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"Chemical Communications" is a journal published by The Royal Society of Chemistry, focusing on various topics in the field of chemistry. The latest issue includes articles on organic molecular design for sodium-ion batteries, chemistries on the cell membrane, advancements in flexible biomechanical energy harvesting, and recent developments in cancer therapy using nanomaterials. The journal also features research on terpene synthases, biochar functionalization, CO2 electroreduction, and electron transfer in molecular photocatalysts. [Extracted from the article]

Natural coumarins represent a diverse group of secondary metabolites with a wide range of biological activities. However, their specific molecular targets have remained largely unexplored. Employing chemical proteomics, a comprehensive analysis of the protein targets of the natural coumarin fraxetin has been conducted. Prostaglandin reductase 2 (PTGR2), a key enzyme involved in the final inactivation of prostaglandins, was identified as a primary target of fraxetin. Inhibition of PTGR2 can lead to the accumulation of 15-keto-PGE2, which subsequently activates the Nrf2 signaling pathway and suppresses NF-κB, resulting in notable anti-inflammatory effects. These findings provide novel insights into the molecular targets of fraxetin and other coumarins, which are crucial for fully exploring their therapeutic potential. [ABSTRACT FROM AUTHOR]

The synthesis of biologically active coumarin-based hydrazone derivatives is achieved through a one-pot, three-component reaction of 4-hydroxy-2 H -chromene-2-thiones with aniline derivatives and tert -butyl nitrite under solvent- and catalyst-free conditions in yields of 76–86%. Similarly, the reactions of 4-hydroxydithiocoumarins with aniline derivatives and tert -butyl nitrite under identical conditions provided the corresponding hydrazone products in 79–85% yield through a four-component reaction. It is observed in both cases that the C=S group at the C2 position is converted into a C=O moiety. However, the intermediate products derived from 4-hydroxydithiocoumarin react further with another aniline molecule leading to thioesters. 4-Hydroxy-2 H -chromene-2-thione and 4-hydroxydithiocoumarin exhibit distinct reactivity pathways, resulting in the formation of two different types of product. In addition, quantum chemical analysis of the mechanistic steps show that this reaction is exergonic. This protocol offers broad substrate scope and tolerates various functional groups, leading to high product yields in short reaction times. [ABSTRACT FROM AUTHOR]

The current study is a continuation of our previous investigations into the radical homodimeric reaction mechanism of 3-acetylcoumarin. In the current study, the effects of different substituents on the coumarin ring of 3-acetylcoumarin are investigated both experimentally and theoretically. Several 3-acetylcoumarin derivatives (substituted at C-6, C-7, and C-8) were tested in the optimized reaction conditions under ultrasound irradiation, and biscoumarin species were isolated and characterized. The elucidation of the substituent's effect was further investigated by means of DFT calculations (free-energy calculations, NBO analysis), both in the initial substituted coumarins and in the formed radicals. It was observed that the presence of substituents at the C-6 and C-8 positions in the coumarin moiety would not affect significantly the formation of a radical, while a group at position C-7 could either stabilize or destabilize the formed radical depending on the electronic properties of the substituent. [ABSTRACT FROM AUTHOR]

Coumarins are natural products commonly found in plants and are typical allelopathic substances that strongly affect the growth of plants after being exudated from the root and help plants absorb Fe in cases of iron deficiency. Although coumarins have been found to have multiple effects, this understanding is still relatively limited. Here, we show that coumarin significantly promotes the elongation of the hypocotyl by enhancing cell elongation. Further research has found that coumarin increases the content of BR in plants by enhancing the expression of brassinosteroid (BR) synthesis genes. The effect of coumarin on promoting hypocotyl elongation is completely blocked by the mutation of the BR synthesis gene DEETIOLATED 2 (DET2) or the co-addition of the BR synthesis inhibitor brassinazole (BRZ). Genetic analysis using Arabidopsis mutants showed that coumarin promoting hypocotyl elongation depends on the signaling pathway of the BRs. Overall, coumarin promotes elongation of the hypocotyl by increasing the synthesis of BRs in plants. These results provide us with new insights into the role of coumarins and offer strong theoretical support for the mechanisms of interactions between plants. [ABSTRACT FROM AUTHOR]

Novel N-arylacetamides 2a–f were synthesized based on benzo[d]thiazole scaffold. The compounds 2a–c underwent Knoevenagel condensation through green synthetic method with different aromatic aldehydes and pyrazole-7-carbaldehydes delivered the respective arylidenes with efficient yields. Arylidenes 4 reacted with malononitrile affording the corresponding N-arylpyridones 11a–i. Moreover, the reaction of 2a–c with each of salicylaldehyde and 5-arylazo salicylaldehydes afforded the unexpected coumarins rather than quinolin-5-ones. The structure of coumarin 8 was confirmed by density functional theory (DFT) calculations using basis set B3LYP/6-311 G + + (d,p) to obtain the suitable geometrical structure with molecular orbitals' energies revealing its planar structure and its agreement with experimental data. Besides, the antibacterial activity was tested against different bacterial strains revealing potent activity especially Gram-negative bacteria with excellent minimum inhibition concentration (MIC) value ranging from 31.25 to 250 µg/L. Additionally, compounds 2c and 4m showed enzyme inhibition against dihydrofolate reductase in Escherichia coli with greater potency (IC50 for 2c = 3.796 µM, IC50 for 4m = 2.442 µM) than the standard antibiotic trimethoprim (IC50 = 8.706 µM). Investigation of the physicochemical properties of the newly compounds exhibited their better ADME properties that can be developed for the discovery of new antibacterial agents. [ABSTRACT FROM AUTHOR]

A [4+2] annulation reaction of o-acylamino-aryl MBH carbonates with 3-substituted coumarins has been developed. This method exhibits excellent substrate tolerance and constructs a series of tetrahydrochromeno[4,3-b]quinolin-6-ones with yields up to 95%. The application value of this method has also been demonstrated through a 50-fold scale-up. [ABSTRACT FROM AUTHOR]

Diastereoselective Giese addition on coumarin-3-carboxylate bearing a chiral auxiliary with N -hydroxyphthalimide ester to generate the corresponding alkylated adduct has been explored. Among screened chiral auxiliaries, bulkier one with appropriate steric hindrance is better for diastereoselective addition. Mechanistic studies involving fluorescence studies and On/Off experiments shed insight onto the plausible reaction pathway. [ABSTRACT FROM AUTHOR]

Iisatin hybrids have emerged as effective weapons against diseases. In this context, chalcone tethered isatin-coumarin hybrid 3 was synthesized and used as a building block for the preparation of a new series of isatin-pyrazole, isatin-bridged dibenzo-diazonin and isatin-coumarin hybrids 4–10 by reaction with ammonium acetate or primary aromatic amines. The hybrids 4–10 were linked with bioactive linkers named ethene, furan, pyrrole or its derivatives. Through another reaction route, the polyfused pyrano-indoles 11–13 were synthesized by one pot reaction of isatin - coumarin hybrid 3 with some primary amines having electron donating substituents. The chemical structures of the synthesized compounds were evaluated by infrared, nuclear magnetic resonance, MS and elemental analyses. The synthesized compounds were screened for their antioxidant, anti-inflammatory and antimicrobial effects. The results revealed that all the compounds have high antioxidant activity and some of these compounds provide anti-inflammatory effects close to that of indomethacin. While the antimicrobial effects were studied against both Gram - positive and Gram-negative bacteria, greater activity for compounds 3 and 6 was observed against Gram-positive bacteria (B. Subtilis). While compounds 3, 4, 6, 9 and 10 were active against Gram-negative bacteria (E. coli). [ABSTRACT FROM AUTHOR]

Copyright of Shipin Kexue/ Food Science is the property of Food Science Editorial Department and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

Viola, an edible wild plant, is valued for its distinctive flavor and health-promoting properties. This study examines the proximate composition, bioactive compounds, and in vitro biological activities of seven Viola leaves (Viola prionantha, Viola collina, Viola acuminata, Viola variegata, Viola tokubuchiana var. takedana, Viola mirabilis, and Viola philippica). Findings reveal that the leaves of the seven Viola species are rich in phenolic compounds (131.13 mg gallic acid equivalents (GAE)/100 g fresh weight (FW)–384.80 mg GAE/100 g FW), flavonoids (13.09 mg rutin equivalents (RE)/100 g FW–40.08 mg RE/100 g FW), fatty acids (palmitic acid, linoleic acid, oleic acid, and α-linolenic acid), and essential minerals, such as potassium, calcium, and magnesium. The leaf extracts demonstrated significant inhibitory effects on α-glucosidase (84.17%) and pancreatic lipase (77.54%) at a concentration of 1 g of extract per milliliter of solution. Additionally, the biological activity of Viola leaves, particularly their antioxidant capacity, is associated with their phenolic and flavonoid content, with caffeic acid contributing up to 35.2% of the total phenolic acids and isoquercitrin being one of the most bioavailable flavonoids. These results indicate that Viola offers potential notable health benefits, presenting a valuable addition to enhancing modern dietary patterns and overall health. [ABSTRACT FROM AUTHOR]

Twenty-two coumarins and twenty-six flavonoids were quantitated in fingered citron in different growth periods. Limettin was the top coumarin, and diosmin was the highest flavonoid, followed by hesperidin. Antioxidant evaluation by DPPH, ABTS, and FRAP indicated extracts of fingered citron in three growth periods all showed good antioxidant activity, which was positively correlated with the concentration of extracts. The oxidative stress model of RAW264.7 cells indicated extracts from fingered citron effectively reduced the contents of NO, MDA, and ROS in cells and increased the activity of SOD, thereby alleviating cell damage. The antioxidant capacity of fingered citron in November was the highest, followed by July and September. And there was a significantly positive correlation between the total flavonoid content and the antioxidant capacity. Diosmin, hesperidin, and neohesperidin were the main contributors to antioxidation. This study has significance for utilization of fingered citron germplasm resources and development of related functional products. [ABSTRACT FROM AUTHOR]

Prangos uechtritzii Boiss & Hausskn stands out for its rich bioactive constituents including prantschimgin (PRA), imperatorin (IMP), suberosin (SUB), adicardin (ADI), and oxypeucedanin hydrate (OPH) in the Apiaceae family. Although these molecules contribute to several biological activities, their mitochondrial toxicity were not illuminated in depth with the appropriate in vitro and in silico models. Cell viability studies investigated the cytotoxic activities of molecules in HepG2 cells by replacing glucose with galactose due to Warburg effects. Mitochondrial toxicity (mitotoxicity) parameters such as cellular adenosine triphosphate (ATP) and mitochondrial membrane potential (MMP) levels were assessed with cytotoxic concentrations of selected molecules. Molecular docking and dynamics studies were also conducted against mitochondrial electron transport chain (ETC) complexes (I-V) with selected compounds. In vitro results showed that PRA, SUB, and IMP reduced cell viability more in galactose media compared to high glucose media in a dose-dependent manner. PRA, IMP, and SUB decreased ATP levels and MMP, especially in the galactose medium. The in silico study revealed that PRA, IMP, and SUB might bind to complexes I-V at different levels. The docking study demonstrated that PRA had the highest binding potential with the complexes, higher than the standard ligands in some cases. The molecular dynamics (MD) simulation study showed that PRA formed stable complexes with complexes II, III, and IV. In addition, PRA was anticipated to remain inside the binding site of complex II most stably during the 230 ns simulation period. Our study suggests that PRA, IMP, and SUB exhibit mitotoxicity. [ABSTRACT FROM AUTHOR]

A catalytic system comprising a gold(I) complex with an N‐heterocyclic carbene (NHC) ligand in an ionic liquid as solvent exhibits higher catalytic efficiency compared to state of the art systems in the title reaction, which enables using down to 0.01 mol % gold. A commercial gold(I) catalyst such as IPrAuNTf2 can be employed for this purpose. In the case of less reactive substrates bearing electron‐withdrawing substituents at the phenol moiety, a tailor made NHC‐gold(I) precatalyst exhibits improved reactivity and can be advantageously employed compared to the commercial one. [ABSTRACT FROM AUTHOR]

Three previously undescribed coumarins (1–3) were obtained from the roots of Notopterygium incisum. Their chemical structures were elucidated using a variety of spectroscopic techniques and chemical calculations. The inhibitory effects of these new compounds on NO production and pro-inflammatory factors (IL-1β, IL-6, and TNF-α) in LPS-stimulated RAW 264.7 cells were investigated. Further studies revealed that compound 1 suppressed the expression of COX-2 and iNOS while also reduced ROS accumulation. Western blot analysis demonstrated that compound 1 could inhibit the PI3K/AKT pathway by decreasing the levels of p-PI3K and p-AKT. Collectively, these findings suggest that compounds 1–3 exhibit promising anti-inflammatory properties. [ABSTRACT FROM AUTHOR]

The cyclization of various nucleophiles, such as 1,3-dicarbonyl compounds, 1,3-bis(silyloxy)-1,3-butadienes, hydrazones, hydroxylamine, amidines, thioglycolic esters, heterocyclic enamines and others, with 4-chlorocoumarins, containing an electron-withdrawing group at position 3, allows for a convenient synthesis of a great variety of benzo[c]coumarins and related fused coumarins. Suzuki–Miyaura reactions of coumarin-derived bis(triflates) result in formation of arylated coumarins with excellent regioselectivity that is controlled by electronic and steric features of the substrate. The combination of Suzuki–Miyaura with lactonization reactions of carba- and heterocyclic substrates allows for the synthesis of benzo[c]coumarins and of other fused coumarins. Domino Michael–retro-Michael–lactonization reactions of 1,3-bis(silyloxy)-1,3-butadienes with chromones provide a convenient access to hydroxylated benzo[c]coumarins. In a related approach, fused coumarins were prepared by domino reactions of heterocyclic enamines with chromone-3-carboxylic acids. 1 Introduction 2 Reactions of 3-Acceptor-4-chlorocoumarins 3 Reactions of Coumarin Triflates 4 Synthesis of Fused Coumarins 5 Conclusions [ABSTRACT FROM AUTHOR]

Developing and creating novel antibiotics is one of the most important targets in treating infectious diseases. Novel coumarins were synthesized and characterized using different spectroscopic techniques such as Fourier Transform Infrared (FTIR), Nuclear magnetic resonance1H and 13C and mass spectroscopy (MS). All of the synthesized compounds have been tested for activity and sensitivity against the microbial strains of B. subtilis, S. aureus, E. coli, P. aeruginosa, S. typhi, and C. albicans. All compounds showed substantial results against the tested microbes except S. typhi, which was not affected in any way by these coumarins. Exceptional results were shown by compounds 4, 6d, and 8b, which made them the best candidates for loading to the vicinity of nanostructure lipid carrier and coated by chitosan nanocapsule (NLC-Cs). Transmission electron microscope (TEM) confirmed spherical morphology with particles size less than 500 nm. Also, dynamic light scattering (DLS) were utilized to measure the average particle size (between 100 and 200 nm) and the stability assessed by zeta potential were found to be more positive confirming the chitosan encapsulation. Antimicrobial activity assessments were performed for both synthetic compounds and their NLCs analogues. The nanoformulation of 4-NLC-Cs, 6d-NLC-Cs, and 8b-NLC-Cs manifested unique biological results, especially 8b-NLC-Cs, which revealed powerful effects over all the tested organisms including S. typhi. The increasing biological effect of the drugs in their nanoscale form is reflected in the increasing value of inhibition zone diameter and suppressing the value of MIC to reach record levels like 8b-NLC-Cs disclosed MIC = 0.48 and 0.24 µg/ml against S. aureus and C. albicans, respectively, by the mean 8b-NLC-Cs nanoformulation suppressed the MIC by 65 folds of its initial value before nano. In continuation, it was proven that the compounds 4, 6d and 8b were found to make noticeable changes on the DNA-Gyrase levels with reduced IC50 values particularly 8b showed excellent inhibitory effect with IC50 = 4.56 µM. TEM was used to pursue the morphological changes that occur in bacterial cells of P. aeruginosa. The weakness of the cell wall in most bacterial cells treated with nanomaterials, 8b-NLC-Cs, has reached the point of the cell wall rupture and the cell components spilling out of the cells causing necrotic cell death. [ABSTRACT FROM AUTHOR]

Respiratory syncytial virus (RSV) is one of the most prevalent viruses that causes severe acute lower respiratory tract infections (ALRTIs) in the elderly and young children. There is no specific drug to treat RSV, only a broad-spectrum antiviral, ribavirin, which is only used in critical cases. Our research group is investigating antiviral agents of natural origin, such as coumarins and flavonoids, that may help reduce or prevent RSV infection. The cytotoxic concentrations of coumarins and hesperetin were tested on A549 and HEp-2 cells and used in inhibition tests in which 80% of the cells were viable. The anti-RSV action of the molecules was analyzed in A549 and HEp-2 cells and in HBE cell cultures infected with RSV-luc or rgRSV. We also encapsulated the compounds using β-cyclodextrin to improve the permeability and solubility of the molecules. Esculetin and 4-methyl inhibited rgRSV effectively on A549 and HEp-2 cells after 24 hpi, and when they were encapsulated, coumarin, esculetin, and hesperetin presented inhibition against rgRSV in HBE culture. The coumarins inhibit RSV replication in cell culture and even manage to overcome the mucus barriers of the HBE cultures, and β-cyclodextrin was essential for some of the coumarins to enter the cell and therefore to reach their targets. [ABSTRACT FROM AUTHOR]

Background: Accumulation of coumarins plays key roles in response to immune and abiotic stress in plants, but the genetic adaptation basis of controlling coumarins in perennial woody plants remain unclear. Results: We detected 792 SNPs within 334 genes that were significantly associated with the phenotypic variations of 15 single-metabolic traits and multiple comprehensive index, such as principal components (PCs) of coumarins metabolites. Expression quantitative trait locus mapping uncovered that 337 eQTLs associated with the expression levels of 132 associated genes. Selective sweep revealed 55 candidate genes have potential selective signature among three geographical populations, highlighting that the coumarins biosynthesis have been encountered forceful local adaptation. Furthermore, we constructed a genetic network of seven candidate genes that coordinately regulate coumarins biosynthesis, revealing the multiple regulatory patterns affecting coumarins accumulation in Populus tomentosa. Validation of candidate gene variations in a drought-tolerated population and DUF538 heterologous transformation experiments verified the function of candidate genes and their roles in adapting to the different geographical conditions in poplar. Conclusions: Our study uncovered the genetic regulation of the coumarins metabolic biosynthesis of Populus, and offered potential clues for drought-tolerance evaluation and regional improvement in woody plants. [ABSTRACT FROM AUTHOR]

An efficient method was developed for the synthesis of eight novel functionalized 1,2,4,3-triazaphospholes and one 1,3,2-thiazaphosphinine incorporating a coumarin ring. Additionally, two interesting examples of diethyl coumarinyl phosphonate and diethyl chromeno-[3,4-c][1,2,4]triazolo[4,3-a]pyridinyl phosphonate were obtained. The proposed methodology involved the treatment of N'-benzoyl-2-oxo-2H-chromene-3-carbohydrazonamide (2) with various phosphorus agents, including phosphorus halides, phosphorus triamide, phosphorus esters, and phosphorus sulfides. IR, NMR, and mass spectrometric methods were used to confirm the structures of the prepared compounds. The antiproliferative properties of the isolated compounds were screened against HepG-2, MCF-7, and A549 cancer cells. The products 5, 7, 9, and 10 exhibited excellent cytotoxic properties compared with doxorubicin. These four bioactive compounds have low toxicity in healthy human HFB4 cells. [ABSTRACT FROM AUTHOR]

Diabetes and its associated conditions are significant causes of morbidity and mortality. Despite the abundance of available medications for diabetes treatment, their limitations have spurred ongoing research in this field. Consequently, there is a need to discover a potential therapeutic molecule for managing diabetes and its complications. In current research work a series of novel coumarin analogs (5a–5e) were designed, synthesized, characterized through FTIR, 1H NMR, 13C NMR, and mass spectroscopy and evaluated for antidiabetic property. Molecular docking study was performed to link its binding affinity toward AMPK. DPPH scavenging assay was performed for in vitro antioxidant activity, for reference standard ascorbic acid was taken. In vivo hypoglycemic activity was performed on streptozotocin and nicotinic acid induced diabetic rats. All synthesized molecule showed good docking, score among them compound 5b has lowest docking score −11.25 kcal/mol. Molecule 5b and 5c showed greater antioxidant potential with good IC50 value, i.e., 20.4 g/mL and 21.6 g/mL. In vivo antidiabetic study showed good control on blood glucose level, cholesterol, triglyceride, Hb1AC as well as SGOT and SGPT level on animals fed 5b when compared to metformin. This result showed that test molecule 5b has potential to lower the blood glucose level without causing any toxicity. [ABSTRACT FROM AUTHOR]

Fe3O4@APIDSO3H as a novel and magical magnetic nanocatalyst was designed, synthesized, and characterized by different spectroscopic techniques such as Fourier transform infrared (FT‐IR) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), x‐ray diffraction (XRD), energy‐dispersive x‐ray (EDX), thermogravimetric analysis (TGA), and vibrating sample magnetometer (VSM). The loading percentage of sulfonic acid on the magnetic nano catalyst was calculated using CHNS analysis. Then, the potential use of it was investigated for the synthesis of various coumarins by Pechmann condensation. The corresponding products were synthesized and isolated in 60%–99% yields. The catalyst was recycled and reused for four times without loss in catalytic activity. [ABSTRACT FROM AUTHOR]

Background: Vector-borne diseases, such as leishmaniasis and arboviral infections, represent a great challenge to human health with limited therapeutic options. In addition, sexually transmitted infections, such as herpes, affect billions of people worldwide and the emergence of new strains resistant to common antivirals, such as acyclovir (ACV), poses a serious threat to humans. In this context, coumarins have proved to be a valuable source of new derivatives with promising biological activities to fight these diseases. Methodology: 3-aryl and/or 4-(N-aryl)aminocoumarins were synthesized, and their drug-like profile was evaluated using silico tools. Their biological activity against Leishmania amazonensis promastigotes was evaluated using the MTT assay, while their antiviral activity against replication of Chikungunya, Mayaro, Zika, and type 1 Herpes simplex virus (HSV-1) in Vero cells was analyzed using plaque reduction assays. Results: The in silico studies pointed to satisfactory pharmacokinetic and toxicological properties as drug candidates. Hence, their antileishmanial activity was evaluated. None of the compounds exhibited significant activity and compound 2b showed the highest activity (IC50 = 47.10 µM). We further evaluated their cytotoxicity and antiviral activity. Compound 2e showed good activity against ACV-sensitive and -resistant HSV-1 strains with EC50 values of 48.68 µM and 66.26 µM, respectively (selectivity index values of 12.5 and 9.2). Mechanism of action studies indicated that this compound acts at late steps of HSV-1 replication, such as virus egress. Conclusions: Compound 2e possesses a different mechanism of action compared to ACV and presents a promising alternative for the treatment of HSV-1 infections. [ABSTRACT FROM AUTHOR]

1-[4-(Phenyldiazenyl)phenyl]-1H-1,2,3-triazole and 3-(1H-1,2,3-triazol-1-yl)-2H-chromen-2-one were synthesized for the first time by using the copper-catalyzed azide-alkyne cycloaddition reaction of azobenzene- and coumarin-substituted azides and calcium carbide-derived acetylene. Both azobenzene- and coumarin-substituted substrates afforded target 1,2,3-triazoles in good yields by reacting with acetylene generated from calcium carbide and water directly in the reaction vessel. This work demonstrates the enhanced applicability of the calcium carbide approach in organic synthesis, including the synthesis of chromophore- and fluorophore-substituted compounds. [ABSTRACT FROM AUTHOR]

This study focuses on synthesis and characterization of hexa-substituted coumarin based Schiff base derivative of cyclotriphosphazene (Compound 3). The antibacterial activity of Compound 3 was evaluated against Gram-positive Staphylococcus aureus (S. aureus) and Gram-negative Pseudomonas aeruginosa (P. aeruginosa), and Klebsiella pneumoniae (K. pneumoniae) bacterial strains using minimum inhibitory concentration (MIC) and percentage-killing method. Compound 3 exhibited a lower MIC of 300 μg/mL against S. aureus than 500 μg/mL for P. aeruginosa and K. pneumoniae, indicating greater efficacy against Gram-positive bacteria. Percentage-killing data confirmed Compound 3 significant bactericidal activity against S. aureus across concentrations ranging from 100 to 500 μg/mL, comparable to ampicillin. In contrast, its efficacy against Gram-negative strains was lower, suggesting a more selective spectrum of activity. These findings suggest that Compound 3 shows promise as a potential antibacterial agent with preferential activity against Gram-positive bacteria, warranting further investigation into its mechanism of action and therapeutic potential. [ABSTRACT FROM AUTHOR]

The phytochemical investigation of the methanol extract of the seeds of Magydaris pastinacea afforded two undescribed benzofuran glycosides, furomagydarins A-B (1, 2), together with three known coumarins. The structures of the new isolates were elucidated after extensive 1D and 2D NMR experiments as well as HR MS. Compound 1 was able to inhibit the COX-2 expression in RAW264.7 macrophages exposed to lipopolysaccharide, a pro-inflammatory stimulus. RT-qPCR and luciferase reporter assays suggested that compound 1 reduces COX-2 expression at the transcriptional level. Further studies highlighted the capability of compound 1 to suppress the LPS-induced p38MAPK, JNK, and C/EBPβ phosphorylation, leading to COX-2 down-regulation in RAW264.7 macrophages. [ABSTRACT FROM AUTHOR]

Novel coumarin derivatives were synthesised and tested for their cytotoxicity against human cancer cells (PC-3 and MDA-MB-231). Compounds 5, 4b, and 4a possessed potent cytotoxic activity against PC-3 cells with IC50 3.56, 8.99, and 10.22 µM, respectively. Compound 4c displayed cytotoxicity more than erlotinib in the MDA-MB-231 cells with IC50 8.5 µM. Moreover, compound 5 exhibited potent inhibitory activity on EFGR with IC50 0.1812 µM, as well as PI3Kβ inhibitory activity that was twofold higher than LY294002, suggesting that this compound has a dual EGFR and PI3Kβ inhibiting activity. Docking aligns with the in vitro results and sheds light on the molecular mechanisms underlying dual targeting. Furthermore, compound 5 decreased AKT and m-TOR expression in PC-3 cells, showing that it specifically targets these cells via the EGFR/PI3K/Akt/m-TOR signalling pathway. Simultaneously, compound 5 caused cell cycle arrest at S phase and induced activation of both intrinsic and extrinsic apoptotic pathways. [ABSTRACT FROM AUTHOR]

Many molecules called coumarins with very varied biological activities and widely used in the food, pharmaceutical, cosmetic, and medical industries. Their structure has a significant impact on their biological activity and their possible applications. Advanced synthesis frequently leads to an increase in the production of various chemical wastes. The amount of hazardous organic substances used and produced is reduced by the application of environmentally friendly synthesis techniques. Numerous techniques are employed in green chemistry, including the use of ionic liquids and deep eutectic solvents, solvent‐free synthesis, mechanical synthesis, multicomponent reactions, ultrasound, and microwaves. These green synthesis techniques have been successfully applied to all common condensation reactions for the synthesis of coumarin, including the Perkin, Knoevenagel, Pechmann, Kostanecki‐Robinson, and Reformansky reactions. These methods not only reduce the use and production of toxic chemicals, but also improve the yield, purity, and energy consumption of the product. This review summarizes the methods of microwave synthesis of coumarin derivatives, as well as their biological activities. [ABSTRACT FROM AUTHOR]

Recently, 7-diethylamino-4-methylcoumarin (DEAMC) has been identified as a potent antiandrogenic compound in the surface water; however, little is known about the antiandrogenic potentials of other synthetic coumarins and their occurrence in the aquatic ecosystem. In this study, for the first time, we observed that 7-dimethylamino-4-methylcoumarin (DAMC) elicited androgen receptor (AR) antagonistic activity with a 50% inhibitory concentration (IC50) of 1.46 µM, which is 14.3 times more potent than that observed for DEAMC (IC50 = 20.92 µM). We further collected abiotic (water and sediment) and biotic (plant, plankton, and fish) samples (n = 208) from a subtropical freshwater ecosystem, the Dongjiang River basin, in southern China, and determined the concentrations of the two coumarins in these samples. Overall, DAMC was the predominant compound found in the sediment, plant, algae, zooplankton, and fish muscle samples, with median concentrations at 0.189, 0.421, 0.832, 0.798, and 0.335 ng/g dry wt. (DW), respectively, although it was not detected in any surface water sample. For DEAMC, the median concentrations observed in the surface water, sediment, plant, algae, zooplankton, and fish muscle samples were 0.105 ng/L, 0.012, 0.051, 0.009, 0.008, and 0.181 ng/g DW, respectively. The bioaccumulation factor (BAF) values of DAMC and DEAMC in the algae, zooplankton, and fish muscle exceeded 5000 L/kg, suggesting that the two coumarins may have significant bioaccumulation potentials in aquatic biota. Additionally, the mean daily intake (EDI) of coumarins through fish consumption was estimated as 0.19 ng/kg BW/day for male toddlers. This is the first field study to illustrate the antiandrogenic potential of DAMC and document the widespread occurrence of the two synthetic coumarins in aquatic ecosystems. [ABSTRACT FROM AUTHOR]

Copyright of Adiyaman University Journal of Science & Technology / Adıyaman Üniversitesi Fen Bilimleri Dergisi is the property of Adiyaman University, Institute of Science / Adiyaman Universitesi Fen Bilimleri Enstitusu and its content may not be copied or emailed to multiple sites or posted to a listserv without the copyright holder's express written permission. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)

The major threat to public health due to the outbreak of severe acute respiratory syndrome coronavirus‐2 (SARS‐CoV‐2) infection has been recognised as a global issue. The increase in morbidity is primarily due to the lack of SARS‐CoV‐2 specific drugs. One of the major strategies to combat this threat is to deactivate the enzymes responsible for the replication of corona virus. To this end, 3‐arylidene/3‐hydroxycoumarin induced deactivation of 3‐chymotrypsin like protease (3CLpro) enzyme, which takes the pivotal role in the replication and maturation, was investigated. For ready availability of the compounds for the above investigation, we have developed a user‐friendly protocol for the synthesis 3‐hydroxycoumarin derivatives from cheap and readily available starting materials in two steps; i) Bronsted acid catalysed Friedel‐Crafts alkylation of phenols with Morita‐Baylis‐Hillman adducts followed by intramolecular lactonization to trans‐3‐arylidenechroman‐2‐ones in one‐pot and ii) ozonolysis in reasonably good yields. Pharmacokinetic assessments of coumarin derivatives revealed drug‐like characteristics with moderate or low toxicity values. Notably, these hydroxycoumarins exhibited enhanced binding affinity against the 3CL protease of SARS‐CoV‐2, fitting well into the binding pocket akin to the previously studied inhibitor N3. Furthermore, a molecular dynamics study elucidated the dynamic behaviour of these small molecules when bound to the protein, showcasing intriguing complexities within the active site. Despite backbone variations and residual fluctuations, compounds 3 d–f and 6 a exhibited a consistent behaviour, instilling confidence in the therapeutic potential of these coumarins for combating SARS‐CoV‐2. [ABSTRACT FROM AUTHOR]

A rapid metal‐free approach describing one‐pot thiocyanation of chromone and coumarin enabling tandem cyclization via potassium thiocyanate as a sulfur surrogate was unveiled. Interestingly, this enaminone‐mediated protocol facilitated straightforward access to medicinally significant 2‐amino/imino thiazolo fused chromone and coumarin frameworks. This methodology provided good atom‐economy, remarkable functional group tolerance, and scalability. Alongside establishing a wide substrate scope, it also provided a feasible scalability up to gram scale. [ABSTRACT FROM AUTHOR]