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Introduction: This research aims to explore the molecular composition, antioxidant capabilities, and antibacterial effects of the essential oils from Tetraclinis articulateata and Juniperus phoenicea. Methods: Essential oils were extracted using hydrodistillation. Gas chromatography combined with mass spectrometry was used to determine the chemical makeup of essential oils. Two methods are used to assess the antioxidant activity of essential oils: the reduction of iron (ferric reducing antioxidant power or frap) and the trapping of the free radical 2,2-Diphenyl-1Picrylhydrazyl (DPPH). The antimicrobial potential of essential oils was assessed using the diffusion method on a solid-state disk in comparison to nine bacterial and seven fungal souches. Results and Discussion: The essential oil yields from Tetraclinis articulata and Juniperus phoenicea are 0.46% ± 0.02% and 0.83% ± 0.05%, respectively. According to CG/SM's chromatographic analyses, the predominant constituent in the essential oil of J. Phoenicea is α-pinene (59.51%), while the main constituents in the essential oil of T. Articulata? are Bornyle acetate (18.91%) and camphor (28.48%). The assessment of antioxidant activities reveals intriguing antioxidant qualities in the essential oils of the species under investigation. T. Articulata essential oils yield the greatest results in the DPPH and FRAP tests, with CI50 values of around 266.9 ± 5.4 μg/mL and EC50 values of 433.16 ± 4.13 μg/mL, respectively. Except for Staphylococcus epidermidis, Staphylococcus aureus BLACT, and Pseudomonas aeroginosa, the two essential oils have demonstrated significant bactericidal activity against all bacterial and fungal souches (MIC <2 mg/mL et MBC <3.5 mg/mL). The inhibiting effect of these oils on bacterial and fungal development raises potential application areas in the food,cosmetic,and pharmaceutical industries. In addition, the current study investigated the potential antifungal, antibacterial, and antioxidant activities of the essential oils from Juniperus phoenicea and Tetraclinis articulate plants via the Glide molecular docking methodology, and most of these constituents were observed to be potent therapeutic agents. [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]

An efficient and environmental protocol for the synthesis of 3‐aryl‐2H‐benzo[b][1,4]oxazin‐2‐ones under mild benign conditions has been developed. This facile one‐pot approach to 3‐aryl‐2H‐benzo[b][1,4]oxazin‐2‐ones from commercially available benzoxazoles and α‐keto acids which only promoted by DIPEA. The protocol exhibits a wide range of applicability in terms of benzoxazoles and α‐keto acids. Notably, the 2‐aryl benzothiazoles can be produced under the similar reaction conditions. [ABSTRACT FROM AUTHOR]

Triphenylamine (TPA)‐based Schiff base chemosensors ((E)‐2‐((4‐(diphenylamino)benzylidene)amino)phenol [TPA‐AP], (E)‐5‐(diphenylamino)‐2‐(((2‐hydroxyphenyl)imino)methyl)phenol [HTPA‐AP], and (E)‐5‐(diphenylamino)‐2‐((phenylimino)methyl)phenol [HTPA‐A]) were synthesized and explored the role of metal chelating hydroxyl functionality position for heavy metal ion sensing. TPA‐AP and HTPA‐AP showed Cu2+ ion‐induced chemical transformation and produced oxazole derivatives with turn‐on fluorescence. In contrast, HTPA‐A exhibited metal chelation‐induced turn‐on fluorescence for Zn2+ ion. The reactive chemical sensing of TPA‐AP and HTPA‐AP led to high selectivity of Cu2+, and other ions did not show any interference. The concentration‐dependent studies of Cu2+ and Zn2+ indicated the limit of detection (LOD) up to 6.07 × 10−7 and 4.6 × 10−7 M, respectively. Further, Cr3+, Fe3+, and Fe2+ coordination with TPA‐AP and HTPA‐AP exhibited visible color change from colorless to yellow. However, the yellow color was disappeared and becomes colorless due to imine hydrolysis. Interestingly, all three metal ions showed different rate of hydrolysis and color disappearance. TPA‐AP with Fe3+ exhibited fast hydrolysis and immediate color change whereas Fe2+ and Cr3+ required longer time. But HTPA‐AP and HTPA‐A produced stable complexes with Cr3+, Fe2+, and Sn2+ and Fe3+ alone showed hydrolysis. Thus, the present studies provide structural insight for designing reactive fluorescence and colorimetric Schiff base chemosensor for heavy metal ions. [ABSTRACT FROM AUTHOR]

This work describes a novel iron‐catalysed approach for the synthesis of aryl‐substituted benzimidazoles and benzoxazoles. The methodology employs reductive carbonylation using readily available aryl iodides and aryl amines as precursors, with carbon monoxide serving as the efficient carbonyl source. The reaction proceeds under mild conditions with the addition of hydrosilanes and bases. Notably, aryl aldehydes are generated in situ from the aryl iodides, which subsequently react with o‐phenylenediamine or 2‐aminophenol to afford the desired products in high yields. The structures of the synthesized benzimidazoles and benzoxazoles were confirmed using 1H and 13C NMR spectroscopy and mass spectrometry. [ABSTRACT FROM AUTHOR]

A copper‐catalyzed one‐pot synthesis of substituted bis(benzoxazole)amine, N‐benzoxazole(benzoimidazole)amine, and N‐benzoxazole(benzothiazole)amine is described via intramolecular cyclization of iodophenol and 2‐amino benzimidazoles(thiazoles)(oxazoles)‐trichloroacetonitrile adduct under ultrasound irradiation in MeCN with good yields. The use of simple and readily available starting materials, no column chromatography, mild copper‐catalytic reaction conditions, good yields (74–84 %), applying the sonochemical methodology and short reaction times are remarkable specifications of this protocol. All the compounds synthesized in this design are new and their identities have been confirmed using IR, NMR, CHN and mass spectrometry techniques. [ABSTRACT FROM AUTHOR]

A mild and convenient method for the arylation of benzoxazoles with benzoyl chlorides is reported. This facile protocol used only N,N‐diisopropylethylamine (DIPEA) as an additive. Under the optimal reaction conditions, a wide range of benzoxazoles and benzoyl chlorides were tolerated. With this strategy, benzothiazoles and benzoyl chlorides also reacted well to afford the desired product 2‐aryl benzothiazoles in moderate yields. [ABSTRACT FROM AUTHOR]

Ruthenium(II) polypyridyl complexes continue to raise increasing interest for the encouraging results in several biomedical areas. Considering their vast chemical‐physical repertoire, in particular the possibility to switch from the sensitization of reactive oxygen species (ROS) to ROS‐scavenging abilities by tuning the nature of their ligands, it is therefore surprising that their potential as antioxidants has not been largely investigated so far. Herein, we explored the antioxidant behaviour of the novel ruthenium compound [Ru(dbpy)(2,3‐DAN)Cl]PF6 (Ru1), featuring a benzoxazole derivative (dpby=2,6‐bis(4‐methyl‐2‐benzoxazolyl)pyridine) and the non‐innocent 2,3‐diamminonaftalene (2,3‐DAN) ligand, along with the reference tpy‐containing analogue [Ru(tpy)(2,3‐DAN)Cl]PF6 (Ru2) (tpy=2,2':6',2"‐terpyridine). Following the synthesis and the electrochemical characterization, chemical antioxidant assays highlighted the beneficial role of dpby for the ROS‐scavenging properties of Ru1. These data have been corroborated by the highest protective effect of Ru1 against the oxidative stress induced in SH‐SY5Y human neuroblastoma, which exerts pro‐survival and anti‐inflammatory actions. The results herein reported highlight the potential of Ru1 as pharmacological tool in neurodegenerative diseases and specially prove that the antioxidant properties of such compounds are likely the result of a non‐trivial synergetic action involving the bioactive ligands in their chemical architectures. [ABSTRACT FROM AUTHOR]

N‐heterocyclic compounds are important molecular scaffolds in the search for new drugs, since most drugs contain heterocyclic moieties in their molecular structure, and some of these classes of heterocycles are able to provide ligands for two or more biological targets. Ketene dithioacetals are important building blocks in organic synthesis and are widely used in the synthesis of N‐heterocyclic compounds. In this work, we used double vinylic substitution reactions on ketene dithioacetals to synthesize a small library of heterocyclic derivatives and evaluated their cytotoxic activity in breast and ovarian cancer cells, identifying two benzoxazoles with good potency and selectivity. In silico predictions indicate that the two most active derivatives exhibit physicochemical properties within the range of drug‐like compounds and showed potential to interact with HDAC8 and ERK1 cancer‐related targets. [ABSTRACT FROM AUTHOR]

The impact of the polymeric matrix on the photophysical characteristics of monomeric dyes responsive to excited‐state intramolecular proton transfer (ESIPT) was investigated through UV–Vis absorption as well as steady‐state and time‐resolved emission spectroscopies. For this purpose, two benzoxazole monomers (M1 and M2) with acryloyl groups at different positions in their molecular structures were employed to facilitate covalent bonding within a styrene chain. Our findings reveal significant variations in their excited‐state properties due to the proximity of the acryloyl groups, which affects the energy barrier of the ESIPT reaction, the emission wavelength, and the balance between the normal and tautomeric forms. The experimental results were corroborated through theoretical investigations at the DFT/TDDFT level, specifically using the B3LYP‐D3/def2‐TZVP methodology. Three notable observations emerged: donor/acceptor groups at the meta/para positions induced electron distribution changes, causing red‐shifted emission for M2; in the polymer film, particularly in PM1, intramolecular hydrogen bond deactivation favored N* emission over T* emission; and the zwitterionic character of the T* species. This study underscores the advantages of functionalization in polymers, which can lead to colorless films and prevalent N* or T* emission, and contributes valuable insights into molecular design strategies for tailoring the photophysical properties of polymeric materials. [ABSTRACT FROM AUTHOR]

Development of multifunctional organic materials is an area of intense research interest in organic materials chemistry. This study reports the synthesis, crystal structure elucidation and investigation of multiple properties of E-3-pyridylvinyl benzoxazole (3-PVBO) and its methylated analogue, 3-MPVBO. With Z′ = 2, 3-PVBO belongs to a rare class of crystals for which Z′ > 1. Upon methylation, fascinating material properties were observed. [3-MPVBO]I exhibited strong emission spectra and readily available redox states. It exhibited stronger emission at 474 nm, with a larger Stokes shift of 8900 cm−1, than the emission of 3-PVBO at 386 nm, with a Stokes shift of 5450 cm−1. Upon exposure to UV light, crystals of 3-PVBO underwent a solid-state photodimerization reaction in a head-to-tail fashion (HT), leading to the formation of the HT-rctt isomer of the dimer, i.e., 1,3-bis(benzoxazole)-2,4-bis(3-pyridyl)cyclobutane (PBOCB). Herein, the crystal structure, solid-state photoreactivity, and multiple material properties, e.g., photophysical and electrochemical properties, are presented. [ABSTRACT FROM AUTHOR]

AbstractFe3O4@propyl-semicarbazide-salicyl aldehyde-Cu (Fe3O4@sal-Cu) nanocatalyst was synthesized and characterized by several methods including XRD, SEM, EDX, VSM and FT-IR analyses. The Fe3O4@sal-Cu has been used as an efficient recyclable magnetic catalyst for the preparation of benzimidazoles. The catalyst was conveniently separated from the reaction mixture by an external magnet, and could be reused without any considerable change in catalytic activity. [ABSTRACT FROM AUTHOR]

2‐(2‐methoxyphenyl)benzoxazole (MBO) displays similar photophysical properties to 2‐(2‐hydroxyphenyl)benzoxazole (HBO), but it lacks the large Stokes shifts necessary for fluorescence microscopy applications. In this paper, we report the 5‐substitution of MBO with aryl groups to produce 2‐(4‐methoxy‐[1,1'‐biphenyl]‐3‐yl)benzoxazoles (MBBOs) with large Stokes shifts. The synthesis of MBBOs 6–15 was accomplished in moderate to good yields by microwave‐assisted Sonogashira cross couplings. Crystal structures for compounds 6–9 and 15 are provided. MBBOs 6–10, 12, and 14 displayed considerably blue‐shifted absorption maxima and slight bathochromic shifts of their fluorescence maxima relative to the unsubstituted MBO. [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]

Two new homologous series of mesogenic compounds, alkanoic acid 4-{[4-(6-chloro-benzooxazol-2-yl)-phenylimino]-methyl}-3-hydroxy-phenyl ester (3a-c) and alkcanoic acid 4-(6-chloro-benzooxazol-2-yl)-3-hydroxy-phenyl ester (5a-b) incorporating benzoxazole heterocyclic have been prepared and FT-IR, NMR, and MS spectrometry have been used to study the molecular structures. The mesogenic behaviour was examined using POM, DSC, and PXRD (variable temperature) techniques. To evaluate its impact on thermal behaviour and mesomorphic properties, the imine linking group of derivatives was modified and investigated. Enantiotropic SmA is observed by the members of Series-I, while those of series-II show monotropic SmA mesomorphism. These compounds were also examined for their absorption and fluorescent properties. The absorption and photoluminescence spectra of compounds 3a-c occurred at 345 nm and 410 nm, whereas in the case of 5a-b occurred at 325 nm and 370 nm respectively. The GAUSSIAN-09 programme has been utilised to perform DFT calculations at B3LYP level for the purpose of obtaining the stable electronic structures of 3a and 5a. [ABSTRACT FROM AUTHOR]

Benzoxazoles and benzothiazoles are a class of aromatic heterocyclic compounds having similar ring structures, in which a benzene ring is fused to the 4 and 5 positions of the 1,3-oxazole and 1,3-thiazole rings respectively. They constitute an interesting class of organic compounds due to their powerful and significant biological, agrochemical, pharmaceutical and physicochemical activities. Indeed, benzoxazole and benzothiazole derivatives possess a wide range of applications, such as: anticancer, anti-inflammatory, antioxidant, anticonvulsant, antitubercular, antifungal, pesticidal, anticorrosive, complexing properties and so on. The synthesis of benzoxazole and benzothiazole derivatives has attracted much attention from several researchers across the world and numerous synthetic methods have been developed to access these compounds over the past decades. In this review, we present new and recent synthetic strategies, as well as some biological properties of benzoxazole and benzothiazole derivatives. [ABSTRACT FROM AUTHOR]

An unprecedented silver‐mediated intramolecular oxy‐argentation of 3‐amidoaryne precursors that quickly generates a heteroarylsilver species is developed. AgF acts as both a stoichiometric fluoride source and a reagent for the formation of a benzoxazolylsilver intermediate via aryne generation. Pd‐catalyzed coupling reactions of (hetero)aryl iodides with a silver species, generated in situ, allow for the synthesis of various C7‐arylated benzoxazoles. As a result, an aryl group is selectively introduced into the meta‐position of 3‐amidobenzyne precursors. Mechanistic studies have indicated the presence of a benzoxazolylsilver intermediate and revealed that the reaction proceeds via an intramolecular oxy‐argentation process, which is initiated by a direct fluoride attack on the silyl group. [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]

Trinuclear metallacyclic oxidovanadium(V) complexes, [{VO(L3+2R)}3] (1–3) with asymmetric multidentate linking ligands (H3L3+2R: R = H, Me, Br), were synthesized. The molecular structure of 1 is characterized as a tripod structure, with each V(V) ion coordinated by ONO-atoms from a tridentate Schiff base site and ON-atoms from a bidentate benzoxazole site of two respective H3L3+2H ligands. The intramolecular V⋯V distances range from 8.0683 to 8.1791 Å. Complex 4 is a mononuclear dioxidovanadium(V) complex, (Et3NH)[VO2(HL3+2H)]. Cyclic voltammograms of 1−3 in DMF revealed redox couples attributed to three single-electron transfer processes. [ABSTRACT FROM AUTHOR]

The work presented in the manuscript describes a simple strategy for transforming thermally activated delayed fluorescent organic light‐emitting diodes (TADF OLEDs) compound 10‐(dibenzo[a,c]phenazin‐11‐yl)‐10H‐phenoxazine (DPZ‐PXZ) into type I photosensitizer 10‐(dibenzo[a,c]phenazin‐11‐yl)‐10H‐phenothiazine (DPZ‐PHZ) by strategically introducing sulfur atom in the photosensitizing core. The synthesized compound DPZ‐PHZ exhibits aggregation‐induced enhancement (AIE) and through‐space charge transfer (TSCT) characteristics and generates red emissive assemblies in mixed aqueous media. The original compound DPZ‐PXZ exhibits well‐separated HOMO and LUMO levels and is reported to have highly efficient reverse intersystem crossing (RISC). In comparison, the incorporation of sulfur atom in the phenothiazine donor regulates the electronic communication between donor and acceptor units and promotes the intersystem crossing (ISC) in DPZ‐PHZ molecules. Interestingly, compound DPZ‐PHZ exhibits rapid activation of aerial oxygen for instant generation of superoxide radical anion. Backed by excellent type I photosensitizing activity, DPZ‐PHZ assemblies have high catalytic potential for the synthesis of benzimidazoles, benzothiazoles and quinazolines derivatives under mild reaction conditions. The work presented in the manuscript provides an insight into the combination of heavy atom approach and TSCT for achieving adequate electronic communication between donor and acceptor units, balanced RISC/ISC, and stabilized‐charge separated state for the development of efficient type I photosensitizing assemblies. [ABSTRACT FROM AUTHOR]

A series of novel carboxamide compounds containing benzoxazole motif was synthesized through multiple steps, including electrophilic substitution, cyclization, reduction and amide formation. These processes utilized ortho-aminophenol and heptafluoro-2-iodopropane as starting materials. The structures of these compounds (4a–4r) were characterized by 1H NMR, 13C NMR, and HRMS. Bioassay results revealed that most of these compounds exhibited significant insecticidal activity against Mythimna separata at 500 mg/L. Among them, compound 6-chloro-N-(4-methoxy-3-(6-(perfluoropropan-2-yl)benzo[d]oxazol-2-yl)phenyl)-N-methylnicotinamide (4r) possessed the highest activity, even at 4 mg/L. Molecular docking predicted the binding modes of 4r. These novel carboxamide compounds containing benzoxazole motifs offer valuable insights for designing insecticidal compounds targeting GABA receptors, aiming to control lepidopteran pests effectively. [ABSTRACT FROM AUTHOR]

A new approach for synthesizing triazole rings through the application of laccases, copper containing oxidoreductase enzymes is outlined. A series of benzothiazoles and benzimidazoles-functionalized alkynes were initially synthesized utilizing a biocatalysis laccase-based approach. The resultant alkynes were further treated with aryl azides in a 1,3-dipolar cycloaddition reaction facilitated by laccase enzymes to obtain 1,2,3-triazole-fused benzothiazoles and benzimidazoles. [ABSTRACT FROM AUTHOR]

This article provides a comprehensive overview of recent advances in the synthesis of C-glycosides, which are compounds that contain a carbon-carbon bond between the sugar moiety and another group. The text discusses various synthetic routes and reactions, such as the carbon-Ferrier rearrangement, that have been used to synthesize C-glycosides. These compounds have potential applications in the development of therapeutics and have shown promising antimicrobial and antiviral activity. The article also highlights the potential applications of C-glycosides in medicinal chemistry and the synthesis of natural products. [Extracted from the article]

We report the substrate and conditions switchable synthetic methods for the preparation of benzothiazoles, benzothiazines and benzothiazepines based on the reactions of o‐aminothiophenol with hetareno[e]pyrrole‐2,3‐diones, 1H‐pyrrole‐2,3‐diones fused at the [e]‐side to heterocycles. The series of novel five‐, six‐ and seven‐membered N,S‐heterocycles were prepared in fair to excellent yields. The reported reactions proceeded under mild, catalyst‐free conditions, and the products were isolated by simple workup procedures. [ABSTRACT FROM AUTHOR]

Benzoxazole‐linked covalent organic frameworks (BO−COFs), despite their exceptional chemical stability, are still in their infancy. This is primarily because the current prevalent methods require the use of special ortho‐hydroxyl‐substituted aromatic amines as monomers. Herein, we report an innovative strategy to access BO−COFs directly from imine‐linked COFs (Im−COFs) without pre‐embedded OH groups, using a two‐step sequential oxidation/cyclization process. The two‐step process included the oxidation of Im−COFs into amide‐linked COFs, followed by a copper‐catalyzed oxidative cyclization. Five representative BO−COFs were synthesized with retained crystallinity and high oxidization efficiency, offering the potential to convert a significant portion of Im−COFs into BO−COFs. The structural advantages of the newly designed BO−COFs were demonstrated through their application to photocatalytic organic transformations. [ABSTRACT FROM AUTHOR]

In this study, we synthesized sulfamic acid-functionalized Fe3O4 nanoparticles (Fe3O4@EDA-SO3H) as an effective nanomagnetic solid acid catalyst. This magnetically recoverable catalyst was well characterized by FT-IR, XRD, TGA, VSM, SEM, EDX, TEM, and CHN techniques. The prepared catalyst exhibited high efficiency in the synthesis of quinoxaline, benzothiazole, and benzoxazole derivatives such as 3,2-diphenylquinoxaline (97%), 2-phenyl-benzothiazole (97%), and 2-(4-chlorophenyl)benzoxazole (95%) via simple and mild conditions. The catalyst can be readily separated from the reaction medium by employing an external magnet and reused several times without significant loss of its catalytic activity. [ABSTRACT FROM AUTHOR]

A facile oxidative cyclization of β -ketothioamides for the simultaneous formation of a compound library similar to natural product benzothiazole derivatives has been developed. The oxidative cyclization of β -ketothioamides resulted in the simultaneous formation of four classes of previously unknown benzothiazole derivatives. This chemistry's versatility adds a valuable component to the methodology for obtaining benzothiazole derivatives. We have developed a facile oxidative cyclization of β -ketothioamides for the simultaneous formation of a compound library similar to natural product benzothiazole derivatives, which are important structural motifs that are prevalent in both natural and designed compounds and display interesting biological and physical properties. (Image credit: M. Cui.) [ABSTRACT FROM AUTHOR]

Dyes derived from benzothiazoles are an important class of heterocycles which have remarkable photophysical properties. New photoluminescent 2-phenylbenzothiazole derivatives containing different functional groups were synthesized in high yields and used for silylated derivatives synthesis. The new photoactive compounds were fully characterized and their photophysical properties were investigated. The absorption and fluorescence spectra of the benzothiazoles and their silylated derivatives were evaluated in a series of organic solvents. The results showed that the benzothiazoles present absorption in the ultraviolet range and emission in the blue region with moderate quantum yields and large Stokes shift. The solvatochromism of these compounds was investigated by using Lippert and ET(30) Dimroth-Reichardt empirical solvent polarity scales. The dipole moments obtained by Bakshiev and Kawaski-Chamma-Viallet equations revealed that the excited states were more polar than the ground states. [ABSTRACT FROM AUTHOR]

Benzoxazole is an attractive scaffold in medicinal chemistry due to its diverse biological applications. From 2016 to 2023, a plethora of benzoxazole derivatives have been synthesized and evaluated for their pharmacological activities but a review on this topic was found lacking. This review thus aims to fill the gap and discusses the pharmacological activities of the synthesized derivatives, emphasizing their interactions with key biological targets implicated in diseases such as cancer, diabetes, pain, inflammation, and cardiovascular disorders. Relevant works were selected mainly from databases such as PubMed and Google Scholar to offer a comprehensive overview of derivatives with promising bioactivities. The limitations pertinent to some derivatives, such as poor in vitro or in vivo activities, were highlighted, while their prospects in drug discovery was discussed. [ABSTRACT FROM AUTHOR]

A convenient and efficient method for the synthesis of benzimidazoles, and benzothiazoles have been developed using recyclable magnetite polydopamine-supported copper nanoparticles (Fe3O4@PDA/CuCl2) under green and mild conditions. This catalytic system enables the one-pot synthesis of benzazoles by employing available, and easy to-handle aldehydes and o-phenylenediamine/o-aminothiophenol. Utilizing sustainable and mild conditions, a variety of functionalized benzazoles has been prepared in nearly quantitative yields (79–97%) within 5–30 min at 40 °C. The method offers advantages such as high yield, short reaction time, use of air as oxidant, ease of workup, avoiding toxic organic solvents, and a simple workup protocol. The catalyst could be recycled and reused up to five times without any loss of significant catalytic activity. The catalyst's great effectiveness can be seen in the fact that the TON reaches 2633–3233 and the TOF reaches 5266–38,800 h−1. [ABSTRACT FROM AUTHOR]

The secondary sulfonamide derivatives containing benzothiazole scaffold (1–10) were synthesized to determine their inhibition properties on two physiologically essential human carbonic anhydrases isoforms (hCAs, EC, 4.2.1.1), hCA I, and hCA II. The inhibitory effects of the compounds on hCA I and hCA II isoenzymes were investigated by comparing their IC50 and Ki values. The Ki values of compounds (1–10) against hCA I and hCA II are in the range of 0.052 ± 0.022–0.971 ± 0.280 and 0.025 ± 0.010–0.682 ± 0.335, respectively. Some of these inhibited the enzyme more effectively than the standard drug, acetazolamide. In particular, compounds 5 and 4 were found to be most effective on hCA I and hCA II. [ABSTRACT FROM AUTHOR]

Sulfonamides are widely used in the treatment of many diseases due to their biological and pharmacological activities. In this paper, we prepared Cu(II) complex immobilized on the surface of magnetic Fe3O4 nanoparticles functionalized with 2-Pyridine Benzoimidazole ligand [MNPs@PBI-CuBr2] and its catalytic activity in the synthesis of N-aryl sulfonamides containing benzoxazole scaffolds through one-pot three-component reaction of 2-aminobenzoazoles, sulfonyl chloride and aryl iodides under ecofriendly conditions. The structure of the as-prepared MNPs@PBI-CuBr2 nanomaterial was well characterized by a number of spectroscopic techniques such as FTIR, SEM, EDX, TEM, XRD, TGA, VSM, MAP, XPS and ICP-OES. The MNPs@PBI-CuBr2 nanocatalyst was simply separated by magnetic separation and reused for seven times with constant activity. The TEM, XRD pattern and ICP-OES spectroscopy of catalyst after recycling were studied and the results were similar to before of utilization. [ABSTRACT FROM AUTHOR]

Sustainability is one of the hot topics of today's research, in particular when it comes to energy‐storage systems such as batteries. Redox‐active molecules implemented in organic batteries represent a promising alternative to lithium‐ion batteries, which partially rely on non‐sustainable heavy metal salts. As an alternative, we propose benzothiazole, ‐oxazole and ‐imidazole derivatives as redox‐active moieties for polymers in organic (radical) batteries. The target molecules were identified by a combination of theoretical and experimental approaches for the investigation of new organic active materials. Herein, we present the synthesis, electrochemical characterization and theoretical investigation of the proposed molecules, which can later be introduced into a polymer backbone and used in organic polymer batteries. [ABSTRACT FROM AUTHOR]

The article discusses the use of benzoxazole and benzothiazole as directing groups for palladium- and ruthenium-catalyzed C-H arylation reactions. The authors explore different reaction conditions and catalysts to achieve selective arylation of these compounds. They also investigate the effects of substituents on the aryl unit and the benzoxazole/benzothiazole moiety. The document provides valuable information for researchers interested in the synthesis and functionalization of heterocyclic compounds. Additionally, the document includes experimental procedures and characterization data for specific compounds synthesized using the methods discussed. [Extracted from the article]

The document is a contents list for the journal CrystEngComm. It includes a range of papers on topics such as the design and understanding of solid-state and crystalline materials. The journal is published by The Royal Society of Chemistry, a leading chemistry community. The document also mentions other journals in the field of energy research and sustainable energy technologies. [Extracted from the article]

This study presents the utilization of 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO) radical-immobilized metal–organic frameworks (MOFs) for the oxidative cyclization of aldehydes and aminophenols, leading to the heterogeneous synthesis of 2-substituted benzoxazole molecules. The TEMPO-immobilized MOFs are successfully employed in one-pot sequential aerobic oxidation and oxidative cyclization reactions that enable the synthesis of 2-phenyl benzoxazoles from readily available benzyl alcohols and ortho-aminophenol precursors. The modified MOFs exhibit exceptional reactivity towards benzoxazole synthesis, demonstrating a wide range of substrate compatibilities and efficient performance under simple reaction conditions. Through the implementation of a mixed-ligand approach, precise control over the molar fraction and density of TEMPO radicals is achieved. Among the synthesized catalysts with radical density control, UiO-68-(TEMPO)1.0, which features the complete immobilization of TEMPO, displays the highest catalytic efficiency in the oxidative cyclization process. This enhanced performance can be attributed to the dual involvement of TEMPO species in the proposed reaction mechanism for oxidative cyclization. Notably, the MOF-TEMPO catalyst can be recycled up to five times without any loss of catalytic activity or crystallinity. This research is significant because the sequential approach proposed in this study bridges the TEMPO-catalyzed aerobic oxidation of alcohols and TEMPO-catalyzed oxidative cyclization of aldehydes with aminophenols under the same TEMPO catalyst and O2 atmosphere. [ABSTRACT FROM AUTHOR]

The use of ligand combination approach in the Pd catalyzed direct C−H arylation of benzothiazole and benzoxazole is demonstrated. The combination of two ligands phenanthroline monohydrate (Phen.H2O) and triphenylphosphine (PPh3) with Pd‐catalyst have offered the best catalytic properties in the C−H bond arylation reactions than either of two ligands employed separately in the reactions. This protocol exhibits a wide substrate scope affording C2 arylated benzothiazole and benzoxazole derivatives in excellent yields. Mechanistic studies including kinetic isotope effect (KIE), H/D exchange and competition experiments show that the C−H bond activation of benzothiazole and benzoxazole is very facile under reaction conditions. Furthermore, different mechanistic pathways originated from the catalytically active species such as Pd(η2‐dba)L (dba=dibenzylidene acetone) and Pd(PPh3)2 were investigated using computational methods. The computational results suggest that the generation of catalytically active species from Pd2(dba)3 is endoergic process and Phen ligand can initiate this step. On the other hand, the presence of PPh3 could be crucial for the oxidative addition of aryl halides which is the rate‐determining step of the reaction. [ABSTRACT FROM AUTHOR]

Several novel approaches to target Bcl-2 proteins and apoptotic pathways have been identified in recent years for the treatment of different types of cancer including colorectal cancer. However, no effective treatments were yet developed for colorectal cancer. Twenty two novel benzoxazole and thiazole−based compounds were designed, synthesized, and evaluated as potential Bcl-2 inhibitors with anti−proliferative activity. Compounds 8g, 12e and 13d showed good to moderate anti−proliferative activity against most of the NCI 60 cell line panel with mean growth inhibition percent of 45.13, 42.29 and 29.25%, respectively. They showed the greatest cell growth inhibition percent to HCT-116 cell line with the values of 68.0, 59.11 and 43.44%, respectively. The aforementioned compounds were furtherly investigated for their effect on HCT-116 cell cycle, and they showed increase in the total apoptosis with 17, 22, and 5%, respectively. Also, the apoptotic effect of compounds 8g, 12e and 13d, were tested by their effect on altering caspase-3 expression level in HCT-116 human cell line. The three compounds showed an increase in the caspase-3 levels by 6, 8 and 3 folds, respectively in comparison with the same untreated ones. Moreover, they were evaluated for their in–vitro Bcl-2 inhibitory activity and they showed percent inhibition of 60.2, 69.2 and 50.0%, respectively. Finally, the most potent compounds 8g and 12e showed 3.864 and 2.834 folds increase in Bax level compared to the control respectively. On the other hand, Bcl-2 was down−regulated to 0.31 and 0.415 folds compared to the control. The induction of apoptosis through increase in caspase 3 expression and down−regulation of Bcl-2 is the suggested mechanism of action. [ABSTRACT FROM AUTHOR]

Synthesis of 2-aryl substituted benzoxazoles, benzothiazoles, and quinoxalinones via decarboxylative coupling of α-keto acids with 2-aminophenol, 2-aminothiophenol, and OPD (o-phenylenediamine), using K2CO3 as a base in water at room temperature, and as well as solvent-free grinding and the synthesis of benzoxazinones from the reaction of α-keto acids with 2-aminophenol at 60 °C have been reported. Both the protocols afforded a wide range of desired products with excellent functional group tolerance in yields of 87-99%. The major advantages of these approaches are catalyst-free protocol, short reaction times, straightforward workup, and chromatographyfree processing of the products. Additionally, to test the translational demand of this methodology, the synthesis of 2-(3,5-dichlorophenyl)- 6-methylbenzo[d]oxazole was carried out which is a key structure of tafamidis, a commercially available drug. [ABSTRACT FROM AUTHOR]

A series of benzamide derivatives containing quinoxaline and benzoxazole fragments were synthesized and characterized by 1H NMR and mass spectra. The antibacterial activity of the synthesized derivatives was tested in vitro against gram-positive and gram-negative bacterial strains using an agar well diffusion assay. The molecular docking study showed good docking scores between –9.85 and –7.8 kcal/mol against DNA gyrase (PDB ID: 4KTN). [ABSTRACT FROM AUTHOR]

In this study, new 1,3-thiazolidin-4-one derivatives containing arylmethylene groups in the 5-position were obtained from 6-(trifluoromethoxy)-1,3-benzothiazol-2-amine (riluzole). Synthesized compounds were characterized by spectral data and elemental analysis. In vitro, cytotoxic activities of the synthesized molecules were evaluated against the human lung cancer (A549) and human prostate cancer (PC-3) cell lines. Compounds were also tested on mouse embryonic fibroblast cells (NIH/3T3) to determine selectivity. Ten target compounds 3-12 were also screened for their COX-1 and COX-2 inhibitory activities. Of these compounds, 4 showed the highest COX-2 inhibition at 10 μM. Molecular docking calculations were performed to understand the binding interactions of compounds with COX-1 and COX-2 proteins. In silico studies of the tested compounds represented important binding modes that may be responsible for their anti-cancer activity via selective inhibition of the COX-2 enzyme. ADMET predictions were conducted to assess the drug-like properties of the novel compounds. [ABSTRACT FROM AUTHOR]

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A novel metal-free and environment-friendly approach for synthesizing biologically important moieties, benzothiazoles and benzimidazoles, under visible light irradiation using photocatalyst Eosin Y, ethanol:water as a green solvent and atmospheric air as an oxidant has been developed. Using an organic dye, Eosin Y, provided a mild and economical catalytic system to synthesize a series of benzothiazoles and benzimidazoles in good to excellent yields. Besides, the photocatalytic system does not require an additional oxidant, which is good for the environment. This method has several advantages, including the absence of metals, low cost, environmental friendliness, green solvent, non-toxicity, ease of handling, and renewable energy sources such as visible light. [ABSTRACT FROM AUTHOR]

Synthesis of benzoxazoles via amide formation from amino phenols and α‐diazoesters using dicobalt octacarbonyl as a solid CO source is reported. Our methodology provides a strategy for synthesizing substituted benzoxazoles with methylene linker between the benzoxazole and aromatic ring systems. Substrates with different substituents were employed to produce corresponding benzoxazoles. The synthesized compounds were characterized by using standard spectroscopic and analytical techniques including single crystal XRD studies. [ABSTRACT FROM AUTHOR]

Driven by the growing threat of cancer, many research efforts are directed at developing new chemotherapeutic agents, where the central role is played by transition metal complexes. The proper ligand design serves as a key factor to unlock the anticancer potential of a particular metal center. Following a recent trend, we have prepared unsymmetrical pincer ligands that combine benzothiazole and thiocarbamate donor groups. These compounds are shown to readily undergo direct cyclopalladation, affording the target S,C,N-type Pd(II) pincer complexes both in solution and in the absence of a solvent. The solid-phase strategy provided the complexes in an efficient and ecologically friendly manner. The resulting palladacycles are fully characterized using nuclear magnetic resonance (NMR) and infrared (IR) spectroscopy and, in one case, by single-crystal X-ray diffraction (XRD). The solvent-free reactions are additionally analyzed by powder XRD. The pincer complexes exhibit remarkable cytotoxicity against several solid and blood cancer cell lines, including human colorectal carcinoma (HCT116), breast cancer (MCF7), prostate adenocarcinoma (PC3), chronic myelogenous leukemia (K562), multiple plasmacytoma (AMO1), and acute lymphoblastic leukemia (H9), with the dimethylamino-substituted derivative being particularly effective. The latter also induced an appreciable level of apoptosis in both parental and doxorubicin-resistant cells K562 and K562/iS9, vindicating the high anticancer potential of this type of palladacycles. [ABSTRACT FROM AUTHOR]

An iridium complex based on the unsymmetrical pyrenyl‐thiophene‐benzothiazole ligand was synthesized, and the iridium complex was supported on reduced graphene oxide successfully. The developed iridium catalyst PTB‐Ir@rGO was characterized through SEM, TEM, XPS, EDS. Meanwhile, we found that this heterogeneous iridium catalyst had high catalytic activity in N‐alkylation of benzamide with alcohols via borrowing hydrogen strategy. Moreover, several control reactions and preliminary mechanism explorations were carried out to study this transformation. Finally, the recycling experiment showed that the catalyst could be reused at least five times without a significant decrease in catalytic activity. [ABSTRACT FROM AUTHOR]

The article represents a translation of Section 6.2 of the monograph authored by A.S. Burlov, V.G. Vlasenko, D.A. Garnovskiy, A.I. Uraev, E.I. Maltsev, D.A. Lypenko, and A.V. Vannikov, Electroluminescent Organic Light-Emitting Diodes Based on Metal Coordination Compounds, Rostov-on-Don: Yuzhn. Fed. Univ., 2015; ISBN 978-5-9275-1469-4 (see Additional Information), dedicated to reviewing the photoluminescence and electroluminescence properties of metal complexes based on (Zn, Cd, Al, Sc, Be, B) with azoles (2-(2-hydroxyphenyl)benzothiazoles, 2-(2-hydroxyphenyl)benzoxazoles, 2-(2-hydroxyphenyl)benzimidazoles, azaindoles, oxadiazoles, and their derivatives) as ligands. Modifying such ligands by introducing electron-donating substituents into various positions of the phenyl fragments leads to significant changes in their electroluminescence characteristics. Metal complex compounds with ligands of this type are widely used for creating OLED devices emitting white light. [ABSTRACT FROM AUTHOR]

In the present study a series of ethyl 4-(substituted)-2-methyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylate and ethyl 4-(substituted)-8-methoxy-2-methyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3-carboxylate have been synthesized and evaluated for their preliminary antibacterial, antifungal, antimycobacterial, antioxidant and antimalarial activity. Among all the synthesized derivatives some of the compounds exists good biological activity which is similar to that of standard drugs. These facts make the compounds interesting candidates for further evaluation of their efficacy in the treatment microbial, tubercular and malarial disease. [ABSTRACT FROM AUTHOR]