Aromatic Derivatives Research Articles

Discovery of Unique Bis-Substituted Aromatic Amide Derivatives as Novel Highly Potent Antibiotics for Combating Methicillin-Resistant Staphylococcus aureus (MRSA).

Due to the increasing antibiotic resistance, developing novel antimicrobials to fight infections caused by resistant bacteria is imperative. Herein, a series of novel bis-substituted aromatic amides were designed and synthesized through modifying the hit compound 1, and their antimicrobial activities were evaluated. Among them, compound 4t, as the most potent lead, exhibited excellent antimicrobial activities against Gram-positive bacteria, including clinical methicillin-resistant Staphylococcus aureus (MRSA) isolates, while keeping weak hemolytic and mammalian cytotoxic activities. Furthermore, compound 4t displayed rapid bactericidal capabilities, low tendency to produce resistance, and favorable capacities to destroy bacterial biofilms. Further explorations indicated that compound 4t induces bacterial death by binding to cardiolipin (CL) on the bacterial membrane, disrupting the cell membrane, and facilitating the accumulation of reactive oxygen species (ROS). Additionally, compound 4t showed remarkable anti-MRSA activity in vivo, demonstrating compound 4t could be developed as a potential candidate to combat MRSA infections.

NIR Emissive Functional Nanoparticles Promote Precise Pancreatic Cancer Therapy by Co‐Targeting Mutant p53 and Oncogenic KRAS

AbstractPancreatic ductal adenocarcinoma (PDAC) presents a formidable global health challenge. Targeting genetic aberrations, particularly KRAS and TP53 mutations, remains a critical challenge in PDAC treatment. Herein, it is demonstrated for the first time that electron‐rich aromatic pyrrole derivatives can be transformed into red‐to‐near‐infrared emissive radical cations in an acidic buffer, efficiently targeting mitochondria and triggering mutant p53 (mutp53) degradation. Leveraging the positive charge characteristic of radical cations (P6•+), a bifunctional nanoparticle is successfully engineered by combining P6•+ with KRAS siRNA. P6@siKRAS simultaneously induces mutp53 degradation and the oncogenic KRAS downregulation, thereby abrogating gain‐of‐function effects by mutp53 and inhibiting downstream signaling pathways regulated by KRAS, leading to significant suppression of tumor growth, invasion, and drug resistance. Consequently, P6@siKRAS demonstrates remarkable therapeutic efficacy in both the p53‐KRAS‐double‐mutated pancreatic cancer model and the LSL‐KrasG12D/+; LSL‐Trp53R172H/+; Pdx‐1‐Cre (KPC) mice model. Moreover, the down‐regulation of mutp53 and KRAS by P6@siKRAS not only inhibits tumor growth but also substantially remodels the tumor microenvironment, recruiting and boosting the infiltration of anti‐tumor immune cells, thereby augmenting the anti‐tumor immune response. This study showcases the development of mutp53‐degrading functional gene carriers, offering a promising and innovative therapeutic strategy for tackling p53‐KRAS‐double‐mutated pancreatic cancer.

Imparting aromaticity to 2-pyridone derivatives by O-alkylation resulted in new competitive and non-competitive PIM-1 kinase inhibitors with caspase-activated apoptosis

New aromatic O-alkyl pyridine derivatives were designed and synthesised as Proviral Integration Moloney (PIM)-1 kinase inhibitors. 4c and 4f showed potent in vitro anticancer activity against NFS-60, HepG-2, PC-3, and Caco-2 cell lines and low toxicity against normal human lung fibroblast Wi-38 cell line. Moreover, 4c and 4f induced apoptosis in the four tested cancer cell lines with high percentage. In addition, 4c and 4f significantly induced caspase 3/7 activation in HepG-2 cell line. Furthermore, 4c and 4f showed potent PIM-1 kinase inhibitory activity with IC50 = 0.110, 0.095 µM, respectively. Kinetic studies indicated that 4c and 4f were both competitive and non-competitive inhibitors for PIM-1 kinase enzyme. In addition, in silico prediction of physiochemical properties, pharmacokinetic profile, ligand efficiency, ligand lipophilic efficiency, and induced fit docking studies were consistent with the biological and kinetic studies, and predicted that 4c and 4f could act as PIM-1 kinase competitive non-adenosine triphosphate (ATP) mimetics with drug like properties.

Removal of organic amino derivatives from wastewater by using fluorescent nitrogen-doped GQDs under visible light and fluorescence application under ultra violet light

Photocatalysis is one of the most popular organic waste degradation treatments because it can result in the total decomposition of organic pollutants under visible light illumination. Here, we present a metal-free visible-light active catalyst for the effective decomposition of organic aromatic amino derivatives Methylene blue (MB) and Rhodamine B (RB) as model-contaminated dye molecules. Through a one-pot hydrothermal process, blue colour emissive nitrogen-doped graphene quantum dots (N-GQDs) were synthesized from urea and malic acid. The physicochemical characteristic techniques were used to analyze the surface morphology, elemental analysis, surface functional groups, absorption, emission, and band gap of prepared N-GQDs. The effective light absorption properties, transfer of electrons, separation of photoinduced charge carriers, and excellent stability with a band gap of 2.69 eV of synthesized N-GQDs have enabled the degradation of Rh B and MB up to 90 % and 86 % respectively, within 120 min of visible light irradiation. Based on extensive active species trapping experiments, a probable photocatalytic dye degradation mechanism is proposed. These N-GQDs can also be used to make fluorescent ink for imaging and security purposes.

Removal of Aromatic Amino-derivatives from Aqueous Solutions Using Polymeric Supports Functionalized with Aminophosphonated/aminoacid-phosphonated Groups

Aromatic amines are the significant compounds used as intermediates in the organic synthesis, for obtaining such as azo dyes, antioxidants, fuel additives, corrosion inhibitors, pesticides, antiseptic agents, poultry medicine, and pharmaceutical synthesis. However, the presence of aromatic amines in water, even at very low concentrations, is extremely harmful to aquatic life and human health. Pollution of natural waters by aromatic amines is a serious environmental concern. The aim of this work was to obtain new adsorbents for use in the removal of aromatic amines from aqueous solutions. Styrene-15%divinylbenzene copolymers grafted with aminophosphonate groups (code: AP-S15%DVB) and amino acid-phosphonate groups (code: AM-S15%DVB) were used for the removal of pollutants such as: aniline, 2-methyl-aniline and 4-methyl-aniline. The adsorption capacity and the adsorption kinetic using the pseudo-first order and pseudo-second order equations were examined. From a kinetic point of view, it was established that the adsorption of the studied amino derivatives on the used adsorbents took place according to the pseudo-second order model. It was found that the adsorption rate constant increased with the increase of temperature, so the speed of the adsorption process increased. The obtained results confirm that the polymer adsorbents studied can be successfully used for the removal of aromatic amino derivatives from aqueous solutions for the purpose of wastewater treatment.

Visible-light-driven photocatalytic carboxylation to aromatic carboxylic acids with CO2.

(Hetero)aromatic carboxylic acids and their derivatives attract attention due to their role in the synthesis of several biologically active molecules, active pharmaceutical ingredients, polymers, etc. Carbon dioxide (CO2) is a prime C1 source for the synthesis of aromatic carboxylic acids because of its nontoxicity, nonflammability, abundance and renewability. Owing to the thermodynamic and chemical inertness of CO2, traditional carboxylation to aromatic carboxylic acids with CO2 is always performed under harsh reaction conditions or using stoichiometric metallic reductants. Visible-light-driven carboxylation with CO2 provides an environmentally benign, mild, and high-efficiency route for the production of aromatic carboxylic acids. This review comprehensively introduces the visible-light-driven preparation of aromatic carboxylic acids through a visible-light-driven oxidative addition and reductive elimination mechanism, binding of aryl (radical) anions which are produced by photoinduced electron transfer (PET) to CO2, binding of carbon dioxide anion radicals (CO2˙-) which are formed by PET to aryl compounds, radical coupling between CO2˙- and aryl radicals, and other mechanisms. Finally, this review provides a summary and the future work direction. This article offers a theoretical guidance for efficient synthesis of aromatic carboxylic acids via photocatalysis.

Construction of polyimide structures containing iron(ii) clathrochelate intercalators: promising materials for CO2 gas uptake and salient adsorbents of iodine from gaseous and liquid phases

Three novel imide-iron(ii) clathrochelate copolymers (ACP1–3) were synthesized via a microwave-assisted polycondensation reaction employing a specially designed diamine iron(ii) clathrochelate surrogate with various aromatic dianhydride derivatives.

Design, Synthesis, Characterization and Modification of Novel Aromatic Compounds with Poly Vinyl Alcohol

New aromatic compounds were prepared by reacting 5,5and#39;-methylene di-anthranilic acid with 4,4and#39;-(diazene-1,2-diyl) dibenzoyl chloride by the well-known classical methods. To prepare compounds to contain an amide, ester, and azo groups as a bonding bridge between them. The synthesized was characterized by CHN, FT-IR, 1HNMR, and 13CNMR spectra. Then, they were reacted with polyvinyl alcohol PVA polymer using cold-warm esterification to prepare new graft polymers. The structures of the composites were determined by FT-IR. Graft polymerization of PVA with new aromatic compounds was a way to prepare important polymeric materials with original physicochemical properties for use in new industrial applications. By testing aromatic derivatives the swelling results of the newly prepared graft polymers were very good, ranging from 3-665%, with a life span of a quarter of an hour to three days. While DSC analysis showed good temperatures in the range of 23.4-289.2and#176;C for the prepared graft polymers.

Synthesis, in vitro antioxidant, anticancer activity and molecular docking of new thiazole derivatives

Nitrogen and sulfur-containing heterocyclic aromatic derivatives play an enormous and important role in the field of medicine and in synthesis of pharmaceutically active compounds. In this study, a series of new 2-[1-(1,3-diphenyl-1H-pyrazol-4-yl)ethylidene]hydrazinyl)-4-methyl-5-aryldiazinyl)-thiazole derivatives (9a–d) was synthesized by an efficient and convenient method by reacting hydrazonoyl chloride derivatives (4) with carbothioamide derivative (3). The structures of these compounds were elucidated using elemental analyses, spectroscopic analyses (IR, NMR, Mass spectrometer) and computational measurements. Density functional theory (DFT) is performed to get the optimized structures with minimization Energy. The main goal of preparing these compounds is to evaluate their in vitro antioxidant and anticancer activities after studying their molecular docking. The docking was performed on compounds (9a–d) against tyrosine kinase (PDB ID: 2HCK). The results revealed that all docked compounds (9a-d) have a higher binding energy, ranging from −7.56 to −8,89 kcal/mol. compared to the original ligand quercetin, which was −5.92 kcal/mol. Moreover, the results of antioxidant and anticancer activity assay methods demonstrated that the tested derivatives (9a-d) exhibited potent antioxidant and anti-tumor activities against HepG2 cell lines.

Elucidating metal composition–coking relationships and coke formation pathways during gas-phase oxydehydration of glycerol over clay mineral-supported Mo-V-O catalysts

Catalyst deactivation by carbon deposition (coking) remains a major obstacle in many important industrial processes, such as catalytic gas-phase oxydehydration of glycerol. Understanding the chemical nature and development of coke species during the time-on-stream (TOS) of the catalytic solids is therefore crucial for mitigating the extent of coking and in the design of regeneration process of the coked catalysts. In this study, multiple analytical techniques, including SEM, XRD, FTIR, Raman, GC-MS, XPS, and 13C solid-state MAS NMR were employed to gain insights into the coking behavior of acid-activated montmorillonite (HMMT) supported Mo-V-O catalysts with modulated metal ratios, along with soluble and insoluble coke compositions and their evolution over time. Insoluble coke was comprised of polycyclic aromatic compounds with 5 or more fused-benzene rings containing different types of oxygen-bonded groups, such as −OCH3, −COOH, −CHO, and −OH. The major chemical constituents of soluble coke were mononuclear aromatic derivatives (i.e., xylenes, 2,4-di-tert-butylphenol, and 1-hydroxycyclohexyl phenyl ketone) and paraffinic hydrocarbons with 12–18 carbon atoms. The latter coke species is thought to be formed via the deoxygenation of linear oligoglycerols. The insights presented in this study may aid in understanding the carbon deposition process during gas-phase oxydehydration of glycerol for improved design of supported Mo-V-O catalyst materials with high coking resistance.

Synthesis and Decoration of Aromatic Derivatives Nano Platelets by the Electric Method

The present work consists of synthesizing a five-decorated aromatic amine derivatives. The decoration involves aromatic derivatives nano-platelets through an electric process using aromatic amine derivatives such as Sulfamethoxazole, \(2\)-Amino-\(6\)-chloro benzothiole, Trimethoprim, \(2\)-Amino benzoic acid, and \(4\)-Amino phenol. This process occurs in an electric cell containing platinum electrodes with a voltage of \(1.6\) volts, resulting in the production of compound \((R1,R5)\). These compounds were characterized and diagnosed using physical and spectroscopic methods, including infrared spectroscopy (FT-IR), \(X\)-ray diffraction (XRD), electron microscopy (FESEM), atomic force microscopy (AFM), and \(H1\)-NMR.

Fast and efficient processes for oxidation and monitoring of polycyclic aromatic hydrocarbons in environmental matrices

This study proposes a new approach for the efficient photodegradation of polycyclic aromatic hydrocarbons (PAH) and derivatives. PAH removal was achieved in just a few minutes using a microwave photochemical reactor capable of producing a high concentration of •OH (2.3 mmol L−1 h−1). Fluorescence excitation-emission matrix (EEM) spectroscopy coupled to parallel factor analysis (PARAFAC) was used for quantifying two PAH and one alkylated PAH at low concentrations (μg L−1). These results highlight the high potential of the photochemical degradation system coupled to EEM-PARAFAC as an alternative fast, inexpensive, and efficient approach for environmental remediation studies of PAH.

Phylloplane fungus Curvularia dactyloctenicola VJP08 effectively degrades commercially available PS product

Polystyrene (PS), a widely produced plastic with an extended carbon (C–C) backbone that resists microbial attack, is produced in enormous quantities throughout the World. Naturally occurring plasticizers such as plant cuticle and lignocelluloses share similar properties to synthetic plastics such as hydrophobicity, structural complexity, and higher recalcitrance to degradation. In due course of time, phytopathogenic fungi have evolved strategies to overcome these limitations and utilize lignocellulosic waste for their nutrition. The present investigation focuses on the utilization of phylloplane fungus, Curvularia dactyloctenicola VJP08 towards its ability to colonize and degrade commercially available PS lids. The fungus was observed to densely grow onto PS samples over an incubation period of 30 days. The morphological changes showcased extensive fungal growth with mycelial imbrication invading the PS surface for carbon extraction leading to the appearance of cracks and holes in the PS surface. It was further confirmed by EDS analysis which indicated that carbon was extracted from PS for the fungal growth. Further, 3.57% decrease in the weight, 8.8% decrease in the thickness and 2 °C decrease in the glass transition temperature (Tg) confirmed alterations in the structural integrity of PS samples by the fungal action. GC-MS/MS analysis of the treated PS samples also showed significant decrease in the concentration of benzene and associated aromatic derivatives confirming the degradation of PS samples and subsequent utilization of generated by-products by the fungus for growth. Overall, the present study confirmed the degradation and utilization of commercially available PS samples by phylloplane fungus C. dactyloctenicola VJP08. These findings establish a clear cross-assessment of the phylloplane fungi for their prospective use in the development of degradation strategies of synthetic plastics.

The Synthesis of Some Imine Derivatives via Condensation Reactions between Some Aromatic Phenylhydroxylamine Derivatives with Glyoxylic Acid and the Study of their biological activity

This study investigated the condensation reactions between N-(3,4-dimethoxybenzyl)hydroxylamine and N-(4-methylbenzyl)hydroxylamine with glyoxalic acid. The objective was to obtain imine derivatives as the desired target products. FT-IR, 1H-NMR, and 13C-NMR spectroscopic techniques were used to identify the structures of the produced compounds. Different conditions were considered for these reactions and only N-(3,4-dimethoxybenzyl)hydroxylamine could be converted to the desired nitrone. Finally, the antimicrobial efficacy was assessed in terms of its action against the bacteria Escherichia coli (E.coli) as Gram-negative bacteria, Staphylococcus aureus (S.aureus) as Gram-positive bacteria and fungus (Candida albicans). The activity data proved that this nitrone showed significant antimicrobial activity compared to standard drugs.

Synthesis, characterization and hydrolytic degradation studies of aromatic polyphosphazenes derivatives

Synthesis, characterization and hydrolytic degradation studies of aromatic polyphosphazenes derivatives

Nucleotide-based regenerated fiber production using salmon (Oncorhynchus keta) milt waste by solution spinning

The use of nucleic acid-derived fibers has not been developed in contrast to the traditional use of polysaccharide- and protein-based fibers in daily life. Salmon, Oncorhynchus keta, is an abundant fishery resource, and its milt contains a huge amount of DNA. Most of the milt is discarded because it degrades easily and is unsuitable for food consumption. DNA-based fibers are expected to possess functionality and mechanical strength because DNA is a polyanion with a high molecular weight. Here, using DNA extracted from the salmon milt, we produced nucleotide-based fibers. A solution spinning system was applied using ethanol as a coagulant. Adding the salt to the dope solution reduced the solubility of DNA, which was essential for the successful spinning of DNA-based fibers. The obtained fibers became insoluble in water by ultraviolet (UV) exposure. Fibril-like structures were detected on the fracture surface, and humidity influenced the conformational structure. This study focuses on the bulk-scale production of biodegradable DNA-based fibers. Therefore, it can be used not only for clothing and filters but also as a functional material to remove harmful pollutants released into the ocean, such as heavy metal ions and aromatic derivatives.

Increasing the aqueous solubility of N-acyl-substituted amino acid esters using iron(II) ions as inhibitors of viral replication in vitro

New aromatic and heterocyclic derivatives of N-acylated esters of l-amino acids with aromatic carboxylic acids are proposed as antiviral low molecular weight agents. To increase the aqueous solubility of inhibitors that are insoluble in aqueous solutions, the target compounds were used as iron(II) chloride complexes. It was shown that compounds in the form of coordinated ligands are able to suppress the replication of the strain of influenza A virus resistant to adamantane. The presumed target of inhibitor compounds is viroporin M2 in the envelope of the influenza A virus. At the same time, these compounds were found to be inactive in relation to the SARS-CoV-2 coronavirus strain.

Degradation of Azo Dye Solutions by a Nanocrystalline Fe-Based Alloy and the Adsorption of Their By-Products by Cork.

In this study, the efficiency of mechanically alloyed Fe80Si10B10 in degrading basic red 46 azo dye is investigated. Moreover, the influences of different parameters, such as pH and time, on the elimination of the aromatic derivatives obtained as by-products of the fracture of the azo group are also analyzed. After beginning the reduction to the normal conditions of pH (4.6) and temperature, the experimental findings showed a discoloration of 97.87% after 20 min. The structure and morphology of the nanocrystalline Fe80Si10B10 powder were characterized by SEM and XRD before and after use in the degradation process. The XRD patterns of the Fe-Si-B powder after redox reaction suggest that the valent zero Fe of the alloy is the reducing agent. Powdered cork was then used as a biosorbent for the removal of the by-products generated, resulting in increasing removal percentages from pH 7 (26%) to pH 9 (62%) and a contact time of 120 min. The FTIR spectrum of the cork after adsorption shows a shift of the bands, confirming the interaction with the aromatic amines. The present findings show that metallic powders and natural cork perform well together in removing azo dye solutions and their degradation products.

A novel and thermostable phenylalanine dehydrogenase for efficient synthesis of bulky aromatic amino acids and derivatives

Phenylalanine dehydrogenases (PDHs) play an important role in pharmaceutical and fine chemical industries due to their ability to produce primary amines via asymmetrically reductive amination. However, the industrial application of PDHs are often limited by their undesirable stability, narrow substrate specificity, especially for unnatural substrates. Here, a novel PDH from Quasibacillus thermotolerans (QtPDH) was identified by gene mining using BbPDH from Bacillus badius as a probe. QtPDH exhibits prominent thermal stability, specifically a half-life of 23 days at 30 °C and pH 8.5, about 300 times longer than that of BbPDH. QtPDH could catalyze various phenylpyruvate analogues, including ethyl 2-oxo-4-phenylbutyrate and l-phenylglycinol, as well as bulky 3-(naphthalen-1-yl)-2-oxopropanoic acid with a reductive amination specific activity of 1.90 U·mg–1. Catalyzed by QtPDH in couple with BmGDH, efficient production of 2‑chloro-l-phenylalanine was achieved at 1.0 M 3-(2-chlorophenyl)-2-oxopropionic acid with > 99 % conversion, 99 % ee, and space-time yield of 30.46 g·L–1·h–1. Our results suggest that this newly identified QtPDH features high catalytic efficiency and thermostability, and is a promising biocatalyst for the industrial productions of bulky aromatic primary amines.

Anticancer effect of aromatic isoniazid derivatives in human gastric adenocarcinoma cells

Current treatments for stomach cancer are often effective in curing cancer. However, these treatments can also have significant side effects, and they may not be effective in all cases. Hence synthetic compounds exhibit promise as potential agents for cancer treatment. In a previous study, we identified (E)-N′- (2,3,4-trihydroxybenzylidene) isonicotinohydrazide (ITHB4) as a novel antimycobacterial derivative of isoniazid with cytotoxic effects on the MCF-7 breast cancer cell line. This led us to investigate the potential anti-cancer properties of ITHB4 against adenocarcinoma gastric (AGS) cell line. The cytotoxic effect of ITHB4 has been determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay and further confirmed for anticancer properties by means of apoptosis, reactive oxygen species (ROS), nuclear fragmentation, lactate dehydrogenase (LDH), caspases, cytokines and morphological including phenotypic changes of cells assay. The ITHB4 demonstrated a lower IC50 in inhibiting growth of AGS cells at 24 h compared to 48 and 72 h. ITHB4 has also shown no toxicity human immune cells. Treatment of ITHB4 against AGS for 24 h eventually lead to formation of early apoptotic AGS cells, reduced mitochondrial membrane potential, nuclear condensation, and nuclear fragmentation lastly increased in ROS levels together with the release of LDH, and secretion of caspases. The altered cytokine profile in ITHB4 treated AGS hints at the possibility that ITHB4 may possess anti-tumor and anti-inflammatory properties. Our results in this study demonstrate that ITHB4 has almost similar chemotherapeutic properties against gastric adenocarcinoma cells compared to breast cancer cell. This is suggesting that the anticancer capabilities of this compound should be in vivo and clinically assessed.