Azo Derivatives Research Articles

Discovery of novel azo pyrimidinone derivatives as B-cell lymphoma-2 inhibitors with potential antineoplastic activity: Synthesis, characterization, in-silico, and in-vitro studies

In the present investigation, novel azo compounds containing pyrimidinone moiety incorporated with different heterocycles were synthesized and characterized using spectroscopic techniques including FT-IR, 1H-NMR, 13C-NMR, and elemental analysis. These azo derivatives were assessed in- silico to determine how well they could inhibit the antiapoptotic B-cell lymphoma-2 (Bcl-2) protein while providing information about their pharmacokinetic characteristics. Our results elucidated that the majority of these new compounds demonstrated moderate to strong binding energies against Bcl-2 target protein comparable to that of venetoclax FDA-approved Bcl-2 inhibitor. Compound 4 showed the top-ranked binding energy followed by compound 5 and compound 3 with values equal to -11.65, -9.53, and -7.82 kcal/mol respectively, while compounds 6 and 7 showed moderate binding energies compared with venetoclax drug that give binding energy equal to -6.95 kcal/mol Furthermore, the in-vitro investigations observed that compounds 4, 5 and 3 demonstrated superior anticancer efficacy against HepG2 and MCF-7 compared to venetoclax drug that gives IC50 equal to 5.10±0.54 and 4.17±0.8 μM respectively. Moreover, all newly synthesized compounds had no cytotoxic impact on WI-38 normal cells contrary to venetoclax drug (26.72±0.94 μM) which was confirmed also through ADMES drug-likeness scores study. Additionally, compounds 4, 5, and 3 revealed an efficient antioxidant scavenging capacity towards DPPH free radicals while compounds 6 and 7 showed a weak scavenging effect compared with standard L. ascorbic acid. Ultimately, the newly synthesized pyrimidinone compounds 4, 5, and 3 that were examined showed encouraging apoptotic and antiproliferative properties. Further, in upcoming clinical studies, the newly synthesized pyrimidinone compounds may prove to be effective anticancer medicines.

Innovative Photoprotection Strategy: Development of 2-(Benzoxazol-2-Yl)[(2-Hydroxynaphthyl)Diazenyl] Phenol Derivatives for Comprehensive Absorption of UVB, UVA, and Blue Light.

Overexposure to blue light due to the excessive use of electronic devices has been implicated in premature skin aging and eye damage, among other injuries to health. This study aimed to synthesize two azo derivatives of the 2-(amino-2'-hydroxyphenyl) benzoxazole and explore their potential as UV and blue light filters, proposing a new spectral profile. The synthesis of the heterocyclic compounds involved condensation reactions and diazotation. The derivatives 2-(benzoxazol-2-yl)-5-[(2-hydroxynaphthyl)diazenyl]phenol and 2-(benzoxazol-2-yl)-4-[(2-hydroxynaphthyl)diazenyl]phenol were synthesized with a yield greater than 70%. Solubility was evaluated in seven different solvents. The maximum absorption wavelengths (λmax) were determined using UV-Vis scanning spectrophotometry in the range of 200-600 nm. Photostability was assessed using a solar simulator and the Sun protection factor (SPF) was determined using invitro methodology. Cytotoxicity was evaluated using the MTT assay in V79 cells. These compounds were able to absorb UVA, UVB, and blue light, with λmax ranging from 300 to 500 nm and demonstrated photostability after 3 h of exposure to solar simulator with an SPF higher than 45. The compounds exhibited solubility in all lipophilic solvents tested. Regarding cytotoxicity, IC50 values were comparable to other filters. These findings indicate that both compounds hold promise as potential organic filters.

Synthesis and Antitumour Activity of Hybrid Compounds Based on 4-Aminophenylarsonic Acid and Spatially Hindered Phenols.

One of the main modern approaches to the creation of effective drugs is the design of new biologically active substances containing two or more pharmacophore groups in their structure. In recent years, there have been many publications on the synthesis and study of biological activity, including antitumour activity, of new organo-arsenic compounds. It is known that spatially hindered phenols can also have antitumor activity, so the synthesis and study of hybrid compounds based on organo-arsenic compounds and spatially hindered phenols is a relevant area of research. In this work, the modification of 4-aminophenylarsonic acid with 3,5-di-tert-butyl-4-hydroxybenzylacetate was carried out. In contrast to a similar transformation of 2-aminophenylarsonic acid, in this case it was possible to obtain both mono- and di-benzyl derivatives of the acid. Using the Zandmeyer method, the oxime isatin containing an arsonic acid fragment in the fifth position of the heterocycle was synthesised. Azo derivatives containing fragments of para-aminophenylarsonic acid and sterically hindered phenols were obtained. 4-((3,5-Di-tert-butyl-2-hydroxyphenyl)diazenyl)phenylarsonic acid was isolated in pure form. At the same time, it was found that the reaction of the diazonium azo salt of 4-aminophenylarsonic acid with 2-hydroxymethyl-4-tert-butylphenol proceeds in two directions. In addition to the classical diazotisation reaction at the 6-position of 2-hydroxymethyl-4-tert-butylphenol, a diazotisation accompanied by a dehydroxymethylation process occurs. The obtained compounds showed cytotoxic activity against human tumor cell lines M-HeLa (cervical epithelioid carcinoma) and HuTu 80 (duodenal adenocarcinoma cells). The most promising is the sodium salt of 4-((3,5-di-tert-butyl-2-hydroxyphenyl)diazenyl)phenylarsonic acid, which is superior to Tamoxifen and 5-fluorouracil in terms of selectivity index towards M-HeLa and HuTu 80 cells.

Synthesis, biological evaluation, molecular docking analyses, and ADMET study of azo derivatives containing 1-naphthol against MβL-producing S. maltophilia

Stenotrophomonas maltophilia is a model organism exhibiting intrinsic antibiotic resistance, primarily due to its production of Mβ-lactamase enzymes that inactivate β-lactam antibiotics. This study aims to synthesize an azo derivative containing an oxazepine ring as a potential inhibitor of Mβ-lactamase. The molecular docking results revealed that the binding energies of the Mβ-lactamases ranged from − 5.95 to − 6.09 kcal/mol, indicating favourable interactions with the synthesized compounds. Two compounds were prepared: the first via aldol condensation of (A1) with p-hydroxybenzaldehyde to form (K1) and the second through Azo-Schiff base formation from 3,5-dimethylaniline, resulting in (L2) and (L18). Characterization of these compounds was conducted via FT-IR, CHN, 1H NMR, and 13C NMR spectroscopy. Antimicrobial activity was assessed through minimum inhibitory concentration (MIC) and minimum bacterial concentration (MBC) tests, which yielded values ranging from 1.19 ± 1 to 0.02 µg/mL and from 1.12 ± 1 to > 0.04 µg/mL, respectively. Notably, the MBC/MIC ratios indicated that L2 and L18 exhibited significant bactericidal activity. In silico analysis via MOE 2015 software allowed us to determine the binding poses and energies of the synthesized inhibitors against Mβ-lactamase (PDB ID: 6UAF). The most stable conformation from the docking results was selected for further evaluation. Compared with standard ceftazidime, the synthesized compounds significantly inhibited Mβ-lactamase activity. Additionally, ADMET analysis indicated favourable pharmacokinetic profiles and low toxicity, suggesting promising oral drug-like properties for the synthesized molecules.

Unveiling the therapeutic potential of azopyridine derivatives for trypsin inhibition: a DFT and In-Vitro approach

Heterocyclic azo derivatives have emerged as promising scaffolds for drug development. This study focused on the synthesis, computational analysis, and biological evaluation of a series of azopyridine derivatives (1a, 1d, 1 g, 1 h, 1 m, 1p, and 1s) as potential trypsin inhibitors. Density Functional Theory calculations indicated that derivative 1 h exhibited the lowest HOMO-LUMO energy gap 3.167 eV and was characterised as a soft molecule, suggesting strong binding capabilities. Molecular docking studies confirmed that 1 h binds favourably to the active site of trypsin with a glide score of −6.581 kcal/mol and binding energy of −29.95 kcal/mol. Along with docking studies, the stability of the trypsin-1 h complex was further analyzed using molecular dynamic simulations at 200 ns. The results showed that the ligand molecule 1 h bound strongly at the active site of trypsin. In-vitro enzyme assays determined the IC50 value of the molecule as 100 µM, demonstrating enhanced potency. These results indicate that AzPy derivatives, particularly 1 h, hold considerable promise as therapeutic agents for inflammatory disorders and cancer, paving the way for further exploration in drug development and targeted therapies. Further research is warranted to explore 1h’s efficacy, safety, and structure-activity relationships. Highlights: DFT studies were used to classify molecules based on their softness and hardness. Molecular docking, simulation, and in-vitro studies have identified potential anti-trypsin activity of candidate molecules. Experimental and computational calculations were in close agreement.

A Simple Dispersive Liquid-Liquid Microextraction for the Determination of Copper II in the Water Samples of the Halfaya Oil Field in Maysan

Background: Copper, an important trace element for life on Earth, is crucial to many metabolic processes. This includes its role in the production and breakdown of nucleic acids and the metabolism of proteins, lipids, and carbohydrates. Objective: We aim to integrate DLLME with a spectrophotometric method to establish a novel approach for quantifying trace amounts of copper in water samples. Methods: In this study, a new ligand known as a 2-(4 aminophenol) benzimidazole azo derivative was successfully synthesized. This ligand was created by converting 2-(4-aminophenyl) benzimidazole into a diazonium salt and coupling it with 8-hydroxyquinoline in an alkaline environment. The resulting product was a brown azo dye, which served as the ligand for detecting copper (II) in aqueous samples. Results: To analyze copper (II) in both pure and aqueous samples, we developed and validated micro-extraction techniques combined with UV-Vis measurement. Specifically, we used the DLLME (dispersive liquid-liquid microextraction) method to separate, enrich, and assess copper (II) in both its pure form and in aqueous samples. UV-Vis spectroscopy at a wavelength of 503 nm was used for this purpose. We considered several variables during the experiment, including the type and volume of the dispersive solvent, the extraction solvents, the temperature, the reaction duration, and the centrifuging time. By optimizing these conditions, we achieved linear procedures within the concentration range of (1.0–25.0) and (2.0–25.0) μg/mL for spectroscopy and DLLME methods, respectively. For the spectroscopic and DLLME approaches, the coefficient of determination (R2) was found to be 0.9963 and 0.9979 for the spectrophotometric and DLLME methods, respectively. The limit of detection (LOD) for copper (II) was found to be 0.23 and 0.04 μg/mL, respectively. Moreover, the recovery of the target analyte in aqueous samples was found to be between 95.6% and 101% for the spectroscopy method and between 102.4% and 108.2% for the DLLME method. Conclusions: These results demonstrate the effectiveness and accuracy of both methods in analyzing copper (II) in aqueous samples.

Synthesis, Characterization, and Optical Properties of Novel Heterocyclic Azo Dyes and Evaluation of Their Antioxidant Activity as an Active Sunscreen Agent

AbstractWe synthesized some novel isoxazole azo derivatives using conventional methods and studied their linear, non‐linear optical properties and antioxidant activity. UV‐Vis spectroscopy revealed absorption bands ranging from 310–470 nm for the obtained compounds. Compounds 3 c and 3 b, for example, showed a large redshift and solvatochromic behavior. NLO analysis results show that compounds exhibit a greater NLO response than the magnitude of urea done by the DFT method. The electrochemical properties of compounds are studied using cyclic voltammetry and results are used for calculation of HOMO and LUMO experimentally. The antioxidant activity of the synthesized azo dyes displayed that 3 c has excellent antioxidant activity with the highest percentage (71.54605 %) of radical inhibition as compared to reference standard Vit‐C. Molecular docking analysis shows that compounds have a strong binding affinity in the range of −7.0 to −4.6 kcal/mol compared to Vit‐C, which has a binding affinity of −3.6 kcal/mol. The sun protection factor performance was determined by UV‐Vis spectroscopy, and results show that compounds are most effective, exhibit a remarkable SPF value, and offer superior sun protection by absorbing UV rays.

Preparation, in vitro and in silico antioxidant and antibacterial studies of 4-aminoacetanilide azo derivatives

A new series of new 4-aminoacetanilide azo derivatives 1–13 were successfully synthesised via a diazo coupling reaction and gave a good to excellent yield of 73 %–93 %. The antioxidant capabilities of the series 1–13 screened through 2,2′-diphenyl-1-picrylhydrazyl (DPPH) assay and ferric reducing antioxidant power (FRAP) assay showed promising data of 12.6–199.4 ppm and 12.65–210.9 mg/ml Trolox equivalent, respectively. The findings supported by in silico docking analysis targeted Heme oxygenase-1 (HO-1) evidenced by a binding score of – 7.2 to – 8.2 kcal/mol outperforming the standard, ascorbic acid scoring only – 5.7 kcal/mol. Among all, compound 11 displayed the highest antioxidant potential with IC25 of 12.6 ppm against DPPH assay and 210.9 mg/ml Trolox for FRAP assay believed owing to the presence of methoxy group at ortho position in the phenolic compound that effectively lowered the ionisation potential and high up energy of highest occupied molecular orbital (HOMO). Nevertheless, the antibacterial potential of the series screened through the Kirby-Bauer disc diffusion method against Escherichia coli and Staphylococcus aureus showed no antibacterial activity postulated due to the presence of amide and acetyl group restricted the ability of the compound to form an interaction with the protein receptor of bacteria tested. This study provided new insight into the development of dual-functional drugs for non-communicable diseases and antimicrobial resistance.

A review of the synthesis and application of azo dyes and metal complexes for emerging antimicrobial therapies

Antimicrobial resistance presents a formidable challenge to contemporary medicine, necessitating innovative therapeutic solutions. Azo dyes and their metal complexes have emerged as promising candidates due to their notable antimicrobial properties. This review comprehensively examines the synthesis and application of azo dyes and metal complexes for emerging antimicrobial therapies. Through various synthetic strategies and metallation, the chemical structure of azo derivatives allows for modifications that enhance their antimicrobial efficacy, making them promising candidates for pharmaceutical development against microbial infections. The study provides a comprehensive understanding of the mechanisms of antimicrobial action, including DNA intercalation, enzyme inhibition, membrane disruption, and reactive oxygen species generation. The role of metal ions is particularly significant, enhancing structural stability, reactivity, and the ability to target microbial enzymes effectively. Chelation effects, such as reduced polarity and increased lipophilicity, facilitate the penetration of microbial cell membranes and the disruption of enzyme activity. The review highlights novel azo-metal complexes’ significant antifungal and antibacterial activities, particularly their efficacy against pathogens such as Mycobacterium tuberculosis. The importance of structure-activity relationships is detailed, showing how specific functional groups and metal ions influence antimicrobial efficacy. Additionally, their potential sensing ability to detect and identify microorganisms highlights the multifaceted role of azo dye derivatives in infection management.

Synthesis, Characterization, Molecular docking, Antibacterial Activity, Antioxidant and Anticancer of New 1,2,4-Triazole Derivative

A novel 1,2,4-triazole-5-thiol derivative was designed through a series of reactions. Firstly, Azo derivative 1 was synthesized by a general method with two steps, a diazotization reaction in an acidic medium, and a coupling reaction in basic conditions. Secondly, Azo-carboxylic acid 1 reacted with SOCl2 to produce acid chloride derivative 2. Then carbothiamide derivative 3 was synthesized through substitution reaction by reacting 2 with 4-phenyl thiosemicarbazide in pyridine. In the next step, carbothiamide 3 was reacted with sodium hydroxide solution to afford target triazole derivative 4. The structures of all synthesized derivatives were confirmed by techniques (1H, 13C NMR, IR). Moreover, the triazole derivative 4 was evaluated for its biological activity as an anticancer, antioxidant, and antibacterial. The results presented that compound 4 has moderate antibacterial activity and a high free radical scavenging effect (IC50 30.2 μg/mL) compared to vitamin C (IC50 21 μg/mL). The anticancer activity results presented that compound 4 has a toxic effect on a colon cancer cell line CaCo-2. The potential effect of compound 4 on the 5lqf protein was examined in silico studies.

Synthesis, DFT investigations, antibacterial activity, and SAR-study of novel thiophene-coumarin hybrids

A series of thiophene-coumarin hybrids (3, 5, 7, and 9) has been produced from the reaction of various thiocarbamoyl compounds with 3-bromoacetylcoumarin. The DFT/B3LYP approach revealed that the synthesized hybrids have a non-planar configuration. The explored hybrids exhibited close HOMO-LUMO energies, whereas the carboxamide analogues 7 and 9 presented lower energies than azo derivatives 3 and 5. The increase in antibiotic resistance presents a significant danger to public health, necessitating the development of novel antimicrobial medications. The antibacterial properties of the synthesized thiophene-coumarin hybrids were evaluated against representative microorganisms, including Gram-positive and Gram-negative bacteria, along with fungi, and they exhibited diverse antibacterial activity. The hybrids 7a and 5b showed strong activity (IC50 < 37 and <68 µg/mL) against the Gram-positive bacteria S. aureus and S. epidermidis, respectively. While hybrid 9a exhibited significant antifungal efficacy against C. albicans (IC50 <184 µg/mL), surpassing Flucytosine. Also, the targeting hybrids exhibited different levels of effectiveness in inhibiting DNA gyrase. Hybrid 9a showed the highest potency, followed closely by 7a (IC50 5.19±0.12 and 6.05±0.23 µM, respectively) against Novobiocin. Moreover, the docking study demonstrates the interaction between the newly synthesized hybrids and the 4URO protein, a critical target for therapeutic intervention. Additionally, the Swiss ADME analysis of hybrids 5a and 5b has been displayed because of their exceptional combination of physicochemical features and bioavailability ratings.

Verification of the Inverse Scale Effect Hypothesis on Viscosity and Diffusion by Azo-Amino Acid Schiff Base Copper Complexes

Microdroplets generated in microfluidic devices are attracting attention as a new chemical reaction field and are expected to improve reactivity. One of the effects of microscaling is that the ratio of the force that acts on the diffusion and movement of substances to gravity is different from that of ordinary solvents. Recently, we proposed a hypothesis for determining reaction acceleration through micro-miniaturization: If a reaction is inhibited by setting the volume and viscosity of the solution to conditions that are unfavorable to the reaction on a normal scale, that reaction can be promoted in microfluidics. Therefore, for the purpose of this verification, (1) we used an amino acid Schiff base copper(II) complex with an azobenzene group to demonstrate the polarization-induced orientation in a polymer film (the redirection that is mechanically maintained in a soft matter matrix). Numerical data on optical anisotropy parameters were reported. (2) When the reaction is confirmed to be promoted in laminar flow in a microfluidic device and its azo derivative, a copper(II) complex is used to increase the solvent viscosity or diffusion during synthesis on a normally large scale. We will obtain and discuss data on the investigation of changing the solvent volume as a region. The range of experimental conditions for volume and viscosity did not lead to an improvement in synthetic yield, nor did (3) the comparison of solvents and viscosity for single-crystal growth of amino acid Schiff base copper(II) complexes having azobenzene groups. A solvent whose viscosity was measured was used, but microcrystals were obtained using the diffusion method.

Synthesis, characterization of new electrochemical activated sulfadiazine azo dyes and its theoretical studies with LFPs, antioxidant application

The present study describes the optoelectronic, LFPs visualizations and DPPH scavenging activity using sulfadiazine azo dyes. The resulting azo product was obtained through a diazo-coupling reaction of sulfadiazine with different coupling compounds under ambient experimental conditions and confirmed through IR, 1H NMR, 13C NMR, LC-MS, and UV–Vis spectroscopic techniques. The computational studies were investigated using the B3LYP/6–311 + g(d,p) basis set in the Gaussian 09 W program at the gaseous phase. Electrochemical behavior was analyzed for synthesized compounds and fine redox peaks at increasing scan rates in the CH instrument. In addition, experimental calculations of HOMO-LUMO energies were conducted using electrochemical redox on set potentials and compared with theoretical values. Further, a latent fingerprint application for azo derivatives was developed using the powder dusting method, resulting in clear visuals of level I whorl and level Ⅱ bifurcation and eye ridge finger marks registered in normal and UV light. Compound 3b exhibited excellent DPPH scavenging activity (IC50 = 172.04 µg). In silico docking simulations were done for the synthesized azo compounds using the antioxidant enzyme, human peroxiredoxin5 (1HD2) as a receptor. In silico study of the designed azo dye compounds exhibit enormous binding energy (-6.6, −6.5, −6.4 kcl/mol) in comparison with the standard drug (-5.7 kcl/mol). docking results were closely linked to the experimental DPPH scavenging activity.

Green Synthesizing and Corrosion Inhibition Characteristics of Azo Compounds on Carbon Steel under Sweet Conditions: Experimental and Theoretical Approaches.

The deterioration of carbon steel in saline solutions enriched with carbon dioxide represents a significant challenge within the oil and gas industry. So, this study focuses on the design and structural analysis of four azo derivatives: 4-(2-quinolinylazo)-catechol (AZN-1), 4-(4-phenoxyphenylazo)-1-naphthol (AZN-2), 4-(4-pyridylazo)-1-naphthol (AZN-3), and 4-(2-pyridylazo)-1-naphthol (AZN-4), and their first application as effective corrosion inhibitors for carbon steel in a carbon dioxide saturated 3.5% sodium chloride solution. Spectroscopic methods were used to characterize the structural configurations of these compounds. The corrosion protection properties of these compounds on carbon steel in a carbon dioxide saturated 3.5% sodium chloride solution (under sweet conditions) were investigated using Tafel polarization (PDP), electrochemical impedance spectroscopy (EIS), and field emission-scanning electron microscopy (FE-SEM) studies. The results indicate that the inhibition efficiency increases as the concentration of the inhibitors increases. There is a notable agreement between the results obtained from the PDP and EIS measurements, supporting the findings. Moreover, the results displayed that these compounds had significant corrosion protection capabilities at low concentrations, ranging from 91.0 to 98.3% at an additive concentration of 5 × 10-4 M. The PDP profiles showed that these compounds acted as mixed inhibitors, and their adsorption behavior followed the Langmuir isotherm model. Besides, EIS results corroborate the adsorption of AZN compounds through a reduction in double-layer capacitance (Cdl) alongside an augmentation in polarization resistance (Rp) after the addition of AZN compounds into the corrosive solution. Field emission scanning electron microscopy (FE-SEM) and Fourier-transform infrared spectroscopy (FTIR) analysis confirmed the formation of a protective layer on the surface of carbon steel when these inhibitors were applied. In addition, computational calculations and Monte Carlo simulations were performed to support the experimental observations, gain insights into the adsorption properties, and elucidate the corrosion inhibition mechanisms of these compounds.

New Azo Derivative of β-Diketones and Its Cu(II), Co(II) Complexes: Synthesis, Theoretical Study and Biological Activity.

The paper is focused on biological activity and theoretical study of the structure and properties of a new azo derivative of β-diketones and its complexes with some metals. The aim of our work was to study the structure and properties of the newly synthesized compound as well as to theoretically determine the possibility of complex formation with the Cu(II) or Co(II) ions. A compound with the same substituents R1=R2=CH3 was chosen for the study. A synthesized azo compound based on 4-amino antipyrine and its complexes with Cu(II), Co(II) in solution and solid phase is reported. The structures of these compounds have been testified by X-ray, IR and NMR spectroscopy. The combined experimental and theoretical approach was used. To study the structure and properties of the synthesized compound, as well as its possible complex formation with the Cu(II), quantum-chemical calculations were carried out the 6-31G basis set and the electron density functional theory (DFT) method. These 3-(1-phenyl-2,3-dimethyl-pyrazolone-5) azopentadione-2,4 (PDPA) with Cu(II) and Co(II) complexes had effective inhibition against butyrylcholinesterase and acetylcholinesterase. IC50 values were found as 19.03, 3.64 μM for AChE and 28.47, 8.01 μM for BChE, respectively. Cholinesterase inhibitors work to slow down the acetylcholine's deterioration.

Ultrasensitive SERS quantitative detection of antioxidants via diazo derivatization reaction and deep learning for signal fluctuation mitigation

Synthetic antioxidants serve as essential protectors against oxidation and deterioration of edible oils, however, prudent evaluation is necessary regarding potential health risks associated with excessive intake. The direct adsorption of antioxidants onto conventional surface-enhanced Raman scattering (SERS) substrates is challenging due to the presence of phenolic hydroxyl groups in their molecular structures, resulting in weak Raman scattering signals and rendering direct SERS detection difficult. In this study, a diazo derivatization reaction was employed to enhance SERS signals by converting antioxidant molecules into azo derivatives, enabling the amplification of the weak Raman scattering signals through the strong vibrational modes induced by the N = N double bond. The resulting diazo derivatives were characterized using UV–visible absorption and infrared spectroscopy, confirming the occurrence of diazo derivatization of the antioxidants. The proposed method successfully achieved the rapid detection of three commonly used synthetic antioxidants, namely butylated hydroxyanisole (BHA), tert-butylhydroquinone (TBHQ), and propyl gallate (PG) on interfacial self-assembled gold nanoparticles. Furthermore, rapid predictions of BHA, PG, and TBHQ within the concentration range of 1 × 10−6 to 2 × 10−3 mol/L were achieved by integrating a convolutional neural network model. The predictive range of this model surpassed the traditional quantitative method of manually selecting characteristic peaks, with linear coefficients (R2) of 0.9992, 0.9997, and 0.9997, respectively. The recovery of antioxidants in real soybean oil samples ranged from 73.0 % to 126.4 %. Based on diazo derivatization, the proposed SERS method eliminates the need for complex substrates and enables the analysis and determination of synthetic antioxidants in edible oils within 20 min, providing a convenient analytical approach for quality control in the food industry.

Azo derivatives of monoterpenes as anti-Helicobacter pylori agents: from synthesis to structure-based target investigation.

Helicobacter pylori (Hp) infection affects nearly half of the global population. Current therapeutic options include the administration of a combination of antibiotics and proton pump inhibitors, although antimicrobial resistance rise remains a big concern. Phenolic monoterpenes, e.g., eugenol, vanillin, carvacrol, and thymol, have always attracted researchers for their multifaced biological activities and the possibility to be easily derivatized. Thereby, herein we present the functionalization of such compounds through the conventional aryl diazotization reaction, generating a series of mono- and bis-azo derivatives (1-28). Also, to continue previous studies, we investigated the role of the free phenolic moiety of thymol with eight compounds (29-36). The compounds were tested against four Hp strains including three clinical isolates, finding some potent and selective inhibitors of bacterial growth. Thus, the representative compounds underwent in vitro cytotoxicity evaluation on two normal cell lines and putative target investigation by performing a structure-based approach based on docking calculations on some of the most studied pharmacological targets for Hp, e.g., urease, β-hydroxyacyl-acyl carrier protein dehydratase, glucose 6-phosphate dehydrogenase, and inosine 5'-monophosphate dehydrogenase.

New Azo Derivatives of Thiacalix[4]arene: Synthesis, Structure and Complexation with Dyes

New Azo Derivatives of Thiacalix[4]arene: Synthesis, Structure and Complexation with Dyes

Red-light-responsive cucurbit[8]uril based host–guest interaction enabling the construction of a photoswitchable supramolecular polymeric hydrogel

A red/blue light induced photoswitchable host–guest system based on CB[8] and water soluble low cytotoxic azo derivatives is constructed, enabling the fabrication of supramolecular polymeric hydrogel with red light-induced gel–sol transformation.

Recent Advances in Efficient Photocatalytic Degradation Approaches for Azo Dyes

In recent decades, the textile industry has contributed to continuous pollution in the environment. Synthetic dyes which are commonly found in waste water are azo, sulfur, anthraquinone, triphenylmethyl, indigoid, and phthalocyanine derivatives. These pollutants block the light penetration in water bodies and prevent photosynthesis activity, thereby affecting aquatic life. As an environmental crisis, several technologies have been explored to control pollution. Among all the techniques, the photocatalysis process is considered as a green, simple, and economical process. To improve the photocatalytic activity, researchers worldwide have investigated various photocatalysts such as metal oxides, metal ferrites, and heterostructured nanocomposites. The major goal of this review article is to propose a high-performing, cost-effective hybrid photocatalyst reported to date for prospective azo dye pollutant remediation. This review article also aimed to highlight the challenges and uncertainties associated with dye degradation in the photocatalytic process.