl-1H-indol-3-yl)aceto-hydrazide (HIND), and its potential application to mitigate corrosion in steel rebar exposed to chloride-contaminated concrete pore solutions (ClSCPS). The research aims to evaluate the anti-corrosion capabilities of HIND on steel rebar within a simulated corrosive environment, focusing on the mechanisms of its inhibitory effect. The corrosion of steel rebar exposed to the ClSCPS was studied through weight loss and electrochemical methods. The surface morphology of steel rebar surface was characterized by FE-SEM-EDS, AFM; oxidation states of the steel rebar and crystal structures were examined using X-ray photoelectron spectroscopy (XPS) and X-ray diffraction (XRD) methods. Further, experimental findings were complemented by theoretical studies using self-consistent-charge density-functional tight-binding (SCC-DFTB) simulations. The performance of HIND was monitored at an optimal concentration over a period of 30 days. The results indicated a significant reduction in steel rebar corrosion upon introducing HIND. The inhibitor molecules adhered to the steel surface, preventing further deterioration and achieving an inhibition efficiency of 88.4% at 0.5 mmol/L concentration. The surface morphology analysis confirmed the positive effect of HIND on the rebar surface, showing a decrease in the surface roughness of the steel rebar from 183.5 in uninhibited to 50 nm in inhibited solutions. Furthermore, SCC-DFTB simulations revealed the presence of coordination between iron atoms and HIND active sites. The findings demonstrate the potential of HIND as an effective anti-corrosion agent in chloride-contaminated environments. Its primary adsorption mechanism involves charge transfer from the inhibitor molecules to iron atoms. Therefore, applying HIND could be an effective strategy to address corrosion-related challenges in reinforced infrastructure. [ABSTRACT FROM AUTHOR]