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We present a visible light-mediated dual C–H sulfenylation of imidazopyridines using thiocyanate salt as a sulfur source. This method achieves regioselective thiocyanation of imidazopyridines, which are subsequently converted to bis(imidazopyridine)disulfanes upon base treatment. The disulfides are further transformed into thioethers via nucleophilic attack of indoles, azaindole, benzothiazole, and additional imidazopyridines. The antioxidant properties of selected imidazopyridine derivatives were assessed using the DPPH assay, demonstrating notable potential for therapeutic applications. [ABSTRACT FROM AUTHOR]

Benzothiazole derivatives, a class of heterocyclic compounds, hold significant relevance in medicinal chemistry, materials science, and agrochemicals due to their diverse biological activities and applications. The conventional synthetic routes often involve harsh conditions and generate significant waste, prompting the exploration of more sustainable approaches. This work offers a comprehensive analysis of the developments in the use of heterogeneous catalysts for the production of benzothiazole derivatives, covering research from 2013 onward. Compared to traditional techniques, heterogeneous catalysts provide improved sustainability, efficiency, and recyclability. The review covers many heterogeneous catalysts and discusses their selectivity, recyclability, and catalytic activity. The utilization of heterogeneous catalysts is noteworthy as it facilitates the synthesis process's overall sustainability by allowing for milder reaction conditions, less environmental effect, and easier catalyst separation and recovery. The potential of heterogeneous catalysis in promoting the production of benzothiazole derivatives and satisfying the increasing need for these substances in various industrial applications is also highlighted. [ABSTRACT FROM AUTHOR]

We report the design, synthesis and characterization of a perylene diimide-hydroxyphenyl benzothiazole (BT-PDI) dyad as a new class for the formation of radical anion (BT-PDI˙−) and dianion (BT-PDI2−) in aqueous medium using H2S. We demonstrate the applications of BT-PDI˙− for (i) the detection of H2O2; (ii) the detection of glucose in blood serum using a biochemical assay and (iii) the reduction of Ag+ to Ag0. [ABSTRACT FROM AUTHOR]

Benzothiazole alkaloids are a class of rare heterocyclic alkaloids with unique structures and exhibit a wide range of biological activities. So, the aim of this work is to investigate structural diversity‐guided N‐S heterocyclic derivatives based on natural benzothiazole alkaloids as potential cytotoxic agents. Three series of novel benzothiazole derivatives, including 22 compounds, were designed and synthesized using pharmacophore hybridization, and their in vitro cytotoxic activities against Huh‐7 and A875 were fully evaluated. The results indicated that some of these benzothiazole derivatives had significantly good cytotoxic activities against two tested cell lines compared with the positive control 5‐fluorouracil, and other compounds 3f–3i displayed good selectivity between A875 and Huh‐7 cell lines, which might be used as promising lead molecule for discovery of novel benzothiazole‐type cytotoxic agents. [ABSTRACT FROM AUTHOR]

Anti-microbial resistance has emerged as the leading cause of death worldwide with the rise of multidrug-resistant (MDR) bacteria, the need for novel anti-microbials to treat serious illnesses has become a great necessity. Hence, in this study, we aimed to design and synthesize benzothiazole-coupled azetidinone derivatives (GD1-GD12) as novel antibacterial agents. The synthesized compounds were elucidated by nuclear magnetic resonance, infrared and mass spectroscopy. The antibacterial activities of these compounds were tested against antibiotic-susceptible and MDR strains of bacteria. In addition, we performed ADME profiling, molecular docking and molecular dynamic simulations, principle component analysis, dynamic cross-correlation map and free-energy landscape to assess the binding of synthesized compounds with the β -lactamase. Among the synthesized compounds GD6 and GD5 displayed minimum inhibitory concentrations of 12.5 μ g/mL and 50 μ g/mL against MDR strains of E. coli; more effective than standard. The molecular docking of designed molecules was performed against μ -lactamase enzyme and the stability of the complex was vali-dated. The pharmacokinetic profile displayed the compounds to possess druggable properties within the suitable ranges. The in silico approach displayed compound GD6 to be stable with β -lactamase enzyme; indicating the mechanism for these compounds to be via inhibition of β -lactamase. The novel anti-microbial compounds assessed against susceptible and MDR strains of bacteria possess antibacterial potential via the inhibition of β -lactamase. The aforementioned data will be crucial to the development of novel broad-spectrum antibacterial compounds. A novel method was used to design the ligands: Benzothiazole-coupled azetidinone (GD1-12). Their binding affinity and stability to the β -lactamase enzyme inhibitor (3FV7) were assessed using molecular docking and dynamics. Subsequently, compounds (GD1-12) were synthesized, purified, characterized, and tested for antimicrobial activity. Among all the compounds, GD6 exhibited promising antimicrobial activity. [ABSTRACT FROM AUTHOR]

The present article demonstrates the regioselective synthesis, characterization, and biological evaluation of eighteen novel pyrazolo‐benzothiazole hybrid molecules 5a–5r. We have utilized β,β‐ditosyloxy ketone protocol to synthesize these hybrid molecules. The synthesized compounds were tested for their in‐vitro antiproliferative activities using MTT assay against breast cancer (MCF‐7), cervical cancer (HeLa), and Lung cancer (A549) cell lines. Hybrid molecules 5a, 5m, 5n, and 5o with IC50 values of 0.359 mM, 0.051 mM, 0.079 mM, and 0.259 mM respectively exhibited admirable growth inhibitory properties against MCF‐7 cancer cells which are even better than reference carboplatin drug having IC50 (0.439 mM). Compound 5k with IC50 value of 0.765 mM was found to be the most potent antiproliferative agent for the HeLa cancer cells. Moreover, hybrid molecule 5f with IC50 value of 0.706 mM exhibited better inhibitory activity against A549 cancer cells in comparison to the reference carboplatin drug having IC50 (0.805 mM). The mechanism of cellular toxicity was studied using the Annexin V‐FITC/PI double staining method and cell cycle assay. Molecular docking studies for all the synthesized compounds have also been performed in the binding pocket of VEGFR2 sites (PDB code: 4ASD). Finally, the ADMET profile of the potent molecules was investigated to predict their drug‐likeness behaviour. [ABSTRACT FROM AUTHOR]

In the pickling process and acidizing program for oil wells, the acidic corrosion of metals is a problem that needs to be addressed. Various acid corrosion inhibitors have been studied and used to mitigate the acidic corrosion of carbon steel. In this paper, the corrosion inhibition of 2‐aminobenzothiazole (2 N‐BT), 2‐amino‐4‐hydroxybenzothiazole (2 N4O‐BT), and 2‐amino‐6‐hydroxybenzothiazole (2 N6O‐BT) on carbon steel in 0.5 mol/L HCl was investigated using electrochemical and quantum chemical methods. All three molecules exhibited corrosion inhibition effects. Compared to 2 N‐BT, 2 N4O‐BT and 2 N6O‐BT showed less sensitivity to the environmental conditions and the surface state of the metal. Among them, 0.0010 mol/L 2 N6O‐BT demonstrated the highest and most persistent corrosion inhibition, exhibiting a mixed inhibition mechanism with cathodic inhibition dominance. The adsorption of 2 N6O‐BT on the carbon steel surface was found to be non‐uniform, preferentially adsorbing at certain active sites on the surface, following Freundlich‐Langmuir thermodynamic characteristics. It showed initial strongly adsorbed points and weakly adsorbed regions. With continued adsorption of 2 N6O‐BT, the differences between strongly adsorbed points and weakly adsorbed regions decreased. The introduction of hydroxyl groups, especially in 2 N6O‐BT, extended the negative potential region and enhanced the coordination activity of the molecule, generating the orbital distribution that was advantageous to flat adsorption and the formation of feedback bonds. This provided a molecular structural basis for the excellent corrosion inhibition properties of 2 N6O‐BT. [ABSTRACT FROM AUTHOR]

Over the course of three decades, benzimidazole as well as benzothiazole and its derivatives have been extensively investigated in oligo‐nucleotide therapy for their properties. These derivatives serve as valuable building blocks for creating pharmaceutical and biologically active molecules. With applications ranging across various therapeutic domains, including antiulcer, anticancer, and anthelmintic treatments, substituted benzimidazole/ benzothiazole derivatives have proven their versatility. This review provides a systematic and comprehensive overview of the latest advancements in benzimidazole/ benzothiazole‐based compounds within medicinal chemistry. These compounds exhibit diverse pharmacological activities such as anticancer, antibacterial, antifungal, anti‐inflammatory, analgesic, anti‐HIV, antioxidant, anticonvulsant, antitubercular, antidiabetic, antileishmanial, antihistaminic, antimalarial properties, among others. By presenting insights into the substitution patterns around the benzimidazole/benzothiazole nucleus, this review aims to assist medicinal chemists in developing structure–activity relationships (SAR) for benzimidazole/benzothiazole‐based drugs and compounds, thereby aiding in the advancement of medicinal research. [ABSTRACT FROM AUTHOR]

Neurodegenerative disorders are caused by the progressive death of neuronal cells in specific regions of the brain and spinal cord. The most common neurodegenerative disorders are Alzheimer's disease and Parkinson's disease. The inhibition of enzymes that metabolise neurotransmitter amines is an important approach in the treatment of these disorders and monoamine oxidase (MAO) B inhibitors have thus been used for the treatment of Parkinson's disease. Inhibitors of the MAO-A isoform, in turn, are used clinically for the treatment of affective (e.g., major depression) and anxiety disorders. Recent studies have shown that benzothiazole derivatives act as potent MAO inhibitors. Based on these findings, the present study group synthesised thirteen 2-methylbenzo[d]thiazole derivatives and evaluated their in vitro MAO inhibition properties. The results showed that the benzothiazole derivatives were potent and selective inhibitors of human MAO-B, with all compounds exhibiting IC50 values < 0.017 µM. The most potent MAO-B inhibitor (4d) had an IC50 value of 0.0046 µM, while the most potent MAO-A inhibitor (5e) had an IC50 value of 0.132 µM. It may be concluded that active benzothiazole derivatives may serve as potential leads for the development of MAO inhibitors for the treatment of neuropsychiatric and neurodegenerative disorders. [ABSTRACT FROM AUTHOR]

An efficient I2 (10 mmol %)/H2O2 mediated oxidative formal [4+1] cyclization of 2‐pyridinemethylamine or o‐phenylenediamine (2‐aminobenzenethiol) with benzaldehyde via C−N bond formation has been developed. This strategy provides a straightforward approach to imidazo[1,5‐a]pyridines, iodo‐substituted imidazo[1,5‐a]pyridines and benzimidazole (benzothiazole) derivatives in yields ranging from 60 % to 98 %, respectively. Several heterocyclic products exhibit promising blue luminous performance with satisfactory fluorescence quantum yields of up to 64 %, large Stokes shifts, and a longer lifetime (7.35 ns). The band gap energies obtained from DFT are also consistent with the absorption spectra. [ABSTRACT FROM AUTHOR]

The nanoconfinement effect plays an important role in chemical reactions. Inspired by enzymes, this work presents a new way to conduct the rapid flow synthesis of benzothiazoles in the two-dimensional (2D) nanoconfined space created by a graphene oxide membrane. The conversion reaches 96.7% in a short reaction time of less than 23 s at 22 °C. [ABSTRACT FROM AUTHOR]

Reported here is the iridium-catalyzed regio- and enantio-selective secondary benzylic C–H borylation using benzothiazole as the directing group. Various monosubstituted 2-arylalkylbenzo[ d ]thiazole were well-tolerated, affording the corresponding products in moderate to good yields with good enantioselectivity. The C–B bond in one boryl-ated product could undergo stereospecific transformations to form a series of C–C and C–heteroatom bonds. [ABSTRACT FROM AUTHOR]

The metalation of 1,3-diaryl-4-(arylsulfanyl)imidazolium and 1,3-diaryl-4-(arylsulfonyl)imidazolium chlorides with copper(I) oxide has been studied. The resulting Cu/NHC complexes have been studied as catalysts for the carboxylation of phenylacetylene, benzoxazole, and benzothiazole. The main patterns of this reaction behavior and the dependence of the catalysis efficiency on the NHC structure were revealed. [ABSTRACT FROM AUTHOR]

Benzazoles, such as benzoxazoles and benzothiazoles, are compounds with important biological and pharmacological activities and important intermediaries in synthesis. This report presents the synthesis of a butanamide derived from linking 5-chloro-2-aminobenzoxazole and 2-aminobenzothiazole via 4-chlorobutanoyl chloride. The corresponding compound N-(benzothiazol-2-yl)-4-((5-chlorobenzoxazol-2-yl)aminobutanamide was obtained at a 76% global yield using accessible starting materials and a methodology in two reaction steps. Furthermore, we conducted docking studies of this compound on 3-TOP protein to explore its potential as an antidiabetic agent. [ABSTRACT FROM AUTHOR]

The recent advances in the green-based design and synthesis of core-shell nanostructures have always been an intriguing arena to scientists due to their compelling application in catalytic fields. This work designed and synthesized a new core-shell nanosphere based on Fe3O4 as a novel, heterogeneous, reusable, efficient, and green catalyst to synthesize benzothiazole derivatives under ultrasonic irradiation. To achieve this goal, initially, fabricated Fe3O4 magnetic nanoparticles via the co-operation method were synthesized as a core, followed by coating with polyethylene glycol (PEG-400). Subsequently, Ni@Murexide complex supported on magnetic nanoparticles is successfully synthesized and reported, modified using 3-chloropropyltriethoxysilane (CPTES) and Murexide (MX) ligand in the Fe3O4@PEG support. The obtained structure of Fe3O4@PEG/MX/Ni was characterized by different analyses such as FT-IR, SEM, EDS, TEM, ICP-OES, XRD, VSM, and TGA. The results illustrated the effect of ultrasonic irradiation and the high efficacy of Murexide as a ligand in catalyzing the formation of benzothiazole derivatives and confirming the findings from the reaction of different derivatives of aromatic aldehyde with electron-withdrawing/donor groups with 2-amino thiophenol through a one-pot process in 10 min under ultrasonic irradiation which shows the non-sensitivity of the process to electronic effects. Furthermore, Fe3O4@PEG/MX@Ni showed great use at least six times with no significant loss in catalyst activity. [ABSTRACT FROM AUTHOR]

Benzothiazole is an amazing small molecule involved in many applications in industrial and pharmaceutical industries to prepare many candidate compounds as effective drugs. In this study, we presented some derivatives of this compound that were prepared easily and quickly with the help of microwaves to minimize time, energy, and finances. The compounds’ cytotoxicity against the two cell lines SK-GT-4 and AMGM5 was examined. The cytotoxic effect of each compound at different concentrations was measured using the MTT assay. Compounds exhibited no potent cytotoxic effects toward the SK-GT-4 cell line. Compounds B1 and B2 had a high IC50 value and good growth inhibition activity against the AMGM5 cell line. According to in silico absorption, distribution, metabolism, and excretion analysis (ADME) prediction studies, the compounds B1, B2, and B3 met Lipinski and were drug-like in most physicochemical parameters. Despite some violations, generally favorable pharmacokinetic properties. It is also assumed that it can potentially become a drug candidate in the future. Various electronic parameters were examined using DFT/WB97XD/6-31++G(d,p), and studies were conducted to support the experimental findings. To estimate the binding modes of compounds B1 and B5, we also performed in silico molecular docking studies.

Background Molecular hybridization in drug design is proved to be very successful approach to provide new chemical entities with potential activities and desirable physicochemical properties. Histone deacetylases (HDACs) are involved in controlling the behavior and acetylation of histone and non-histone proteins and their inhibition causes block of cell growth, differentiation, changes in gene expression, and death. Consequently, HDAC inhibitors may lead to anticytotoxic activity. An approach of synthesizing hybrid molecules of benzothiazole cross-linked with hydroxamic acid via an amino acid or aminoalkanoic acid was considered. This approach is expected to optimize the anticytotoxic activity of the proposed compounds. Methods Hybrid molecules of benzothiazole cross-linked with hydroxamic acid ( 2A-E) were synthesized and their chemical structures were confirmed by spectral analyses (FT-IR, 1H-NMR and 13C-NMR). These were subjected to molecular docking on HDAC8 (PDB ID: 1T69). Computational methods were employed using the SwissADME server to predict the ADME parameters and other physicochemical properties. The cytotoxicity evaluation was performed using MTT colorimetric assay. Results Hybrids ( 2A-E) recorded lower ΔG ( -6.322 to - 9.46) than Vorinostat (SAHA, -5.375). ΔG is an affinity scoring function (kcal/mol) and is employed to rank the candidate poses as the sum of the electrostatic and Van der Waals energies. Benzothiazole cross-linked with hydroxamic acid by a p-aminobenzoic acid ( 2E) has recorded the lowest docking score of -9.460 and this may refer to the possibility of high inhibitory activity. The hybrids showed no violation from Lipinski’s rule and complied with parameters with low possible passive oral absorption and no penetration into BBB. Hybrid molecules of benzothiazole recorded very interesting results, particularly, 2D and 2E which showed significant and remarkable activity. Conclusions Hybrid molecules of benzothiazole cross-linked with hydroxamic acid recorded very interesting results, particularly, compounds 2D and 2E which showed significant and remarkable activity on lung cancer cell line type A549.

The escalating incidence of bacterial resistance to commonly prescribed antibiotics underscores the urgent need for the rapid development of innovative antibacterial medications. Heterocyclic compounds, particularly nitrogen‐containing heterocycles like pyrazoles and thiazoles, have garnered attention for their diverse biological activities, including antimicrobial properties. Here, we present a green and efficient multicomponent synthesis method for fourteen novel benzothiazole‐tethered pyrazole derivatives. Utilizing the deep eutectic solvent glycerol/K2CO3 as a base‐catalytic reaction medium at 70 °C, this synthesis approach yielded promising compounds exhibiting substantial antimicrobial activity against various pathogenic microorganisms such as Staphylococcus aureus, Bacillus cereus, and Candida albicans. Among these, 4‐(benzo[d]thiazol‐2‐yl)‐3‐(4‐nitrophenyl)‐1‐phenyl‐1H‐pyrazol‐5‐amine emerged as the most promising candidate, showcasing significant inhibitory potentials with CZD values of 24 mm, 21 mm, and 26 mm for S. aureus, B. cereus, and C. albicans, respectively. Molecular docking studies further supported the experimental observations, revealing the high binding affinity of the compound to the nitroreductase enzyme with a binding score of −8.5 kcal/mol. These findings underscore the potential of these synthesized compounds as antimicrobial agents and suggest avenues for future research in exploring their structure‐activity relationships and therapeutic applications in combating bacterial infections. [ABSTRACT FROM AUTHOR]

In situ encapsulation of the 2-(2′-hydroxylphenyl)benzothiazole (HBT) fluorophore into organically modified silica (ORMOSIL) is recognized as a potential approach to increase the photocurrent conversion efficiency. Encapsulation resulted in a twisted geometrical configuration of HBT with an efficient charge transfer and increased carrier density, resulting in a 246% photo-response enhancement. [ABSTRACT FROM AUTHOR]

We have studied 2‐(2‐aminophenyl)benzothiazole and related derivatives for their photophysical properties in view of employing them as new and readily tunable organic photocatalysts. Their triplet energies were estimated by DFT calculations to be in the range of 52–57 kcal mol−1, suggesting their suitability for the [2+2] photocycloaddition of unsaturated acyl imidazoles with styrene derivatives. Experimental studies have shown that 2–(2–aminophenyl)benzothiazoles comprising alkylamino groups (NHMe, NHiPr) or the native amino group provide the best photocatalytic results in these visible‐light mediated [2+2] reactions without the need of any additives, yielding a range of cyclobutane derivatives. A combined experimental and theoretical approach has provided insights into the underlying triplet‐triplet energy transfer process. [ABSTRACT FROM AUTHOR]

A domino one–pot synthesis of 2‐(trifluoromethyl) benzothiazole via copper–mediated three–component cascade reaction starting from the easily accessible starting materials such as o‐iodoanilines, methyl trifluoropyruvate, and elemental sulfur is reported. The present strategy displayed a comprehensive substrate scope and good functional group tolerance and enabled access to a variety of substituted 2‐(trifluoromethyl) benzothiazoles. A 2‐(trifluoromethyl) benzoselenazole has also been synthesized utilizing this reaction methodology. [ABSTRACT FROM AUTHOR]

Inspired by the remarkable photochemical and photophysical properties of novel 2-(2'-hydroxyphenyl)benzothiazole (HBT) derivatives that could be potentially applied across various disciplines, in this work, effects of atomic electronegativity of chalcogen elements on excited state hydrogen bond effects and excited state intramolecular proton transfer (ESIPT) reaction of the biphenyl-modified HBT derivatives (i.e. HBT-HH-O, HBT-HH-S and HBT-HH-Se) are focused. By comparing the structural changes and infrared (IR) vibrational spectra of the HBT-HH fluorophores in toluene solvent, combined with the preliminary detection of hydrogen bond interaction by core-valence bifurcation (CVB) index, we can conclude that the hydrogen bond could be strengthened in S1 state, which is favourable for the occurrence of ESIPT reactions. The charge recombination behaviour of hydrogen bond induced by photoexcitation also further illustrates this point. Via constructing potential energy curves (PECs) based on restrictive optimisation and searching transition state (TS) form, we confirm the variations of atomic electronegativity of chalcogen have the regulatory effect on the ESIPT behaviour for HBT-HH derivatives, that is, the lower the atomic electronegativity is more conducive to the ESIPT reaction. [ABSTRACT FROM AUTHOR]

Odors play a key role in animal communication and mate choice. Male urinary odor becomes less attractive to mature females when males get infected or have their immune system activated. The development of the immune response at early stages is related to the production of both pro- and anti-inflammatory cytokines. To explore the chemical basis of the observed differences and analyze the effects of female interactions with the urinary odor of antigen-stimulated males, the males of inbred BALB/c (Th1) and C57BL/6 (Th2) mice were immunized with keyhole limpet hemocyanin (KLH). The odor of male urine collected 3 days after immunization proved to be less attractive to females of both strains compared to the odor of control males. Herewith, BALB/c females sniffed the urine of immunized males less frequently, while C57BL/6 females demonstrated a shorter duration of grooming in olfactory tests with urine of immunized males. The altered response of females to the odor of male urine collected on day 3 after KLH immunization matched antigen-induced modulation of relative levels of volatile organic compounds detected in urine samples by gas chromatography/mass spectroscopy (GC-MS). Males of both strains, after KLH immunization, exhibited an increase in the content of nonanal, benzothiazole, 2-sec-butyl-4,5-dihydrothiazole, and [1,4,5]-oxadithiepane. At the same time, no compounds were found, whose content changed multidirectionally in the urine of males after immunization in a strain-dependent manner. [ABSTRACT FROM AUTHOR]

Introduction: Benzotriazoles and benzothiazoles (BTs) are high-production volume chemicals as well as widely distributed emerging pollutants with potential health risk. However, information about human exposure to BTs and associated health outcomes is limited. Objective: We aimed to characterise exposure to BTs among Czech men, including possible occupational exposure among firefighters, its predictors, and its associations with liver function, serum lipids and oxidative stress. Methods: 165 participants (including 110 firefighters) provided urine and blood samples that were used to quantify the urinary levels of 8 BTs (high-performance liquid chromatography-tandem mass spectrometry), and 4 liver enzymes, cholesterol, low-density lipoprotein, and 8-hydroxy-2'-deoxyguanosine. Linear regression was used to assess associations with population characteristics and biomarkers of liver function, serum lipids and oxidative stress. Regression models were adjusted for potential confounding variables and false discovery rate procedure was applied to account for multiplicity. Results: The BTs ranged from undetected up to 46.8 ng/mL. 2-hydroxy-benzothiazole was the most predominant compound (detection frequency 83%; median 1.95 ng/mL). 1-methyl-benzotriazole (1M-BTR) was measured in human samples for the first time, with a detection frequency 77% and median 1.75 ng/mL. Professional firefighters had lower urinary 1M-BTR compared to non-firefighters. Urinary 1M-BTR was associated with levels of γ-glutamyl transferase (β = − 17.54%; 95% CI: − 26.127, − 7.962). Conclusion: This is the first study to investigate BT exposure in Central Europe, including potentially exposed firefighters. The findings showed a high prevalence of BTs in the study population, the relevance of 1M-BTR as a new biomarker of exposure, and an urgent need for further research into associated adverse health outcomes. [ABSTRACT FROM AUTHOR]

An efficient and practical organocatalyzed asymmetric Mannich/cyclization tandem reaction strategy of 2-benzothiazolimines and 2-isothiocyanato-1-indanones was developed, and novel spirocyclic compounds containing benzothiazolimine and indanone scaffolds were obtained. This chiral thiourea-catalyzed Mannich/cyclization tandem reaction offers chiral spirocyclic compounds with continuous tertiary and quaternary stereocenters in good to high yields (up to 90%) with excellent diastereoselectivities (up to >20:1 dr) and enantioselectivities (up to 98% ee) at −18 ◦C. Additionally, the scaled-up synthesis was also performed with retained yield and stereoselectivity, and a reaction mechanism was also proposed. [ABSTRACT FROM AUTHOR]

A composite film of Ni(II) phthalocyanine bearing four benzothiazole (bs) substituents (2) and carboxylic-functionalised multi-walled carbon nanotubes (2-f-MWCNTs) was drop cast on an Au electrode and heated at 50 °C to form a new Au|2-f-MWCNTs sensor for detection of Hg(II) ions. The redox potentials of 2 were measured by cyclic voltammetry, and the processes were affirmed spectroelectrochemically. The nanocomposite of the 2-f-MWCNTs was characterised by Fourier transform Infrared and Raman spectroscopies, and Scanning electron Microscopy. Its electrocatalysis towards Hg(II) was probed by various voltammetric techniques showing higher Faradaic currents in standard redox solutions than the bare or SAMs of 2. Anodic stripping voltammgrams of Hg2+ ions at the Au|2-f-MWCNTs showed good electrocatalytic activity with a linear range spanning 14.4 μM and 1000 μM, and a precision of ± 4.2%. Electrode selectively detected Hg2+ ions in the presence of Pb2+ and Zn2+ ions, while its SWV scan for a mixture of Hg2+ and Cd2+ showed high background noise. [ABSTRACT FROM AUTHOR]

We report a three-stage scheme (1) Pbt–NH2 + CS2 → (Pbt–NH)2C=S (1) (Pbt = 4-(1′,3′-benzothiazole-2′-yl)phenyl), (2) 1 + PPh3 + I2 → Pbt–N=C=N–Pbt (2), (3) 2 + Ph2PH → (Pbt–N)(Pbt–NH)CPPh2 (3) for the synthesis of a novel luminescent phosphoguanidine 3 with an unprecedentedly high yield (90%) at the last catalyst-free stage. It is demonstrated by the density functional theory (DFT) method that high reactivity of 2, leading to such an yield, is explained by a high electrostatic potential at the central carbon atom. For 3, two polymorphs 3α, 3β and a solvatomorph 3γ·THF are prepared. The structures of 2, 3α, 3β, and 3γ·THF are determined by single-crystal XRD. The tendency of crystals of different phenylbenzothiazole derivatives to form different conformations is explained by the computational (DFT) data indicating that the energy change of the molecule of 3 considered as a function of the torsion angle between phenyl and benzothiazole fragments does not exceed 2 kJ/mol in the –15...30° range. Photophysical properties of 3β and 3γ·THF phases are studied. It is shown that these compounds exhibit photoluminescence with an emission maximum at 510 nm. [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]

2-Pyrazoline containing benzothiazole ring 2-[1-(1,3-benzothiazol-2-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]phenol (BP) have been synthesized for the effective identification of picric acid over other competing nitro compounds using fluorescence technique. The pyrazoline BP showed quenching efficiency as high as 82% comparative to other nitro aromatics. The limit of detection and limit of quantification were found to be 1.1 μM and 3.3 μM. The possible mechanism with the quenched PA detection efficiency was based on fluorescence energy transfer and photoinduced electron transfer. Moreover, the observed results were supported by the optimized structures of the compounds using the DFT/B3LYP/6-311G/LanL2DZ method. Eventually, the pyrazoline derivative BP was further utilized for natural water samples, showing recoveries in the 87.62–101.09% and RSD was less than 3%. [ABSTRACT FROM AUTHOR]

The Research and Development in benzothiazole-based medicinal ingredients have turn into a hastily on the rise and gradually more lively topic. Broad number of compounds having Benzothiazole (BTZ) moiety are involved in the treatment of a various number of diseases with maximum curative potency. This review is aimed to afford modern progress in the synthesis of Benzothiazole analogues associated to the green chemistry. Literature surveys on scientific national and international journals, books as well as electronic resources were performed. Benzothiazole and its moieties containing various numbers of structural multiplicities play evidence in search of different pharmacological actions. This review steadily grants an all-inclusive review in the progressive developments of Benzothiazole-based compounds of medicinal chemistry as antibacterial, Hepatitis-C virus inhibitors, anti-alzheimer’s disease, anti-inflammatory and analgesic, antioxidant, anti-convulsant, anti-diabetic, anti-histaminic, anti-malarial, anti-depressant and other medicinal agents. The wide field of pharmacological activity in creature benzothiazole derivative indicates that this string of compounds is of an unquestionable curiosity. This review is also believed to be extra efficient in finding pathogenic problems and diagnostic analogues is ready to find new-fangled judgment in the chase for drawing of a reduced amount of toxic and additional active Benzothiazole-based drugs. It is projected that this knowledge would give rise and show enormous impact for the growth of synthetic pathways for benzothiazoles with expansion of novel synthetic approaches. [ABSTRACT FROM AUTHOR]

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Introduction: Tire and road wear particles are one of the most abundant types of microplastic entering the environment. The toxicity of tire and road wear particles has been linked to their organic additives and associated transformation products. Tire and road wear particles, and associated tire-derived compounds are introduced to the agricultural environment via atmospheric deposition, irrigation with reclaimed wastewater, and the use of biosolids (treated sewage sludge) as fertilizer. In the agricultural environment, these tire-derived compounds could be taken up by edible plants, leading to human exposure. Methods: Sixteen tire-derived compounds were measured in twenty-eight commercial leafy vegetable samples from four countries. Based on the results, the estimated daily intake of these tire-derived compounds was calculated due to leafy vegetable consumption based on local diets under a mean and maximum concentration scenario. Results: In commercial leafy vegetables, six tire-derived compounds were detected: benzothiazole (maximum concentration--238 ng/g dry weight), 2-hydroxybenzothiazole (maximum concentration--665 ng/g dry weight), 1,3-diphenylguanidine (maximum concentration--2.1 ng/g dry weight), N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (6PPD, maximum concentration--0.4 ng/g dry weight), N-Isopropyl-N-phenyl-4-phenylenediamine (IPPD, maximumconcentration--0.1 ng/g dry weight), and N-phenyl-N-cyclohexylp-phenylenediamine (CPPD, maximumconcentration--0.3 ng/g dry weight). At least one compound was present in 71% of samples analyzed. The estimated daily intake for 1,3-diphenylguanidine ranged from 0.05 ng/person/day in the mean scenario to 4.0 ng/person/day in the maximum scenario; benzothiazole ranged from 12 to 1,296 ng/person/day; 6PPD ranged from 0.06 to 2.6 ng/person/day; IPPD ranged from 0.04 to 1.1 ng/person/day; CPPD ranged from 0.05 to 2.6 ng/person/day. Discussion: Statistical analyses did not reveal correlation between known growth conditions and tire-derived compound concentrations in the leafy vegetable samples. The estimated daily intake via leafy vegetable consumption was generally lower than or comparable to the estimated daily intake via other known sources. However, we show that tire-derived compounds are taken up by foodstuff, and exposure might be higher for other produce. Future studies are needed to uncover pathways of tire-derived compounds from road to food, assess the exposure to transformation products, and investigate the biological effects associated with this exposure. [ABSTRACT FROM AUTHOR]

Herein, we report the synthesis and characterization of the novel 2‐aminoguanidine‐derived Schiff base rhenium(I) compounds: fac‐[Re(CO)3(Hguabs)Br]Br (1) (Hguabs ⋅ Cl=2‐((benzothiazole)methyleneamino)guanidine chloride) and fac‐[Re(CO)3(guaquin)Br] (2) (guaquin=2‐((quinolin‐2‐yl)methyleneamino)guanidine). [ABSTRACT FROM AUTHOR]

To develop a new natural spice of Flos sophorae, we used Cordyceps sinensis strain SCT-1 to ferment Flos sophorae. The fermentation medium formula was optimized through factor screening experiments. The spice obtained under the optimal conditions was evaluated for odor and cigarette flavoring sensory evaluation, and the volatile aroma components were analyzed. The results showed that the optimal fermentation medium was Flos sophorae powder 100 g/L, corn flour 2 g/L, bran 2 g/L and sucrose 2 g/L. The optimal spice obtained exhibied a predominant nutty aroma, supplemented by milk aroma and green aroma. By adding the spice, the cigarette had an increased nutty aroma, sweetness, and a more delicate smoke, while reducing its irritancy. The volatile aroma components, as styrene, (2Z)-2-octen-1-ol, naphthalene, benzothiazole, and methyleugenol, contributed to the aroma of the spice. (E)-2-heptanenal, benzaldehyde, linalool, terpine-4-ol and α-terpineol had a significant contribution to the aroma of this spice. [ABSTRACT FROM AUTHOR]

Diarrhea remains one of the leading causes of mortality worldwide, especially among children. Accumulated evidence has shown that Shigella species are the most prevalent bacteria responsible for diarrhea in developing countries. Antimicrobial therapy is necessary for Shigella infections; however, the development of resistance against current drugs justifies the pressing need to search for alternative medications. In this study, we have applied antibacterial phenotypic screening to identify potent anti-Shigella compounds across a broad chemical diversity, including selected acetaminophen derivatives containing a benzothiazole backbone, and their combination with certain antibiotics. As a result, two acetaminophen derivatives containing a benzothiazole backbone (4a and 4b) inhibited the growth of Shigella flexneri with a common MIC value of 12.5 µg/mL. These compounds were established through a time-kill kinetics study to be potentially bactericidal. Meanwhile, the 2-aminobenzothiazoles (1a and 1b) used for the synthesis of compounds 4 (a and b) were found to be poorly active (MIC: 100 µg/mL) against this pathogen. Combination studies of 4a and 4b with the least effective antibiotics (ceftriaxone and cotrimoxazole) demonstrated synergistic anti-Shigella activity with MIC values decreasing from 12.5 to 0.781 μg/ mL. The present study demonstrates that the azobenzothiazole dyes 4 (a and b) can be repurposed as potential anti-Shigella compounds, thus providing potential chemical pharmacophores for the discovery of drugs against infectious diarrhea caused by Shigella and other enteric pathogens, especially in developing countries. [ABSTRACT FROM AUTHOR]

In this study, the synthesis of N‐(5,6‐methylenedioxybenzothiazole‐2‐yl)‐2‐[(substituted)thio/piperazine]acetamide/propanamide derivatives (3a‐3k) and to investigate their acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and β‐secretase 1 (BACE‐1) inhibition activity were aimed. Mass, 1H NMR, and 13C NMR spectra were utilized to determine the structure of the synthesized compounds. Compounds 3b, 3c, 3f, and 3j showed AChE inhibitory activity which compound 3c (IC50 = 0.030 ± 0.001 µM) showed AChE inhibitory activity as high as the reference drug donepezil (IC50 = 0.0201 ± 0.0010 µM). Conversely, none of the compounds showed BChE activity. Compounds 3c and 3j showed the highest BACE‐1 inhibitory activity and IC50 value was found as 0.119 ± 0.004 µM for compound 3j whereas IC50 value was 0.110 ± 0.005 µM for donepezil, which is one of the reference substance. Molecular docking studies have been carried out using the data retrieved from the server of the Protein Data Bank (PDBID: 4EY7 and 2ZJM). Using in silico approach behavior active compounds (3c and 3j) and their binding modes clarified. [ABSTRACT FROM AUTHOR]

In this study, Schiff bases (SCH-1 and SCH-2) were synthesized from the condensation reaction of 2-aminobenzothiazole with 3-hydroxy-4-methoxybenzaldehyde and 3-hydroxy-4-ethoxybenzaldehyde. Poly(phenoxy-imine)s were synthesized from Schiff bases via oxidative polycondensation by NaOCl (6–14% aqueous solution) as oxidant in alkaline medium and H2O2 (35% aqueous solution) as oxidant in THF medium. The structures characterizations of Schiff bases and poly(phenoxy-imine)s were confirmed by FT-IR, 1H and 13C NMR, CV, UV–Vis and TGA analyses. Limit oxygen index (LOI) and the heat resistance index (THRI) temperature were determined from thermogravimetric measurements of compounds. P-SCH-2-A showed the highest LOI as 45.50 with self-extinguishing according to other polymers (18–30). The optical band gap of P-SCH-2-A was determined to be 1.99 eV. Additionally, the optical band gap energy of compounds were calculated by using the Tauc method. According to the Tauc method, the optical band gap (Eg) value of P-SCH-2-A was calculated to be 2.20 eV. The glass transition temperatures (Tg) and surface properties of poly(phenoxy-imine)s were determined from DSC and SEM analyses, respectively. The weight average molecular weight (Mw) values of P-SCH-1-O, P-SCH-2-O, P-SCH-1-A and P-SCH-2-A were calculated to be 7400, 8400, 3100 and 19,100 g mol−1 from gel permeation chromatography (GPC) measurements. [ABSTRACT FROM AUTHOR]

Background: Benzothiazole derivatives have been reported to possess a wide range of biological activities, including antimalarial activity. This systematic review aims to summarize and evaluate the antimalarial activities of benzothiazole analogs. Methods: We conducted an electronic search using nine databases in October 2017 and subsequently updated in September 2022. We included all original in vitro and in vivo studies that documented the antimalarial activities of compounds containing benzothiazole analogs with no restriction. The risk of bias of each included study was assessed by ToxRTool. Results: Twenty‐eight articles were included in our study, which are in vitro, in vivo, or both. Of these, 232 substances were identified to have potent antiplasmodial activity against various strains of the malaria parasite. Benzothiazole analogs show different antimalarial mechanisms, including inhibition of Plasmodium falciparum enzymes in in vitro studies and inhibition of blood parasites in in vivo studies. Conclusions: Benzothiazole derivatives are promising substances for treating malaria. The structure–activity relationship studies suggest that the substitution pattern of the benzothiazole scaffold plays a crucial role in determining the antimalarial activity of the analog. [ABSTRACT FROM AUTHOR]

Epileptogenic seizures, or status epilepticus (SE), leads to excitotoxic injury in hippocampal and limbic neurons in the kainic acid (KA) animal model of temporal lobe epilepsy (TLE). Here, we have further characterized neural activity regulated methylaminoisobutryic acid (MeAIB)/glutamine transport activity in mature rat hippocampal neurons in vitro that is inhibited by riluzole (IC50 = 1 μM), an anti-convulsant benzothiazole agent. We screened a library of riluzole derivatives and identified SKA-41 followed by a second screen and synthesized several novel chlorinated aminothiazoles (SKA-377, SKA-378, SKA-379) that are also potent MeAIB transport inhibitors in vitro, and brain penetrant following systemic administration. When administered before KA, SKA-378 did not prevent seizures but still protected the hippocampus and several other limbic areas against SE-induced neurodegeneration at 3d. When SKA-377 - 379, (30 mg/kg) were administered after KA-induced SE, acute neural injury in the CA3, CA1 and CA4/hilus was also largely attenuated. Riluzole (10 mg/kg) blocks acute neural injury. Kinetic analysis of SKA-378 and riluzoles' blockade of Ca2+-regulated MeAIB transport in neurons in vitro indicates that inhibition occurs via a non-competitive, indirect mechanism. Sodium channel NaV1.6 antagonism blocks neural activity regulated MeAIB/Gln transport in vitro (IC50 = 60 nM) and SKA-378 is the most potent inhibitor of NaV1.6 (IC50 = 28 μM) compared to NaV1.2 (IC50 = 118 μM) in heterologous cells. However, pharmacokinetic analysis suggests that sodium channel blockade may not be the predominant mechanism of neuroprotection here. Riluzole and our novel aminothiazoles are agents that attenuate acute neural hippocampal injury following KA-induced SE and may help to understand mechanisms involved in the progression of epileptic disease.

The catalytic performance for electrocatalytic CO2 reduction reaction (CO2RR) depends on the binding strength of the reactants and intermediates. Covalent organic frameworks (COFs) have been adopted to catalyze CO2RR, and their binding abilities are tuned via constructing donor‐acceptor (DA) systems. However, most DA COFs have single donor and acceptor units, which caused wide‐range but lacking accuracy in modulating the binding strength of intermediates. More elaborate regulation of the interactions with intermediates are necessary and challenge to construct high‐efficiency catalysts. Herein, the three‐component COF with D‐A‐A units was first constructed by introducing electron‐rich diarylamine unit, electron‐deficient benzothiazole and Co‐porphyrin units. Compared with two‐component COFs, the designed COF exhibit elevated electronic conductivity, enhanced reducibility, high efficiency charge transfer, further improving the electrocatalytic CO2RR performance with the faradic efficiency of 97.2 % at −0.8 V and high activity with the partial current density of 27.85 mA cm−2 at −1.0 V which exceed other two‐component COFs. Theoretical calculations demonstrate that catalytic sites in three‐component COF have suitable binding ability of the intermediates, which are benefit for formation of *COOH and desorption of *CO. This work offers valuable insights for the advancement of multi‐component COFs, enabling modulated charge transfer to improve the CO2RR activity. [ABSTRACT FROM AUTHOR]

Treatment of the Schiff base 2-N-(salicylidene) benzothiazole (SabtH) with palladium chloride afforded the neutral 2-N-(salicylidene) benzothiazole palladium(II) complex. This was then treated with one molar equivalent of either ethylenediamine or 1,10-phenanthroline, yielding the neutral mixed ligand complexes 1 and 2, respectively. The prepared organic ligand and its mixed ligand complexes were characterised via UV-Vis, FTIR, ¹H-NMR, and 13C-NMR spectroscopy. The antiproliferative activities of 1 and 2 were tested against MCF-7 (breast) and HT-29 (colon) cancer cells using an MTT assay. 1 showed strong antiproliferative activity against both MCF-7 and HT-29 cancer cells, with IC50 values of 74.6 ± 8.35 and 174 ± 20.28 µg/mL, respectively. In addition, 2 exhibited the maximum antioxidant activity, with an EC50 value of 1029 ± 196.76 µg/mL. [ABSTRACT FROM AUTHOR]

The article discusses the synthesis of thiazole-fused tricyclic quinazolinone alkaloids and their derivatives, focusing on compounds found in traditional Chinese and Indian herbal medicine. The authors describe their synthetic program and the successful synthesis of various thiazole-fused tricyclic quinazolinones. The article provides information on the physical and chemical properties of the synthesized compounds, including melting points, yields, and spectral analysis results. This information can be useful for researchers studying these compounds and their potential applications. [Extracted from the article]

The current report provides an overview of the rapidly developing class of pyrazolines having a benzothiazole moiety at N1. The synthetic approaches (mainly through the [3 + 2] cyclo-condensation of chalcone analogs with 2-hydrazinobenzothiazole) toward these particular pyrazolines, along with their chemical transformation to pyrazoles through oxidation are outlined. The photophysical properties (absorption and emission spectra) along with their applications as fluorescent chemosensors have been summarized. 1-(2-Benzothiazolyl)pyrazolines exhibit significant fluorescence quenching mostly in the presence of transition metal ions, such as Fe3+, Cu2+, Hg2+, Zn2+, or Ni2+, but also toward Al3+, thus enabling the selective detection of these analytes. In addition, examples of 1-(2-benzothiazolyl)pyrazolines acting as chemosensors for anions such as S2− or F− are also available. Comprehensive examination of the biological properties of 1-(2-benzothiazolyl)pyrazolines shows that members of this class possess either broad or selective significant antimicrobial activity, along with tuberculostatic activity and cytotoxicity that is sometimes better than that of positive controls. The antidiabetic, anti-inflammatory, anthelmintic, and antimalarial activity of these compounds, along with their potential for inhibition of enzymes such as carbonic anhydrase or acetylcholinesterase have been briefly explored. [ABSTRACT FROM AUTHOR]

In this study, a semi-static water exposure method was employed to investigate the early developmental and neurotoxic effects of four benzothiazole substances (BTHs), namely benzothiazole (BTH), 2-mercaptobenzothiazole (MBT), 2-hydroxybenzothiazole (BTON), and 2-aminobenzothiazole (2-ABTH), on zebrafish at an equimolar concentration of 10 μM. The findings revealed that all four BTHs exerted certain impacts on early development in zebrafish. MBT stimulated spontaneous movement in juvenile zebrafish, whereas BTON inhibited such movements. Moreover, all four BTHs hindered the hatching process of zebrafish larvae, with MBT exhibiting the strongest inhibition at 24 h post-fertilization (hpf). Notably, MBT acted as a melanin inhibitor by suppressing melanin production in juvenile zebrafish eyes and weakening phototaxis. Additionally, both BTH and BTON exhibited significantly lower speeds than the control group and other test groups under conditions without bright field stimulation; however, their speeds increased to average levels after percussion stimulation, indicating no significant alteration in motor ability among experimental zebrafish groups. Short-term exposure to these four types of BTHs induced oxidative damage in zebrafish larvae; specifically, BTH-, MBT-, and BTON-exposed groups displayed abnormal expression patterns of genes related to oxidative damage. Exposure to both BTH and MBT led to reduced fluorescence intensity in transgenic zebrafish labeled with central nervous system markers, suggesting inhibition of central nervous system development. Furthermore, real-time quantitative PCR results demonstrated abnormal gene expression associated with neural development. However, no significant changes were observed in 2-ABTH gene expression at this concentration. Overall findings indicate that short-term exposure to BTHs stimulates neurodevelopmental gene expression accompanied by oxidative damage. [ABSTRACT FROM AUTHOR]

The highly efficient synthesis of benzoxazole, benzothiazole and benzimidazole has attracted much attention due to their superior biological activities. However, developing environmentally friendly and poisoning-resistant catalysts in heterogeneous catalytic systems remains a critical challenge. Herein, an atomically dispersed Co1/NC catalyst was fabricated by facile pyrolysis of a zeolitic imidazolate framework (ZnCo-ZIF). The Co1/NC catalyst exhibited excellent oxidation catalysis, sulfur-resistance and reusability performance. The mass specific activity (MSA) of Co1/NC was up to 42.0 mol2-PBO molCo−1 h−1, much higher than that of the Co/NC nano-catalyst (15.6 mol2-PBO molCo−1 h−1). Mechanism studies showed that O2 was activated by atomically dispersed Co active species to form 1O2 and ˙O2−, which were responsible for the dehydrogenation of the key imine intermediates to produce 2-phenylbenzoxazole (2-PBO). The current work represents a novel feasible strategy for the synthesis of bioactive heterocyclic compounds using efficient, stable and green heterogeneous catalysts. [ABSTRACT FROM AUTHOR]