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The preparation of Chalcones and Pyrazoline derivatives from different aromatic ketones and substituted aldehydes is detailed. Chalcones were produced by reacting aldehydes with substituted aromatic ketones, such as acetophenones, in the Claisen-Schmidt condensation reaction. Cyclohexenone derivatives are produced when ethyl aceto aromatic ketones undergo base-catalyzed cyclo-condensation to Chalcones under microwave radiation. The synthesized compounds are characterized using spectrum techniques from 1H NMR, 13C NMR, and IR. These are examined for their antioxidant qualities as well as their antibacterial action against Staphylococcus aureus, Escherichia coli, Aspergillus niger, and Aspergillus flavus. [ABSTRACT FROM AUTHOR]

Fungal infections can be serious or life threatening in severe cases, and the need to discover and find novel antifungal agents persists. Chalcones are plant-derived aromatic compounds that have been appealing synthons for pharmaceutical industry as they have good anticancer, antibacterial, antifungal and anti-inflammatory properties. Although there are few structure–activity relationship studies on chalcones, studies that link the structural features of these compounds to their mode of action are scant. Thus, in this study, we aim to clarify the relationship between chalcone derivatives and their cellular target within the yeast cell Saccharomyces cerevisiae. We observed that some chalcone compounds lead to disruption of cell membrane and cause ion leakage out of the cell. Moreover, chalcones alter the biochemical composition of yeast cells detectable by FTIR spectroscopy and bind to the DNA as shown by our titration experiments based on UV–Vis absorbance spectroscopy. Thus, their interaction with the DNA may be the major impact of these compounds on yeast cells. [ABSTRACT FROM AUTHOR]

Aronia melanocarpa (Michx.) Elliott, ×Sorbaronia fallax (C. K. Schneid.) C. K. Schneid. nothosubsp. fallax, and ×Sorbaronia fallax nothosubsp. mitschurinii (A. Skvortsov & Maitul.) A.Stalažs, belonging to the Rosaceae family, are grown as fruit plants. They are known to horticulturists as garden chokeberry or black chokeberry. The fruit of these species is the richest source of biophenols in the plant kingdom and suitable raw material for the production of functional foods with high nutraceutical value. The work aimed to examine the basic and polyphenolic composition of fruit chokeberry and rowan-chokeberry hybrids of different taxonomic groups. Experimental plants were grown at the orchard of the National University of Life and Environmental Sciences of Ukraine in the Kyiv region. Fruit of 10 cultivars developed in Belorussia, the Czech Republic, Finland, Russia, Ukraine, and the USA were collected during 2020 and 2021. The fruit was analyzed for dry matter, soluble solids, sugars, pectin substances, organic titratable acidity, ascorbic acid, and biophenols. Chokeberry fruit contains on average 24.4–29.2% dry matter, 16.0–21.1% soluble solids, 6.5–8.9% sugars, 0.40–0.80% pectin, and 0.95–2.15% organic acids on raw material. Bioactive components of chokeberry fruit are ascorbic acid (24.7–45.9 mg/100 g), total polyphenols (998–4840 mg/100 g), including anthocyanidins (9–217 mg/100 g), flavonoids (23–1422 mg/100 g), and chalcones (9–59 mg/100 g). If the group ×S. fallax nothosubsp. mitschurinii cultivars is morphologically constant and like A. melanocarpa simple in leaf shape, then the group ×S. fallax nothosubsp. fallax cultivars was different in the morphology of leaves from lobate to pinnate and fruit color from purple to black in the study. Chokeberry fruit composition varied between each year and especially between taxonomic groups and cultivars. Fruit harvested in 2021 had the lowest dry matter, soluble solid, sugars, and ascorbic acid in comparison with 2020. In contrast, titrated acidity was consistent between years. The fruit of garden chokeberries is a good source of ascorbic acid. ×S. fallax cultivars with the exception ‘Titan’ are richer on ascorbic acid. The fruit of A. melanocarpa ‘Dwarf’ has the highest content of total polyphenols, flavonoids, and chalcones. There are significant differences between ×S. mitschurinii cultivars in biochemical content. Purple-fruited ‘Titan’ has the lowest content of all biologically active substances, than other cultivars belonging to the same ×S. fallax taxonomic group. The black-fruited ×S. fallax nothosubsp. fallax genotypes, including the first chokeberry cultivar ‘Vseslava’ of Ukrainian breeding, often have a high or the highest content of ascorbic acid, total polyphenols, anthocyanidins, flavonoids, and chalcones, which is valuable for garden chokeberry breeding. [ABSTRACT FROM AUTHOR]

A library of imidazo[1,2‐a]pyridine‐appended chalcones were synthesized and characterized using 1H NMR, 13C NMR and HRMS. The synthesized analogues were screened for their antikinetoplastid activity against Trypanosoma cruzi, Trypanosoma brucei brucei, Trypanosoma brucei rhodesiense and Leishmania infantum. The analogues were also tested for their cytotoxicity activity against human lung fibroblasts and primary mouse macrophages. Among all screened derivatives, 7f was found to be the most active against T. cruzi and T. b. brucei exhibiting IC50 values of 8.5 and 1.35 μM, respectively. Against T. b. rhodesiense, 7e was found to be the most active with an IC50 value of 1.13 μM. All synthesized active analogues were found to be non‐cytotoxic against MRC‐5 and PMM with selectivity indices of up to more than 50. [ABSTRACT FROM AUTHOR]

Pathological angiogenesis plays a critical role in tumorigenesis and tumor progression, and anti-angiogenesis therapies have evinced promising antitumor effects in solid tumors. Chalcone skeleton has been regarded as a potential antitumor agent that also targets angiogenesis. In this study, we designed twenty-one non-fluoro-substituted chalcones (13–18, 24–27) and saturated chalcone derivatives (19–23, 28–33) as anti-angiogenic compounds. During the initial stage, these compounds were assessed for their anti-cancer activities against MCF-7 cancer cell lines according to the MTT assay. The compounds revealed satisfactory anti-proliferative capability. An ex vivo fertilized hens' egg-chorioallantoic membrane (HET-CAM) angiogenic study was conducted for the compounds to gauge their mortality and toxicity, which, in turn, revealed a potent anti-angiogenic effect. Eight compounds (16, 17, 21, 24, 26, 27, 29, and 31) significantly reduced densities of capillaries on CAM, whereas compounds 27 and 29 were the most effective anti-angiogenic agents, when compared with Suramin. Moreover, RT-qPCR analysis demonstrated that the anti-angiogenic activity was associated with the fold changes of VEGFR2. Molecular docking studies were conducted for compounds to investigate their mode of interaction within the binding site of VEGFR-2 kinases. This work provided a basis for further design, structural modification, and development of chalcone derivatives as new anti-angiogenic agents. [ABSTRACT FROM AUTHOR]

The present work focuses on the synthesis and preliminary structure activity relationships (SARs) of furan-derived chalcones and their corresponding ∆2-pyrazoline derivatives as antimicrobial agents. Eight novel chalcone derivatives and eight ∆2-pyrazoline compounds were synthesized in moderate to good isolated yields. The target compounds were evaluated as antimicrobial agents against two Gram-positive (Staphylococcus aureus and Staphylococcus epidermidis), two Gram-negative (Escherichia coli and Klebsiella pneumoniae), and fungi (Candida albicans) species. Based on the SARs, chalcones 2a and 2h showed inhibition activity on all tested microbial species, while ∆2-pyrazoline 3d was found to be selective for some microbial species. The most potent compounds (2a, 2h, and 3d) were docked into glucosamine-6-phosphate synthase (GlcN-6-P), the molecular target enzyme for antimicrobial agents, utilizing the Autodock 4.2 program, in order to study their virtual affinity and binding mode with the target enzyme. The selected potent compounds were found to bind to the active site of the enzyme probably in a similar way to that of the substrate as suggested by the docking study. In summary, the newly developed furan-derived chalcones and their ∆2-pyrazoline derivatives could serve as potent leads toward the development of novel antimicrobial agents. [ABSTRACT FROM AUTHOR]

The rise of drug‐resistant microbes necessitates the development of new antimicrobial agents. Increasing resistance among multidrug‐resistant microbes has spurred research efforts to overcome drug resistance through novel scaffolds and strategies. Chalcones, distinguished by their chemical structure of 1,3‐diphenylprop‐2‐en‐1‐one, have exhibited a multifaceted array of biological activities, prominently including antimicrobial and antiviral properties. Modifying the structure by adding substituent groups to the aromatic ring enhances potency, reduces toxicity, and expands pharmacological effects. This review highlights the potential of chalcones and analogues in preventing diseases affected by diverse antibiotic resistance genes, including viruses, bacteria, fungal spores, and Plasmodiidae. Our analysis underscores the fact that a multitude of chalcone compounds effectively obstruct various molecular targets pivotal in the development of antibiotic resistance, thus rendering bacteria vulnerable to conventional antibacterial agents and potentially obliterating resistance mechanisms. Certain chalcone compounds exhibit higher activity levels compared to traditional antibiotics like vancomycin and tetracycline. Additionally, Docking and SAR studies of chalcones summarize their role in developing novel drugs. Chalcones and their derivatives demonstrate promising broad‐spectrum antimicrobial activities. Investigating structure‐activity relationships (SAR) enhances our understanding of chalcone‐based drug design, enabling the development of more effective therapeutic interventions against the pressing global health challenge of antimicrobial resistance. [ABSTRACT FROM AUTHOR]

A convenient protocol for the synthesis of thiazole‐2‐thiones from nitrobenzene, chalcones and carbon disulfide is described. The construction of one C−S bond and two C−N bonds via [3+2] cycloaddition reaction is achieved using NaOH as the base in one pot. Various functional groups attached to substrates were well tolerated to afford the corresponding products in moderate to good yields. [ABSTRACT FROM AUTHOR]

The mercuric acetate-pyridine-mediated cyclization reaction of aryl O-propargyl ethers of chalcones provided 8-phenyl-dibenzo[b,d]furan-1,7-diol and (E)-1-(4-hydroxy-3-styrylbenzofuran-2-yl)ethan-1-one via an unusual participation of O-propargyl group of ortho propargyl ethers is observed. The scope and limitations of the reaction and synthetic use of the products are provided. Based on control experiments and isolated products, a plausible reaction mechanism for forming unusual title compounds is provided. [ABSTRACT FROM AUTHOR]

Synthesized substituted N-acetyl-3,5-diaryl-2-pyrazolines through their chalcone intermediates and evaluated for anti-cancer activity. Chalcones were synthesized from 2,4,5-trimethoxy benzaldehyde obtained from oxidation of β-asarone ((Z)-2,4,5-trimethoxy-1-propenylbenzene) is a major active principle component found in Acorus calamus oil (70–80%) and reacting with substituted acetophenones by Claisen-Schmidt condensation. Substituted chalcones were further treated with hydroxylamine in presence of sodium acetate and acetic acid cyclizes to give directly the corresponding N-acetyl-3,5-diaryl-2-pyrazolines in 68–85% yields. Structures were confirmed by IR, GC-MS,1H NMR, and 13C NMR.These novel analogues were evaluated for their in vitro anticancer activity against three human tumor cell lines (MCF-7, SW-982, and HeLa) using MTT assay. The results reveled that among the synthesized pyrazolines, which are having electron donor groups in para position of the aryl ring, i.e. 5th position of the N-acetyl pyrazolines showed better inhibitory activity (5b, 5c, 5d, 5e, 5f, 5g, 5k, and 5j) when compared with β-asarone. The compound 3'-nitro, 4'-chloro pyrazolines (5k) showed highest IC50 values 11.67 ± 0.54, 14.17 ± 0.92, and 18.26 ± 0.98 µg/mL (P <0.05) respectively, when compared to natural precursor. [ABSTRACT FROM AUTHOR]

Efficient protocols have been developed for epoxidation of chalcones and hydration of nitriles to amides using "water extract of red mud (WERM)/H2O2" system at room temperature. As red mud is produced abundantly as wastes in aluminum industries, this present simple and cost-effective method is an alternative way of waste management which demands eco-friendly, greener and sustainable development. It has also been noticed that high yields of epoxides and amides could be obtained without any chromatographic separation. Further important characteristics of this protocol are its clean reaction profile, applicability for large-scale synthesis and high functional group tolerance. [ABSTRACT FROM AUTHOR]

Colon cancer poses a complex and substantial global health challenge, necessitating innovative therapeutic approaches. Chalcones, a versatile class of compounds with diverse pharmacological properties, have emerged as promising candidates for addressing colon cancer. Their ability to modulate pivotal signaling pathways in the development and progression of colon cancer makes them invaluable as targeted therapeutics. Nevertheless, it is crucial to recognize that although chalcones exhibit promise, further pre-clinical studies are required to validate their efficacy and safety. The journey toward effective colon cancer treatment is multifaceted, involving considerations such as optimizing the sequencing of therapeutic agents, comprehending the resistance mechanisms, and exploring combination therapies incorporating chalcones. Furthermore, the integration of nanoparticle-based drug delivery systems presents a novel avenue for enhancing the effectiveness of chalcones in colon cancer treatment. This review delves into the mechanisms of action of natural chalcones and some derivatives. It highlights the challenges associated with their use in pre-clinical studies, while also underscoring the advantages of employing chalcone-based nanoparticles for the treatment of colon cancer. [ABSTRACT FROM AUTHOR]

Ovarian cancer ranks as the eighth most prevalent form of cancer in women across the globe and stands as the third most frequent gynecological cancer, following cervical and endometrial cancers. Given its resistance to standard chemotherapy and high recurrence rates, there is an urgent imperative to discover novel compounds with potential as chemotherapeutic agents for treating ovarian cancer. Chalcones exhibit a wide array of biological properties, with a particular focus on their anti-cancer activities. In this research, we documented the synthesis and in vitro study of a small library of chalcone derivatives designed for use against high-grade serous ovarian cancer (HGSOC) cell lines, specifically OVCAR-3, OVSAHO, and KURAMOCHI. Our findings revealed that three of these compounds exhibited cytotoxic and anti-proliferative effects against all the tested HGSOC cell lines, achieving IC50 concentrations lower than 25 µM. Further investigations disclosed that these chalcones prompted an increase in the subG1 phase cell cycle and induced apoptosis in OVCAR-3 cells. In summary, our study underscores the potential of chalcones as promising agents for the treatment of ovarian cancer. [ABSTRACT FROM AUTHOR]

Natural chalcones are a kind of flavonoid. The chemical formula for chalcones is 1,3-diphenyl-2-propene-1-one, which consists of two aromatic rings connected by a, -unsaturated carbonyl system with three carbon atoms. Due to the existence of a double bond, both the Cis and Trans forms of keto ethylenic groups occur, with the Trans form being the thermodynamically preferred one. In order to further investigate its remarkable biological potential, chalcone has undergone a number of structural alterations in recent years. Antihypertensive, antifungal, anticancer, antifilarial, antiprotozoal, anti-human immunodeficiency virus (HIV), antimalarial, antioxidant, antiviral, antifungal, anticonvulsant, and antibacterial are only some of the pharmacological effects. [ABSTRACT FROM AUTHOR]

In this research, density functional theory (DFT) was used with the B3LYP functional hybrid and the 6–311++G(d,p) basis set for the geometry optimization. First, the findings of the scanning for the potential energy surface (PES) for the vinyl chalcone (VC) have shown that the s-cis conformer was more stable than the s-trans conformer. The data also indicated that 1-butenyl chalcone (1-BC) is the most stable conformer and significantly improves the stability of unsubstituted chalcone (CA). VC was shown to be the least stable conformer. Second, the results were further supported by measuring the thermodynamic parameters thermal energy (TE), entropy (S), and heat capacity (Cv). TE, S, and Cv increased with the stability of conformer and decreased with the increased polarity of the solvent. Finally, the computed C = O stretching vibrations indicated that divinyl chalcone (DVC) causes the largest shift in the peak center of the C = O stretching vibrations of CA by a deviation 4.79 cm−1 in the gas phase and 5.75 cm−1 in n-hexane. The UV–Vis spectra for the studied conformers were analyzed by time-dependent density functional theory (TD-DFT) and the results displayed that the most planar conformers DVC and 1-BC have the highest values of maximum wavelength (λmax). The results shown that CA possesses the highest electronegativity (χ) while trans propenyl chalcone (E-PC) possesses the lowest electronegativity. The dipole moment (µ), polarizability (α), and first hyper polarizability (β) were seen to increase with the π-conjugation and solvent polarity. E-PC, 1-BC, and DVC constituted the highest magnitudes of µ, α, and β. [ABSTRACT FROM AUTHOR]

Abiotic stresses, including drought, have been found to affect the growth and medicinal quality of numerous herbs. The proposed study aims to study the effects of different drought regimes on the metabolic profile, growth, ecophysiology, cellular antioxidants, and antioxidant potential of Nigella sativa (Black cumin) leaf. Forty-day-old seedlings of N. sativa were exposed to three regimes of drought (control, moderate and high) for a week. UPLCMS/ MS metabolic profile of the leaf reveals the presence of more than a hundred metabolites belonging to anthocyanins, chalcones, dihydro flavonoids, flavonoids, flavanols, flavones, flavonoid carbonoside, isoflavones, etc. Drought was found to alter the contents of identified metabolites. Drought stress-induced oxidative stress and increased production of hydrogen peroxide and superoxide anions. Physiological changes, activities of antioxidant enzymes, contents of antioxidants, and proline were significantly high under drought to protect against the low water regimes. Furthermore, stressed leaf extract had higher antioxidant potential. Thus, N. sativa leaf bears multiple metabolic pathways and can tolerate a higher degree of drought or osmotic stress. [ABSTRACT FROM AUTHOR]

Chalcones are a type of molecule that can be considered as easily synthesizable through aldol condensation or that can be readily purchased from habitual commercial vendors. However, on reviewing the literature, one realizes that there are no standard procedures for such aldol condensations, that there exists a wide range of alternative methods for the aldol condensation (indicating that such a condensation is not always simple), and that, in many cases, low yields are obtained that involve purifications by recrystallization or column chromatography. To develop a robust standard protocol independent of the nature of the substituents present on the acetophenone or the benzaldehyde involved in the aldol condensation leading to the chalcone, we made a comparison between an aldol condensation in KOH/EtOH and a Wittig reaction between the corresponding ylide and benzaldehyde in water. We describe an improved procedure for the Wittig reaction and a protocol for the elimination of the Ph3P=O byproduct (and the excess of ylide used) by filtration of the crude reaction product through a silica gel plug. We thus demonstrate that such an improved procedure can be a general method for the synthesis of chalcones in high yield and excellent purity and is clearly an improvement on the classical aldol condensation. [ABSTRACT FROM AUTHOR]

Chalcones have a long history of being used for many medical purposes. These are the most prestigious scaffolds in medicine. The potential of Millepachine and its derivatives to treat various malignancies has been demonstrated in this review. The anticancer effects of Millepachine and its derivatives on ovarian cancer, hepatocellular carcinoma, breast, liver, colon, cervical, prostate, stomach, and gliomas are highlighted in the current review. Several genes that are crucial in reducing the severity of the disease have been altered by these substances. They mainly work by preventing tubulin polymerizing. They also exhibit apoptosis and cell cycle arrest at the G2/M phase. Additionally, these compounds inhibit invasion and migration and have antiproliferative effects. Preclinical studies have shown that Millepachine and its derivatives offer exceptional potential for treating a number of cancers. These results need to be confirmed in clinical research in order to develop viable cancer therapies. • The chalcone Millepachine and its derivatives demonstrate anticancer activities in vitro and in vivo. • They primarily act by inhibiting the polymerization of tubulin. • Millepachine and its derivatives showed anticancer potential in various cell lines. [ABSTRACT FROM AUTHOR]

Polyether is a synthetic polymer that has low toxicity and, therefore, it is used in many applications. It can be used as a detergent, emulsifier, drug excipient, pesticide emulsifier, antiseptic, and papermaking additive agent. This study outlines the synthesis, characterization, and fluorescence evaluation of polyethers derived from curcumin analogs. Condensation polymerization of curcumin analogs and dibromoalkanes produces the corresponding polyethers. The Fourier-transform infrared and proton nuclear magnetic resonance spectroscopy confirmed the structures of the newly synthesized polyethers. The thermal stability and solubility of the synthesized polyethers of various solvents were investigated. They showed high stability at high temperatures as thermoplastics. The synthesized polyethers have fluorescent properties in solutions, and the absorption and intensity were dependent on the type of functional groups present in the polymers. The fluorination intensity of polyethers was found to be dependent on the presence of electron-donating groups, the pH of the solution, and the type of solvent used. One of the synthesized polyethers exhibited strong emissive properties at one or two specific wavelengths. [ABSTRACT FROM AUTHOR]

New 4-aryl-2-oxo-6-phenyl-3-cyclohexene-1-carboxamides were obtained by the reaction of N-substituted acetoacetic acid amides with benzalacetophenone and 4-methoxybenzalacetophenone in alcohol in the presence of potassium hydroxide. Structure of the prepared compounds was proved using IR, 1H and 13C NMR spectroscopy, mass spectrometry and X-ray analysis data. [ABSTRACT FROM AUTHOR]

This research article presents the synthesis of a novel series of hybrid analogues of Coumarin-Triazole-Chalcone, which are potential bioactives with a novel mode of action for anticancer therapy. The compounds have been synthesized via aldol condensation and 1,3-dipolar cycloaddition, resulting in the generation of hybrid heterocyclic systems that combine two or more pharmacophores. The synthesized compounds have then been screened for anticancer activity against various human cancer cell lines, including A549 (lung cancer), HeLa (Cervix carcinoma), PANC1 (pancreatic cancer), HT1080 (Fibrosarcoma) and HEK293 (Human embryonic kidney cells), in vitro. One of the compounds, para-nitrile chalcone 9a, demonstrates significant IC50 values in the range of 3.1 to 7.02 µg/mL when compared to the others. All the compounds 9a-d have shown higher IC50 values towards HEK-293 cells indicating their non-toxic nature towards normal cells. Furthermore, in silico approaches have been employed to assess the efficacy of compounds that are active in the MTT assay against molecular targets. The authors conducted docking studies of the proteins PI3K and AKT, which are common target biomarkers in Pancreatic cancer, Lung cancer, Cervical cancer, and Fibrosarcoma, with compound 9a and some known inhibitors. The results show that compound 9a has a good binding affinity with AKT (-10.6) and PI3K (-10.3). However, it is found to be more specific for AKT as its binding site amino acid interactions are similar to those of known AKT inhibitors. These findings provide evidence that hybrid heterocyclic systems may be useful for developing potential bioactives with a novel mode of action for anticancer therapy. [ABSTRACT FROM AUTHOR]

Synthesis of aurones and their derivatives have attracted considerable attention due to their significant biological effects investigated along with their corresponding chalcones against some bacterial as well as fungal strains. Title compound 6-(benzyloxy)-2-[(substitutedphenyl)methylidene]-7-methyl-1-benzofuran-3(2H)-one (2a-i) have been synthesized from 1-[4-benzyloxy-2-hydroxy-3-methyl phenyl]-3-(substituted phenyl)prop-2-en-1-one. The structural assignment of the compounds was based on elemental analysis and IR, 1H NMR, LC Mass, and 13C NMR spectral data. All the synthesized compounds have been screened for their antimicrobial activity to gram-positive and gram-negative bacterial strains and antifungal activity. The antimicrobial activities of the synthesized compounds have been compared with standard drugs like Gentamycin and K. Nystatin. Purity of synthesized compounds has been checked by TLC. [ABSTRACT FROM AUTHOR]

In the last decade, the incidence of obesity has increased dramatically worldwide, reaching a dangerous pandemic spread. This condition has serious public health implications as it significantly increases the risk of chronic diseases such as type 2 diabetes, fatty liver, hypertension, heart attack, and stroke. The treatment of obesity is therefore the greatest health challenge of our time. Conventional therapeutic treatment of obesity is based on the use of various synthetic molecules belonging to the class of appetite suppressants, lipase inhibitors, hormones, metabolic regulators, and inhibitors of intestinal peptide receptors. The long-term use of these molecules is generally limited by various side effects and tolerance. For this reason, the search for natural alternatives to treat obesity is a current research goal. This review therefore examined the anti-obesity potential of natural chalcones based on available evidence from in vitro and animal studies. In particular, the results of the main in vitro studies describing the principal molecular therapeutic targets and the mechanism of action of the different chalcones investigated were described. In addition, the results of the most relevant animal studies were reported. Undoubtedly, future clinical studies are urgently needed to confirm and validate the potential of natural chalcones in the clinical prophylaxis of obesity. [ABSTRACT FROM AUTHOR]

Chalcone is a common simple fragment of natural products with anticancer activity. In a previous study, the research group discovered a series of chalcone derivatives with stronger anticancer activities. To find better anticancer drugs, novel chalcone derivatives A1–A14, B1–B14 have continuously been designed and synthesized. The antiproliferative activity of these compounds against breast cancer cells (MCF-7) was investigated by the Cell Counting Kit-8 (CCK-8) method with 5-fluorouracil (5-Fu) as the control drug. The results showed that compound A14 exhibited excellent antiproliferative ability compared to the control drug 5-Fu. Scratch experiments and cloning experiments further confirmed that compound A14 could inhibit the proliferation and colony formation activity of MCF-7 cells. In addition, molecular docking primarily explains the interaction between compound and protein. These results suggested that compound A14 could be a promising chalcone derivative for further anti-breast cancer research. [ABSTRACT FROM AUTHOR]

The preparation of several azo dyes(2a-h) involved the reaction of 4-aminoacetophenone with sodium nitrite to produce the corresponding diazonium salts, which were then permitted to react with 4-Hydroxycoumarin to produce the relevant azo dye (A). The prepared starting material (A) was then reacted with various substituted benzaldehydes to give a new series of chalcone derivatives(2a-h). Additionally, FT-IR and 1H-NMR spectra used to validate the structures of the newly synthesized compounds. Acid and dispersion dyes are employed with all azo compounds to execute dyeing on multi-fiber strips made of acetate, cotton, nylon, wool, acrylic, and polyester fibers. Each fiber was given moderate to exceptional fastness characteristics by all the synthetic dyes. [ABSTRACT FROM AUTHOR]

Diabetes mellitus is one of the most critical health problems affecting the quality of life of people worldwide, especially in developing countries. According to the World Health Organization reports, the number of patients with diabetes is approximately 420 million, and this number is estimated to be 642 million in 2040. There are 2 main types of diabetes: Type 1 (T1DM), where the body cannot produce enough insulin, and Type 2 (T2DM), where the body cannot use insulin properly. Patients with T1DM are treated with insulin injections while oral glucose‐lowering drugs are used for patients with T2DM. Oral antihyperglycemic drugs used in the treatment of type 2 diabetes mellitus have different mechanisms. Among these, α‐Glucosidase and α‐amylase inhibitors are one of the most important inhibitors. The antidiabetic effect of the chalcones, which show rich activity, draws attention. This research aims to synthesize chalcone derivatives that could show potential antidiabetic activity. In this study, the inhibitory activity of the chalcone compounds (4a‐4g, 5a‐5g) was tested against α‐glucosidase and α‐amylase enzymes. Besides, molecular modeling was utilized to predict potential interactions of the synthesized compounds that exhibit inhibitory effects. In both in vitro and in silico studies, the analyses revealed that compound 5e exhibits strong inhibitory effects against α‐glucosidase enzymes (Binding energy: −7.75 kcal/mol, IC50: 28.88 μM). Additionally, compound 4f demonstrates encouraging inhibitory effects against α‐Amylase (Binding energy: −11.08 kcal/mol, IC50: 46. 21 μM). [ABSTRACT FROM AUTHOR]

Flavonoids are essential substances with antioxidant properties and high medicinal value. Citrus reticulata 'Chachi' peel (CRCP) is rich in flavonoids and has numerous health benefits. The different maturity periods of CRCP can affect the flavonoid contents and pharmacological effects. In this study, we successfully performed UPLC-ESI-MS/MS-based metabolic analysis to compare the metabolites of CRCP at different harvesting periods (Jul, Aug, Sep, Oct, Nov, and Dec) using a systematic approach. The results revealed the identification of a total of 168 flavonoid metabolites, including 61 flavones, 54 flavonols, 14 flavone C-glycosides, 14 dihydroflavones, 9 flavanones, 8 isoflavones, 3 flavanols, 3 dihydroflavonols, and 2 chalcones. Clustering analysis and PCA were used to separate the CRCP samples collected at different stages. Furthermore, from July to December, the relative contents of isoflavones, dihydroflavones, and dihydroflavonols gradually increased and flavanols gradually decreased over time. The relative content of flavonoid C-glycosides showed an increasing and then decreasing trend, reaching the highest value in August. This study contributes to a better understanding of flavonoid metabolites in CRCP at different harvesting stages and informs their potential future utilization. [ABSTRACT FROM AUTHOR]

The aziridination of chalcones with iminoiodinanes under photoredox conditions has been reported. The reaction proceeds through nitrene radical anion intermediate generated from iminoiodinanes. The trapping of nitrene radical anions by chalcones afforded trans‐aziridine products exclusively. The scope of the reaction in terms of both the substrates is considerably wide and in most of the cases trans‐3‐aryl‐aziridine‐2‐ketones were isolated in good yields. The reaction is challenging due to the electron‐deficient nature of the substrate, making this only the second example (after trifluoromethyl alkenes) of photocatalytic aziridination of electron‐deficient double bonds. [ABSTRACT FROM AUTHOR]

Chalcone and triazole scaffolds have demonstrated a crucial role in the advancement of science and technology. Due to their significance, research has proceeded on the design and development of novel benzooxepine connected to 1,2,3-triazolyl chalcone structures. The new chalcone derivatives produced by benzooxepine triazole methyl ketone 2 and different aromatic carbonyl compounds 3 are discussed in this paper. All prepared compounds have well-established structures to a variety of spectral approaches, including mass analysis, 1H NMR, 13C NMR, and IR. Among the tested compounds, hybrids 4c, 4d, 4i, and 4k exhibited exceptional antibacterial susceptibilities with MIC range of 3.59–10.30 μM against the tested S. aureus strain. Compounds 4c, 4d displayed superior antifungal activity against F. oxysporum with MIC 3.25, 4.89 μM, when compared to fluconazole (MIC = 3.83 μM) respectively. On the other hand, analogues 4d, 4f, and 4k demonstrated equivalent antitubercular action against H37Rv strain with MIC range of 2.16–4.90 μM. The capacity of ligand 4f to form a stable compound on the active site of CYP51 from M. tuberculosis (1EA1) was confirmed by docking studies using amino acids Leu321(A), Pro77(A), Phe83(A), Lys74(A), Tyr76(A), Ala73(A), Arg96(A), Thr80(A), Met79(A), His259(A), and Gln72(A). Additionally, the chalcone‒1,2,3‒triazole hybrids ADME (absorption, distribution, metabolism, and excretion), characteristics of molecules, estimations of toxicity, and bioactivity parameters were assessed.

The reaction of (E)-2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-one and (2,4-dinitrophenyl)hydrazine in boiling ethanol containing hydrochloric acid (0.2 mL; 37%) for 1.5 h gave 1-(2,4-dinitrophenyl)-2-(2-(4-fluorobenzylidene)-3,4-dihydronaphthalen-1(2H)-ylidene)hydrazine in a 90% yield. Various spectral analyses, including NMR, and X-ray crystallography established the structure of the newly synthesized hydrazone.

For consumers, the colour presents an indicator that characterizes the quality of the food. As a result of the processes of caramelization of carbohydrates and products of the Maillard reaction, brown compounds are formed with a negative impact on the external appearance of food, which has led to the massive use of synthetic dyes, stable from a technological point of view. The objectives of the European Union foresee the transition to the exclusive use of natural dyes, because synthetic dyes significantly affect the health of the population. Compounds with "azo" type chromophore groups (amaranth, tartrazine) present carcinogenic dangers, being banned in several European countries. The aim of the present study was to evaluate the problem of synthetic dyes and their substitution in food, obtaining, stabilizing and using natural dyes for the food industry. The study highlighted that safflower (Carthamus tinctorius L.) presents a promising source of yellow and red dyes, necessary for use in the food industry, but insufficient information was found regarding the technological properties of safflower petals, the methods of simultaneous extraction of yellow and red dyes and the peculiarities of the use of dyes in the finished product.

Humulus lupulus L. - Hopfen - ist eine seit langem verwendete Arzneipflanze. Die traditionelle Anwendung bei Schlaflosigkeit hängt mit den Bittersäuren zusammen, welche den Hopfen auch für die Brauindustrie wertvoll machen. Mit Hilfe einer aktivitätsgeführten Fraktionierung zur Bestimmung der differenzierungsinduzierenden Aktivität in neuronalen Vorläuferzellen der Maus wurde Xanthohumol C als potentes neuroregeneratives Chalkon identifiziert. Substanzen mit diesem Wirkprofil eignen sich zur Behandlung von neurodegenerativen Erkankungen, welche aufgrund des demogaphischen Wandels eine zunehmende Bürde der westlichen Gesellschaft darstellen. Der Chroman-Ring des Xanthohumol C wurde als wichtiges Strukturmerkmal für die Wirksamkeit identifiziert. Ein auf Cyclodextrinen basiertes Extraktionsverfahren, welches zu einer besser wasserlöslichen und bioverfügbaren Formulierung führt, ebnet den Weg für mögliche phytopharmazeutische Anwendungen des Hopfens im Bereich der Neuroregeneration.

The title compound, C15H14O2, adopts an E configuration about the C=C double bond. The furan ring is inclined to the phenyl ring by 12.03 (9)°. In the crystal, pairs of molecules are linked by C—H...O hydrogen bonds, forming dimers with R22(14) ring motifs. The molecules are connected via C—H...π interactions, forming a three dimensional network. No π–π interactions are observed.

Background: Tuberculosis (TB) is one of the major global health problems and faced to the increased resistance of Mycobacterium tuberculosis strains against existing antitubercular agents, it is important to look for new antitubercular drugs. Aims: The goal of this work was to synthesize four chalcones derivatives from 1-(2'-hydroxyphenyl)-3-(substituted-phenyl)-2-propenone, then evaluate their antitubercular and antifungal activities by standard computational and biological methods. Methods: These chalcones were synthesized by the Claisen-Schmidt condensation and their structures have been determined by Nuclear Magnetic Resonance (NMR 1H and 13C) and Fourier Transform Infrared (FTIR) spectroscopy. The in vitroantimycobacterial and antifungal assays were carried out by the microdilution method against Mycobacterium tuberculosis H37Rv (ATCC 27294), H37Ra (ATCC 25177), and Candida albicans (MTCC 1637), respectively. The molecular docking of these chalcones was performed by AutoDock vina program using Mycobacterial tuberculosis Thymidylate Kinase (PDB ID: 1G3U) and dihydrofolate reductase (PDB ID 1AI9) as target ligand. Results: All synthesized chalcones showed good and moderated antitubercular activity against Mycobacterium tuberculosis H37Rv (virulent strains ATCC 27294), H37Ra (the attenuated strains ATCC 25177) with a range of MICs ranging from 4 to 64 µg/mL. Regarding antifungal activity, all synthesized chalcones were active against Candida albicans strains (MTCC 1637) with a range of MICs ranging from 16 to 128 µg/mL. Based on absorption, distribution, metabolism, and excretion (ADME) properties, all chalcones synthetized satisfied the Lipinski rule. Conclusion: The results suggest that the synthesized chalcones, especially the (E)-3-(4- (dimethylamino) phenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl) prop-2-en-1-one could be used, after in vivo and clinical tests, like antitubercular and antifungal supplement or even replace current drug therapies.

Chalcones are a class of privileged scaffolds with high medicinal significance due to the presence of an α,β-unsaturated ketone functionality. Numerous functional modifications of chalcones have been reported, along with their pharmacological behavior. The present review aims to summarize the structures from natural sources, synthesis methods, biological characteristics against infectious and non-infectious diseases, and uses of chalcones over the past decade, and their structure-activity relationship studies are detailed in depth. This critical review provides guidelines for the future design and synthesis of various chalcones. In addition, this could be highly supportive for medicinal chemists to develop more promising candidates for various infectious and non-infectious diseases.

Renal cyst expansion in polycystic kidney disease (PKD) involves abnormalities in both cyst-lining-cell proliferation and fluid accumulation. Suppression of these processes may retard the progression of PKD. Evidence suggests that the activation of 5' AMP-activated protein kinase (AMPK) inhibits cystic fibrosis transmembrane conductance regulator (CFTR)-mediated chloride secretion, leading to reduced progression of PKD. Here we investigated the pharmacological effects of panduratin A, a bioactive compound known as an AMPK activator, on CFTR-mediated chloride secretion and renal cyst development using in vitro and animal models of PKD. We demonstrated that AMPK was activated in immortalized normal renal cells and autosomal dominant polycystic kidney disease (ADPKD) cells following treatment with panduratin A. Treatment with panduratin A reduced the number of renal cyst colonies corresponding with a decrease in cell proliferation and phosphorylated p70/S6K, a downstream target of mTOR signaling. Additionally, panduratin A slowed cyst expansion via inhibition of the protein expression and transport function of CFTR. In heterozygous Han:Sprague-Dawley (Cy/+) rats, an animal model of PKD, intraperitoneal administration of panduratin A (25 mg/kg BW) for 5 weeks significantly decreased the kidney weight per body weight ratios and the cystic index. Panduratin A also reduced collagen deposition in renal tissue. Intraperitoneal administration of panduratin A caused abdominal bleeding and reduced body weight. However, 25 mg/kg BW of panduratin A via oral administration in the PCK rats, another non-orthologous PKD model, showed a significant decrease in the cystic index without severe adverse effects, indicating that the route of administration is critical in preventing adverse effects while still slowing disease progression. These findings reveal that panduratin A might hold therapeutic properties for the treatment of PKD.

Diabetes mellitus type 2 (T2DM) is a common chronic condition that presents as unsettled hyperglycemia (HG) and results from insulin resistance (IR) and β-cell dysfunction. T2DM is marked by an increased risk of microvascular and macrovascular complications, all of which can be the cause of increasing mortality. Diabetic nephropathy (DNE), neuropathy (DNU), and retinopathy (DR) are the most common complications of diabetic microangiopathy, while diabetic cardiomyopathy (DCM) and peripheral vascular diseases are the major diabetic macroangiopathy complications. Chalcones (CHs) are in the flavonoid family and are commonly found in certain plant species as intermediate metabolites in the biosynthesis of flavonoids and their derivatives. Natural CHs with different substituents exert diverse therapeutic activities, including antidiabetic ones. However, the therapeutic mechanisms of natural CHs through influencing genes and/or signaling pathways in T2DM complications remain unknown. Therefore, this review summarizes the existing results from experimental models which highlight the mechanisms of natural CHs as therapeutic agents for T2DM complications.

Ovarian cancer ranks among the most severe forms of cancer affecting the female reproductive organs, posing a significant clinical challenge primarily due to the development of resistance to conventional therapies. This study investigated the effects of the chalcone derivative 1C on sensitive (A2780) and cisplatin-resistant (A2780cis) ovarian cancer cell lines. Our findings revealed that 1C suppressed cell viability, induced cell cycle arrest at the G2/M phase, and triggered apoptosis in both cell lines. These effects are closely associated with generating reactive oxygen species (ROS). Mechanistically, 1C induced DNA damage, modulated the activity of p21, PCNA, and phosphorylation of Rb and Bad proteins, as well as cleaved PARP. Moreover, it modulated Akt, Erk1/2, and NF-κB signaling pathways. Interestingly, we observed differential effects of 1C on Nrf2 levels between sensitive and resistant cells. While 1C increased Nrf2 levels in sensitive cells after 12 h and decreased them after 48 h, the opposite effect was observed in resistant cells. Notably, most of these effects were suppressed by the potent antioxidant N-acetylcysteine (NAC), underscoring the crucial role of ROS in 1C-induced antiproliferative activity. Moreover, we suggest that modulation of Nrf2 levels can, at least partially, contribute to the antiproliferative effect of chalcone 1C.

4′-dihydrochalcones are secondary metabolites isolated from many medicinal plants and from the resin known as ‘dragon’s blood’. Due to their biological potential, our research objective was to determine the possibilities of using biocatalysis processes carried out in deep eutectic solvents (DESs) to obtain 4′-dihydrochalcones as a model compound. The processes were carried out in a culture of the yeast Yarrowia lipolytica KCh 71 and also in cultures of strains of the genera Rhodotorula and Debaryomyces. Based on the experiments carried out, an optimum process temperature of 35 °C was chosen, and the most suitable DES contained glycerol as a hydrogen bond donor (HBD). For a medium with 30% water content (DES 11), the conversion observed after 24 h exceeded 70%, while increasing the amount of water to 50% resulted in a similar level of conversion after just 1 h. A fivefold increase in the amount of added substrate resulted in a reduction in conversion, which reached 30.3%. Of the other yeast strains tested, Rhodotorula marina KCh 77 and Rhodotorula rubra KCh 4 also proved to be good biocatalysts for the bioreduction process. For these strains, the conversion reached 95.4% and 95.1%, respectively. These findings highlight the potential of yeast as a biocatalyst for the selective reduction of α,β-unsaturated ketones and the possibility of using a DESs as a reaction medium in this process.

This review article is a comprehensive and current overview on chalcones, covering their sources, identification methods, and properties with a particular focus on their applications in the agricultural sector. The widespread use of synthetic pesticides has not only led to increased resistance among weeds and pests, resulting in economic losses, but it has also raised significant health concerns due to the overuse of these chemicals. In line with the European Green Deal 2030 and its Farm to Fork strategy, there is a targeted 50% reduction in the use of chemical pesticides by 2030, emphasizing a shift towards natural alternatives that are more environmentally sustainable and help in the restoration of natural resources. Chalcones and their derivatives, with their herbicidal, fungicidal, bactericidal, and antiviral properties, appear to be ideal candidates. These naturally occurring compounds have been recognized for their beneficial health effects for many years and have applications across multiple areas. This review not only complements the previous literature on the agricultural use of chalcones but also provides updates and introduces methods of detection such as chromatography and MALDI technique.

Context: Metastatic breast cancer is still categorized as an incurable disease because all available therapies are palliative treatments to relieve symptoms and increase life expectancy. Our previous study showed that N-pyrazoline-derived compounds have the potential as an antiproliferative drug in cervical cancer cells line. Therefore, virtual screening is conducted in this study to predict the anticancer potential of several molecules (chalcone and pyrazoline derivatives) against breast cancer cells before in vitro testing. Aims: To screen potential anticancer compounds of chalcone and pyrazoline derivatives through in silico approach. Methods: In this study were carried out multiple virtual screening steps to predict drug-likeness, pharmacokinetic, toxicity, and interactions between drug candidates and receptors involved cell in proliferation (EGFR, PDB.id 7LGS), angiogenesis (VEGFR1, PDB.id 3HNG; VEGFR2, PDB.id 4AG8), and oxidative stress (cytochrome P450, PDB.id 3UA1). Results: Results revealed that pyrazolines A, A1, A2, B, C2, D, and M could potentially be anticancer agents since the molecules qualify Lipinski’s rule, are predicted to have good pharmacokinetics, are indicated as harmless, and exhibit the best binding affinity based on molecular docking analysis. Conclusions: The EGFR appears to be the main pathway targeted by pyrazoline derivates. Meanwhile, the ligand will go through the VEGFR1, VEGFR2, or P450 pathways when it successfully overcomes the binding obstacle. In addition, pyrazolines A, A1, A2, B, C2, D, and M need to be synthesized and evaluated the in vitro and in vivo anticancer activity.

Abstract Ten benzimidazole chalcone derivatives were synthesized, and their monoamine oxidase (MAO) inhibitory activity was evaluated. Most compounds showed higher inhibitory activity against MAO-B than MAO-A. Compound BCH2 exhibited an IC50 value of 0.80 μM, thereby showing the most potent inhibition amongst all. In addition, BCH2 showed the highest MAO-B selectivity index (SI) with an SI value of 44.11 compared to MAO-A. Among the substituents, the halogen group showed the best MAO-B inhibition, and the ortho-position of the B ring showed better inhibitory activity than the para-site. In comparison with ortho-substituents, the inhibitory activity increased in the order, -Cl > -Br > -F > -H. BCH2 was found to be a competitive inhibitor of the enzyme with optimum inhibition kinetics, where Ki was found to be 0.25 ± 0.014 μM. In the reversibility experiment, BCH2 showed a recovery pattern after MAO-B inhibition, similar to that of lazabemide. Thus, BCH2 is a potent, reversible, and selective MAO-B inhibitor and has been suggested as a candidate for the treatment of neurological disorders.

The chalcone structure was introduced into the 4,6-dimorpholinyl-1,3,5-triazine molecule through the C-N bond, and a series of new compounds were obtained. Among them, the pyridyl-containing 6o exhibits anti-proliferation activity similar to that of cisplatin on SW620. Interestingly, the phenyl-containing 6a exhibits a certain selectivity for the anti-proliferation activity of SW620.

Hybrid molecules of pharmacophores could enhance the desired pharmacological activity while minimizing the side effects and drug resistance associated with individual pharmacophores. In this study, we synthesized twelve bis-1,2,3-triazole-based chalcones (78–90 %) yield) in five steps and characterized them via IR, 1H NMR, 13C NMR, and HRMS spectroscopy. Seven hybrid molecules demonstrated good cytotoxicity against A-549 lung cancer cells in the MTT cell viability assay (IC50 = 44.72±0.66 to 86.22±1.06 µM), which is comparable to the IC50 of the anticancer drug doxorubicin (39.86±1.15 µM). Molecular docking studies of the hybrid molecules with extracellular signal-regulated kinase 2/mitogen-activated protein kinase 1 (ERK2) (PDB ID: 4ZXT), which is triggered by lung cancer, showed excellent binding interactions (H-bonding, hydrophobic interactions, halogen bonding, etc.) between the drug candidates and target receptors (binding energy = −7.7 to −9.7 kcal/mol). We believe that these hybrid molecules could have potential applications as anticancer agents.

The pyrazoline scaffold plays a vital role in heterocyclic chemistry as a fundamental building block in both organic and medicinal chemistry. A pyrazoline scaffold is composed of an endocyclic double bond, two nitrogen atoms, and five different types of bonds. It is a significant chemical fragment and exhibits various bioavailabilities, allowing the synthesis of a range of diverse compounds with promising biological potential. Over the past decade, extensive research efforts have been devoted to investigating the therapeutic potentials of pyrazoline scaffolds, encompassing their antibacterial, anti-inflammatory, analgesic, cytotoxic, and anti-tumor activities. Moreover, in the presence of a unique chemical structure, pyrazolines have made it easier to produce new substitutions with low toxicity as compared to their natural analogue. The current review focuses on the recent progress in the synthesis of pyrazoline scaffolds from chalcones, with an emphasis on their possible biological functions. The study identifies a diverse range of pyrazoline derivatives that exhibit promising biological properties and have been successfully reported in various studies. The primary objective is to determine the chemical groups and structural modifications that enhance their bioactivity, low toxicity, and handling. Furthermore, the review explores the bioavailability, synthetic challenges, and progress made in utilising pyrazoline derivatives in pharmaceutical and synthetic chemistry from 2017 to 2023. The different biological potentials of various substituted pyrazolines are reported here such as 1,4-dimethylpiperazine, 2-(2-methyl-1H-benzo[d]imidazol-1-yl)acetohydrazide, 1-methyl-4-phenylpiperazine, 4,5-dihydrooxazole, 2H-chromen-2-one, 2-(4-chlorophenyl)-5-methyl-4,5-dihydrooxazole, benzo[d]thiazole, ethoxybenzene, and 1-bromo-4N,N-dimethylaniline. The review also discusses the effects of different functional groups, such as OCH3, OH, NO2, CF3, and halogens, added to different positions of the pyrazoline scaffold.

The preparation of several azo dyes(2a-h) involved the reaction of 4-aminoacetophenone with sodium nitrite to produce the corresponding diazonium salts, which were then permitted to react with 4-Hydroxycoumarin to produce the relevant azo dye (A). The prepared starting material (A) was then reacted with various substituted benzaldehydes to give a new series of chalcone derivatives(2a-h). Additionally, FT-IR and 1H-NMR spectra used to validate the structures of the newly synthesized compounds. Acid and dispersion dyes are employed with all azo compounds to execute dyeing on multi-fiber strips made of acetate, cotton, nylon, wool, acrylic, and polyester fibers. Each fiber was given moderate to exceptional fastness characteristics by all the synthetic dyes.

Abstract Organic compounds with pyrazole cores have a variety of uses, notably in the pharmaceutical and agrochemical sectors. The interest in creating pyrazole compounds, examining their many features, and looking for potential uses is growing. Our work has concert with synthesis of chalcones and pyrazolines, then finally pyrazoline-aniline derivatives and evaluation their anti-inflammatory, antibacterial and antifungal activities