Search Results (361)

The design of solar cells with a bulk heterojunction is one of the most promising areas in renewable energy sources. Acceptor dopants with suitable physical characteristics are desirable components for ternary organic solar cells with cascade charge transfer. In this Short Note, 2-(4H-indeno[2,1-d][1,2,3]thiadiazol-4-ylidene)-1H-indene-1,3(2H)-dione was prepared by thionation of [1,2′-biindenylidene]-1′,3,3′(2H)-trione with Lawesson’s reagent in refluxing benzene. The structure of newly synthesized compound was strictly confirmed by spectral methods. The obtained optical and electrochemical properties make this compound a promising candidate for use in ternary organic solar cells. Full article

Flotation of mixed copper oxide–sulfide ores remains challenging due to low natural floatability of oxide minerals and complex interplay between sulfidization and collector adsorption. This study investigated the combined effect of NaHS-assisted sulfidization and 2,5-dimercapto-1,3,4-thiadiazole (DMTD), an azole-based collector, in terms of enhancing copper recovery from a mixed oxide–sulfide ore. The effects of pulp pH, DMTD, NaHS, and sodium metasilicate dosages, together with pulp solid concentration, were evaluated using response surface methodology. The quadratic model showed high predictive capability (R² = 0.9361), identifying NaHS dosage as the most influential factor. Optimum operating conditions (pH 9.50, DMTD 200 g/t, NaHS 750 g/t, sodium metasilicate 500 g/t, and 25% solids) yielded 64.03% copper recovery. Compared with the plant collector (PAX, Potassium Amyl Xanthate), DMTD increased recovery by 12.6% for highly oxidized ore while producing a higher concentrate grade. Density Functional Theory (DFT) calculations provided molecular insights into the experimental observations, confirming DMTD’s high affinity for sulfidized surfaces. Hybrid solvation models revealed greater thermodynamic stability (ΔE_ads = −6.74 eV) than PAX due to hydrogen bonding with explicit water molecules, while the smaller HOMO–LUMO gap (ΔE_gap = 0.86 eV) supported its superior electron transfer capability and reactivity. These findings demonstrate that NaHS-assisted sulfidization with DMTD is an effective strategy for improving flotation of copper oxide–sulfide ores. Full article

Compounds containing electron-withdrawing dicyanopyrazine and 1,2,5-chalcogenadiazole fragments are promising for the design of magnetic and optoelectronic materials. In this paper, bis([1,2,5]thiadiazolo)[3,4-f:3′,4′-h]quinoxaline-8,9-dicarbonitrile was prepared via Körner–Hinsberg condensation of benzo[1,2-c:3,4-c′]bis([1,2,5]thiadiazole)-4,5-dione with 2,3-diaminomaleonitrile in the presence of catalytic amounts of TsOH in refluxing ethanol. The structure of the newly synthesized compound was established via elemental analysis, mass spectrometry, ¹³C NMR, and IR spectroscopy. Full article

Background/Objectives: Biofilm-related infections represent a major concern in clinical practice because of their poor responsiveness to standard antimicrobial treatments. Over the past decade, many efforts have been made to identify new compounds capable of inhibiting this particularly resistant form of bacterial life. Although several compounds have shown interesting anti-biofilm properties, none have reached the clinic. Methods: In the present work, we describe the synthesis and biological assessment as anti-biofilm agents, of a novel library of twenty-one imidazo[2,1-b][1,3,4]thiadiazol-2-yl]-1H-pyrrolo[2,3-b]pyridines. Results: The newly synthesized compounds were in vitro evaluated for their ability to prevent biofilm formation and to eradicate established biofilms in Staphylococcus aureus ATCC 25923 and Pseudomonas aeruginosa ATCC 15442. Additionally, the most potent compounds, 9g and 9u, were in vivo assayed for their safety profile and the anti-infective effect in a Galleria mellonella model. Conclusions: Derivatives 9g, 9i, 9n, 9q and 9u proved to be potent inhibitors of S. aureus biofilm showing BIC₅₀ values lower than 15 µg/mL. Noteworthy, the in vivo results revealed the promising protective properties of compound 9u in the early stage of staphylococcal infection. Full article

Background/Objectives: Diabetes mellitus (DM) is a critical metabolic condition with escalated blood glucose levels caused by insulin resistance, restricted insulin production, and the activity of alpha-amylase and alpha-glucosidase enzymes. Methods: This current work focuses on the synthesis and evaluation of novel Pyrimidine-derived pyrazole-based thiadiazole derivatives to target DM by inhibiting α-amylase and α-glucosidase. Results: The findings exhibited that, except for three compounds, all other synthesized derivatives inhibited α-amylase and α-glucosidase enzymes with IC₅₀ values ranging from 5.17 μM to 29.84 μM on α-amylase and 7.60 μM to 31.62 μM on α-glucosidase, in comparison to the standard drug Acarbose (α-amylase IC₅₀ = 8.25 ± 0.80 μM; α-glucosidase IC₅₀ = 10.75 ± 1.10 μM). Analogs 8g, 8k, and 8b displayed superior or comparable inhibitory activity compared to the reference drug Acarbose. The inhibition potential of the derivatives can be attributed to their stable contacts with crucial amino acid residues of targeted enzymes, as shown through molecular docking analysis. Moreover, DFT-calculated HOMO–LUMO parameters and electrostatic potential (ESP) maps were used to gain complementary insight into the electronic characteristics, charge distribution, and potential interaction behavior of the synthesized derivatives, which supported the molecular docking observations. Conclusions: Experimental outcomes and in silico support display that these derivatives serve as potential leads for anti-diabetic drug development. These potent pyrimidine-derived pyrazole-based thiadiazole derivatives were comparable to an existing diabetic mellitus inhibitor, specifying potential for further therapeutic development and optimization against diabetic mellitus. Full article

Lubricants contain various types of additives, with corrosion and rust inhibitors being some of the most important. Due to the importance of 2,5-Dimercapto-1,3,4-thiadiazole (DMTD) in the field of corrosion inhibitors, we used it as a key intermediate to synthesize a series of 4-thiazolidinone and 4-imidazolidinone derivatives. This work also includes performing the reaction of DMTD with ethyl chloroacetate, which produced the corresponding ester, followed by the conversion into a hydrazide derivative using hydrazine hydrate. The next step is the condensing of the yielded hydrazide with various aromatic aldehydes yielding Schiff bases, which were subjected to cyclization by means of mercapto acetic acid and ethyl glycinate to produce the target 4-thiazolidinone and 4-imidazolidinone derivatives, respectively. FT IR, ¹H NMR, and ¹³C NMR spectroscopies were involved to confirm the structures of these derivatives. The synthesized derivatives have been evaluated as copper corrosion and rust inhibitors for medium lubricants in accordance with ASTM-D130 and ASTM-D665 standards. Interestingly, some lubricant blends of the synthesized derivatives showed good performance as copper corrosion and rust inhibitors. Full article

Background/Objectives: Based on the central nervous system-related activity potential of 1,3,4-thiadiazole derivatives, novel 1,3,4-thiadiazole compounds were synthesized, and their possible antidepressant-like and anxiolytic-like effects were investigated. Methods: The chemical structures of the compounds were elucidated using several spectroscopic techniques. Antidepressant-like effects of compounds were evaluated using the tail suspension and the modified forced swimming tests, while anxiolytic-like effects were assessed using the hole board, elevated plus maze, and open field tests in male Balb/c mice. Motor activities of the animals were examined using the activity-meter device. Mechanistic and computational in silico studies were also performed. Results: The results demonstrated that compounds 4e–4i exhibited antidepressant-like effects, whereas only compound 4e showed an anxiolytic-like effect. None of the compounds produced significant alterations in motor activities of animals, indicating that the observed behavioral effects were specific. The antidepressant-like effects of compounds 4e–4i were abolished by p-chlorophenylalanine methyl ester (PCPA) and α-methyl-para-tyrosine methyl ester (AMPT) pre-administration indicating that the antidepressant-like effects of these test compounds are related to both serotonergic and catecholaminergic mechanisms. Furthermore, the anxiolytic-like effect of compound 4e was reversed by flumazenil and NAN-190 pre-administrations, indicating the participation of the GABA-A benzodiazepine receptor complex and 5-HT_1A receptors in its pharmacological activity. Computational in silico studies revealed that compounds have good ADME profiles; compounds 4e–4i interact with the serotonin transporter; compound 4e shows affinity for GABA-A and 5-HT_1A receptors; and all interactions remain stable under dynamic conditions. Conclusions: These findings supported the previous papers reporting the antidepressant-like and anxiolytic-like effects of 1,3,4-thiadiazole derivatives. Full article

Background/Objectives: The purpose of this study was the chemical design, synthesis, and evaluation of the antimicrobial and antibiofilm potentials of 20 novel thiazolyl-methylthio-thiadiazole hybrid compounds (6a–j and 8a–j). Methods: The compounds were designed as structural analogues of halicin with two points of variation and were synthesized through a process with multiple condensation steps. The compounds were evaluated in vitro through MIC determinations for the antimicrobial activity and percentage of biofilm inhibition, and in silico, respectively, through molecular docking, druggability, and ADMETox prediction. A 2D-QSAR study was conducted for antimicrobial activity using the Free-Wilson model. Results: In terms of antibacterial activity, all compounds displayed important activity on the tested strains (MICs = 15.62–250 μg/mL), except against Staphylococcus aureus. Regarding the antifungal activity, the effect against Candida albicans was similar to fluconazole in most cases (MIC = 15.62 μg/mL). With respect to the antibiofilm activity, the most effective activity was registered against the Pseudomonas aeruginosa biofilm. The in vitro results for the antibacterial activity against Escherichia coli were correlated with the observations drawn in the molecular docking study on the ATPase domain of the GyrB subunit of E. coli. The in silico predictions of the molecular properties concluded that all compounds have good druggability properties, while the ADMETox predictions concluded that the compounds could have low gastrointestinal absorption and blood–brain barrier permeation capacity, but raised safety flags (e.g., hepatotoxicity and high acute oral toxicity). The 2D-QSAR study concluded that the thiazolyl-methylthio-thiadiazole scaffold had the highest contribution to antimicrobial activity in almost all cases. Conclusions: The two series of compounds highlight the impact of structural modulations of the scaffold and its substituents on the investigated biological activities. Full article

The environmental persistence of β-lactam antibiotics represents a growing ecological concern, requiring materials capable of combined adsorption and catalytic degradation. Herein, pure ZnS and 1% Fe-doped ZnS nanoparticles were synthesized via microwave-assisted treatment and evaluated for the removal of ceftaroline fosamil from aqueous media. Transmission electron microscopy revealed quasi-spherical nanoparticles below 10 nm, while selected area electron diffraction confirmed a face-centered cubic structure retained after Fe incorporation. UV-Vis spectroscopy showed similar absorption edges (~316 nm), indicating negligible band-gap variation, whereas photoluminescence analysis demonstrated strong emission quenching in Fe-ZnS, indicating suppressed electron–hole recombination. Point-of-zero charge measurements (pH_PZC ≈ 4.6 for ZnS; 4.5 for Fe-ZnS) indicated negatively charged surfaces under circumneutral conditions, influencing interfacial interactions with the antibiotic. Adsorption experiments followed the Langmuir isotherm model, with Fe-ZnS exhibiting a higher maximum adsorption capacity (156 mg g⁻¹) compared to ZnS (115 mg g⁻¹). Under UV irradiation (302 nm), Fe-ZnS achieved near-complete degradation at a catalyst loading of 500 ppm. Liquid chromatography–mass spectrometry analysis revealed the transformation of ceftaroline fosamil (m/z 685.01) into ceftaroline (m/z 605.05) via phosphate group loss, followed by the formation of intermediate fragments at m/z 492.08 and 308.03, associated with cleavage of the thiadiazol-amine moiety and subsequent opening of the cephalosporin ring. After extended irradiation, these intermediates diminished, and a fragment at m/z 356.01 was detected, suggesting further breakdown through thioether bond cleavage. These results support a degradation pathway involving sequential dephosphorylation and fragmentation of the cephalosporin core. Overall, the enhanced performance of Fe-ZnS arises from the synergistic interplay between surface charge characteristics and dopant-modulated charge carrier dynamics, highlighting its potential for antibiotic remediation in aquatic environments. Full article

Background: Cancer patients are highly susceptible to microbial infections due to immune suppression, necessitating therapeutic strategies that integrate anticancer efficacy with effective antimicrobial intervention. Chalcone-derived nitrogen-fused heterocycles represent a promising platform for developing multi-target agents with relevance to antimicrobial drug delivery, particularly for localized infections. Methods: A series of chalcone-based pyrazoline-thiadiazole nitrogen-fused azole hybrids was synthesized via thiosemicarbohydrazide-functionalized intermediates and fully characterized. Antiproliferative activity was evaluated against MCF-7, HepG-2, HeLa, and HCT-116 cell lines, alongside selectivity toward WI-38 normal fibroblasts. Antibacterial, antibiofilm, and in vivo efficacy were assessed against methicillin-resistant Staphylococcus aureus (MRSA USA300) and Acinetobacter baumannii AB5057. Mechanistic investigations included cell-cycle analysis, apoptosis assays, ERK2, RIPK3, p53, BAX/Bcl-2 quantification, DNA gyrase inhibition, molecular docking, molecular dynamics simulations, and density functional theory calculations. Results: Compound 13 exhibited potent cytotoxicity, particularly against MCF-7 (IC₅₀ = 3.87 ± 0.2 µM), outperforming doxorubicin (IC₅₀ = 4.17 ± 0.2 µM), with high selectivity indices (SI = 10.7 for MCF-7). Mechanistically, compound 13 induced G₂/M arrest (40.16% vs. 14.15% control), increased apoptosis to 32.89%, up-regulated ERK2 (3.17-fold), RIPK3 (11.97-fold), and p53 (3.54-fold), and markedly increased the BAX/Bcl-2 ratio (~42-fold). Compounds 7 and 13 displayed bactericidal activity against MRSA and A. baumannii (MIC/MBC = 10 mg/mL), potent antibiofilm effects, and significant in vivo efficacy in an MRSA skin infection model. Compound 13 reduced bacterial load by ~5 log units, outperforming vancomycin. DNA gyrase inhibition (IC₅₀ = 17.10 ± 0.17 µM) and computational studies supported target engagement. Conclusions: Pyrazoline-thiadiazole-based nitrogen-fused azole hybrids, particularly compound 13, demonstrated quantifiable anticancer and antimicrobial efficacy with strong in vivo validation, supporting their potential as multi-target candidates relevant to antimicrobial drug delivery in infection-prone cancer patients. Full article

Recent findings demonstrate that concentrated sulfuric acid supports rich organic chemistry, including the stability of the canonical DNA bases adenine, thymine, guanine and cytosine. Yet, due to full protonation in concentrated sulfuric acid, these bases may not pair as effectively as they do in water. We are therefore motivated to study nucleic acid bases that pair via hydrophobic and van der Waals interactions instead of canonical hydrogen bonding. Here, we investigate the stability of 14 selected, commercially available alternative nucleobases in concentrated sulfuric acid to evaluate their potential for forming DNA-like polymers in this solvent. The reactivity of compounds 1–14 have not been previously investigated in concentrated sulfuric acid. We incubate the selected compounds in 98% and 81% w/w sulfuric acid and monitor their stability using ¹H and ¹³C NMR spectroscopy over 3 weeks at room temperature. In 98% w/w sulfuric acid, six bases—benzo[c][1,2,5]thiadiazole (1), 2,2′-bipyridine (2), 1,1′-biphenyl (3), 1-methoxy-3-methylbenzene (MMO2) (7) and 1-chloro-3-methoxybenzene (ClMO) (13), and 2,4-difluorotoluene (14)—remain soluble and stable with no detectable degradation. A few compounds show non-destructive reactivity, like sulfonation (compound 3) or H/D exchange (compounds 7, 13, 14). The other compounds react rapidly or are insoluble in 98% w/w sulfuric acid. In 81% w/w sulfuric acid, only compounds 1 and 2 remain stable and soluble, while other selected compounds are insoluble or unstable. Our findings identify a subset of alternative bases stable in concentrated sulfuric acid, advancing efforts towards the design of an example genetic-like polymer in this unusual solvent. Our work further highlights sulfuric acid’s potential for supporting complex organic chemistry, with implications for astrobiology, planetary science of Venus and synthetic biology. Full article

This study details the synthesis, characterization, molecular docking and preliminary biological evaluation of a new heterocyclic compound, 2-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)benzaldehyde. This molecule was designed using an artificial intelligence (AI)-based molecular generative model. It was synthesized through a nucleophilic substitution between 3-chloro-4-morpholino-1,2,5-thiadiazole and 2-hydroxybenzaldehyde. Structural elucidation was performed using ¹H NMR, ¹³C NMR, Elemental Analysis, and Single Crystal X-ray diffraction. AI-guided in silico predictions suggested promising pharmacophoric features and potential biological activity. Preliminary biological evaluation, primarily through anticancer assays, demonstrated moderate to significant activity, supporting further investigation. The findings therefore suggest that this AI-generated molecule could serve as a lead scaffold for developing drugs targeting cancer and other infectious diseases. Full article

Background/Objectives: Breast cancer is the most common cancer and the second leading cause of cancer death in women. The aromatase enzyme plays a role in estrogen biosynthesis and is an important biological target for breast cancer treatment. For this purpose, some new 1,3,4-thiadiazole (4a–4j) and 1,2,4-triazole (5a–5j) structures were designed and synthesized based on the structures of the existing aromatase inhibitors letrozole and anastrozole. Methods: The antiproliferative activities of the compounds were tested against MCF-7 cancer cells. The NIH3T3 healthy cells were used to evaluate the selectivity of the compounds. The inhibitory activities of all compounds were tested against the aromatase enzyme. Results: The 1,2,4-triazole derivatives 5b, 5c, 5e, 5f and 5g exhibited the highest antiproliferative activity against MCF7 cells with IC₅₀ values ranging from 3.142 to 10.415 μM. Similar to the antiproliferative activity results, triazole derivatives 5b, 5c, 5e, 5f and 5g exhibited comparable anti-aromatase activity to letrozole (IC₅₀ = 0.031 μM) with IC₅₀ values ranging from 0.064 to 2.224 μM and demonstrated the highest anti-aromatase activity within the series. The interactions of compound 5c, the most potent compound based on activity results, with the aromatase enzyme have been elucidated through molecular docking and MD simulation studies. Conclusions: According to experimental studies and molecular docking findings, compound 5c shows promise for further studies with its aromatase enzyme inhibitory potential. Full article

The anti-inflammatory scaffold 5-aminosalicylic acid, which is widely used in therapeutic applications, was chosen for the synthesis of N-[3-(hydrazinecarbonyl)-4-hydroxyphenyl]acetamide (1) to enhance its antibacterial properties. The condensation of hydrazide 1 with aromatic aldehydes provided hydrazone derivatives 2a–f, whereas cyclocondensation reactions and other related transformations afforded five-membered heterocycles, including pyrrole 3, pyrazole 4, pyrrolidinone 7, oxadiazoles 9, 10, thiadiazole 14, and triazole 15. Additional modifications yielded acetylhydrazine derivative 11, which was O-alkylated to analogue 12. Antibacterial evaluation showed stronger activity against Gram-positive bacteria such as S. aureus and MRSA than against Gram-negative strains of E. coli and S. Enteritidis, consistent with differences in cell membrane permeability. Notably, derivatives containing pyrrolidinone 7, thiosemicarbazide 13, and 1,3,4-thiadiazole 14 exhibited potent bactericidal activity against S. aureus and MRSA, while hydrazones 2b, 2c, 2f, pyrrole 3, and pyrrolidinone 7 exhibited activity against E. coli. These results provide a practical strategy for the discovery of heterocyclic compounds and emphasise the potential of functionalised 5-aminosalicylic acid derivatives as prime candidates for the development of broad-spectrum antibacterial agents. Full article

Owing to the intramolecular push-pull electron effect between the electron donor (D) unit and electron acceptor (A) unit, the D-A type based polymer donors display outstanding device performance. However, the imperfect energy levels lead to the D-A-type-based polymer device exhibiting high voltage loss. In this study, an A1-A2-type copolymer M1 was developed with 1,3-bis(2-ethylhexyl)-5,7-di(thiophen-2-yl)benzo[1,2-c:4,5-c’]dithiophene-4,8-dione (BDD) as the A1 unit and dithieno[3′,2′:3,4;2″,3″:5,6]benzo[1,2-c][1,2,5]thiadiazole (DTBT) as the A2 unit. Compared with D-A-type-based polymer donor PM6, the A1-A2 type based M1 possesses lower energy levels, broader absorption, and stronger crystallinity. After introducing M1 to the PM6:L8-BO-based system as the guest material, the ternary blend films exhibited exceptional face-on molecular orientation and favorable active-layer morphology, which promotes exciton dissociation and suppresses charge recombination. Consequently, the PM6:M1(5%):L8-BO-based ternary device exhibited an impressive power conversion efficiency (PCE) of 19.70% with simultaneously enhanced photostability, which is superior to the PM6:L8-BO-based binary system. Our work offers an efficient approach to developing high-performance ternary devices by introducing a novel A1-A2 type polymer donors as the guest material. Full article