Synthesis Of Chalcone Derivatives Research Articles

Molecular Docking, Synthesis, Antiproliferative Activity against MCF-7, and In-vitro Alpha Amylase Activities of Newer Generation Pyrimidino Hydroxamic Acid Derivatives

A set of newer generation pyrimidine hydroxamic acid derivatives were designed, synthesized, and evaluated for antiproliferative activity against breast cancer cell line and in-vitro alpha-amylase activity. The design of the molecules was fully dependent upon the structural features of suberoyl anilide hydroxamic acid. Then all the designed molecules (S1-S100) were docked with 4LXZ HDAC2 enzyme and S1, S2, S16 showed good docking interaction scores as compared to SAHA. The interacting residues of (S1, S2, S16) and 4LXZ showed similar amino acid lining as present in the active site. The synthetic procedure of the molecules (S1, S2, S16) was divided into three parts such as synthesis of chalcone derivative using aromatic aldehyde and acetophenone, the reaction between chalcone and thiourea to form substituted pyrimidine-2-thiol, then finally substituted pyrimidine-2-thiol and 2-chloro-N-hydroxyacetamide reacted in the presence of dimethylformamide to obtain the best-docked molecules. All the molecules showed characteristic peaks in fourier-transform infrared (FTIR), proton nuclear magnetic resonance (1H-NMR) and mass spectrometry with sharp melting points and single peak in thin layer chromatography (TLC) plate. Finally antiproliferative activity against MCF-7 and in-vitro alpha amylase activity data confirmed that S1 was the best molecule among all the synthesized molecules.

Synthesis of Chalcone Derivatives as COX-2 Inhibitory Activity for Ischemic Stroke Treatment

Synthesis of Chalcone Derivatives as COX-2 Inhibitory Activity for Ischemic Stroke Treatment

A COMPREHENSIVE REVIEW ON CHALCONE ANALOGUES-VERSATILE SCAFFOLD WITH MEDICINAL AND BIOLOGICAL POTENTIAL

This review’s main focus is on the most recent synthesis of chalcones with N, O, or S heterocycles, highlighting their biological potential. Chalcone derivatives are considered in beneficial species because they possess a keto-ethylenic moiety, CO−CH=CH−. Due to the existence of a reactive α, β-unsaturated carbonyl group, the synthesis of chalcone derivatives, which have been physiologically explored for use against specific disease targets, has been made possible by recent advances in heterocyclic chemistry. The need for novel drugs that are effective against multidrug-resistant pathogens has been driven by the growth in antibiotic resistance brought on by a variety of reasons. Chalcones are phenolic compounds that fall within the flavonoids category. They are a part of a large category of naturally occurring bioactive substances. During this review we have gone through a number of studies where chalcones were created via Claisen Schmidt condensation of suitable acetophenone with suitable aromatic aldehydes in the presence of an aqueous solution of potassium hydroxide and ethanol at room temperature in an effort to create antibacterial agents. The review content have been obtained through web browsing on various scientific databases and search engines like Science Direct, Pub Med, Research Gate, Google Scholar, etc. The synthesis of diverse chalcone derivatives was motivated by the potential activity of naturally occurring chalcones as anticancer, anti-inflammatory, antibacterial, antioxidant, and antiparasitic characteristics, as well as by their unique chemical structural structure. Flavonoids and isoflavonoids, which are frequent chemical building blocks found in a variety of naturally derived compounds, are enhanced by chalcone. This review may prove to be helpful for the creation and design of new powerful therapeutic medications.

Synthesis of chalcone derivatives with methoxybenzene and pyridine moieties as potential antimalarial agents

Malaria remains an endemic disease in tropical regions, urgently needed the search for effective antimalarial agents due to resistance against existing drugs. This study investigated the potential antimalarial activity of pyridine-based chalcone derivatives against P. falciparum 3D7 and FCR3 strains. The chalcones were synthesized through a one-pot method using various pyridine carbaldehyde, resulting in yields ranging from 53.74 to 86.37%, and all products were characterized using FTIR, GC-MS, and NMR spectroscopies. Among the six chalcones tested, chalcone A [1-(2-methoxyphenyl)-3-(pyridin-2-yl)prop-2-en-1-one] displayed the highest antimalarial activity with IC50 values of 0.48 and 0.31 μg/mL against P. falciparum 3D7 and FCR3 strains, respectively, and a resistance index of 0.65. Molecular docking studies highlighted the interaction of the carbonyl group of all chalcones with Asn108 amino acid residue in the PfDHFR-TS active site via hydrogen bonding, demonstrating their potential as the antimalarial agent. Notably, the positioning of methoxy and pyridine substituents significantly influenced the antimalarial activity of the chalcones.

Synthesis of Chalcone Derivatives and its Anti- Microbiological Activities

Chalcones are organic substances that are naturally found in plants, especially those in the Fabaceae family. fused aromatic rings connected by a 3-C unsaturated carbonyl system make up the chemical building blocks of their basic chemical composition. Chalcones are biologically active in a variety of ways, including as antioxidants, anticancer agents, anti- inflammatory agents, antibacterial agents, and antiviral agents. Scavenging free radicals,inducing cancer cell apoptosis, obstructing the proliferation and division of cancerous cells, and lowering inflammation by preventing the manufacturing of interleukins and enzymes are all abilities of these substances. Also, it has been discovered that chalcones contain antibacterialand antiviral properties that prevent the growth of a variety of bacteria, fungi, and viruses as well as their replication.

Synthesis of Chalcone Derivatives and its Antimicrobial Activities

Synthesis of Chalcone Derivatives and its Antimicrobial Activities

Synthesis of chalcone derivatives by Claisen-Schmidt condensation and in vitro analyses of their antiprotozoal activities

Chalcone is a molecule with known biological activities. Based on this, a series of chalcone derivatives bearing methyl, phenyl or furanyl substituents at different positions of A and B rings were synthesised, characterised, and evaluated regarding antiprotozoal activity. Molecules were synthesised via base catalyzed Claisen-Schmidt condensation and characterised by IR and NMR spectral data. Antiprotozoal activity against Phytomonas serpens, Leishmania amazonensis and Acanthamoeba polyphaga was performed. All compounds inhibited more than 50% of the growth of P. serpens while five had this effect on L. amazonensis and all of them no more than 35% of inhibition on A. polyphaga. Remarkably interesting antiprotozoal effects were recorded with compound 5, with IC50 of 1.59 µM for P. serpens and 11.49 µM for L. amazonensis. The addition of a naphthyl group to the B ring can be postulated to be the cause of the 10 times increase observed in its trypanocidal activity.

Synthesis of Chalcone Derivatives from Halogenated Vanillin and their Activity Test as Antioxidant

Synthesis of 3-chloro-4-hydroxy-5-methoxybenzaldehyde, 3-bromo-4-hydroxy-5-methoxybenzaldehyde and 2',4'-dihydroxy-3-bromo-4-hydroxy-5-methoxyhalcone and evaluation of their antioxidant activity have been carried out. 3-Chloro-4-hydroxy-5-methoxybenzaldehyde was obtained through chlorination of vanillin using Ca(ClO)2, while 3-bromo-4-hydroxy-5-methoxybenzaldehyde was obtained via bromination of vanillin using KBrO3 in glacial acetic acid solvent and 47% HBr catalyst. Then, 2',4'-dihydroxy-3-bromo-4-hydroxy-5-methoxychalcone was prepared from 3-bromo-4-hydroxy-5-methoxybenzaldehyde and 2-4-dihydroxyacetophenone through Claisen-Schmidt condensation in the presence of KOH (40%) base and KSF montmorillonite in methanol. Elucidation of the structure of these compounds was performed using FTIR, GC-MS, TLC-Scanner, MS-Direct, 1H-NMR, and 13C-NMR. The synthesized benzaldehydes and chalcone were tested for their antioxidant activities using DPPH method, where 2,6-di-tert-butyl-4-methylphenol (BHT) was used as positive control. The results showed that 3-chloro-4-hydroxy-5-methoxybenzaldehyde, 3-bromo-4-hydroxy-5-methoxybenzaldehyde and 2',4'-dihydroxy-3-bromo-4-hydroxy-5-methoxyhalcone were obtained in 53%, 97%, and 1%, respectively. The antioxidant activity assay showed that BHT, 3-chloro-4-hydroxy-5-methoxybenzaldehyde, 3-bromo-4-hydroxy-5-methoxybenzaldehyde and 2',4'-dihydroxy-3-bromo-4-hydroxy-5-methoxyhalcone displayed the IC50 of 27.94, 244.11, 269.44 and 162.10 µg/mL, respectively.

An Efficient Synthesis of α, β Unsaturated Ketones via Claisen-schmidt Condensation Reaction using Amino Acid Based Ionic Liquids

: Synthesis of chalcone by Claisen–Schmidt condensation using recyclable L- aspartic acid coupled with imidazolium-based ionic liquid as a green synthetic approach has been developed. Present work offers significant advantages, such as high yield, enhanced reaction speed even at room temperature, catalyst reusability, and the involvement of non-toxic reagents. Background: Chalcones belong to the flavonoid family and possess pharmacological and biological activities, including antibacterial, antifungal, immunosuppressive, and anti-nociceptive properties. Objective: Ionic liquids have emerged as powerful tools for molecular organic solvents. Their wide liquid range, easy recovery, and reusability make them a greener alternative to volatile organic solvents. Thus, in the present work, our objective was to employ them as dual catalysts and solvent systems for the synthesis of chalcone via the CS condensation. Methods: In a typical experiment, benzaldehyde (10 mmol), acetophenone (10 mmol), and 2.5 mol% (L-AAIL) ionic liquid were mixed in a 50 mL round-bottom flask. The reaction was proceeded quickly at room temperature with stirring, and the resulting mixture became a biphasic system with the precipitate at the bottom and the upper phase containing some unreacted substrate which was separated from the catalyst by filtration and decantation. The catalyst was extracted with CH2Cl2 and separated for the next cycle. Results: Claisen–Schmidt condensation accomplished with reasonable to good yields, ranging from 78 to 95% at room temperature in presence of the [L-AAIL], as compared to the traditional route at more than 100°C. Conclusion: [L-AAIL] is found a highly efficient and eco-friendly catalyst for the synthesis of chalcone derivatives at room temperature. [L-AAIL] as a solvent and catalyst will exhibit real advantages by providing a ‘green’ process with a safer operation. Furthermore, short reaction periods, mild reaction conditions, easier separation, and reusability of ionic liquid made this methodology valuable for synthetic organic chemists as well as industry.

Synthesis of Chalcone Derivative from Clove Leaf Waste as a Natural Antioxidant

Synthesis of Chalcone Derivative from Clove Leaf Waste as a Natural Antioxidant

A new method for the synthesis of chalcone derivatives promoted by PPh3/I2under non-alkaline conditions

A straightforward and general method has been developed for the synthesis of chalcone derivatives by a Claisen-Schmidt reaction in the presence of PPh3/I2 in 1,4-dioxane under reflux temperatures. With the condensation of the aromatic ketone and aldehyde occurring at non-strongly alkaline conditions, our proposed method significantly expands the range of applicable substrates, especially for groups that are unstable under alkaline conditions.

One-pot synthesis of spirooxindole-pyrrolizidine compounds using magnetically separable Fe3O4-graphene oxide (Fe3O4-GO) catalyst

A couple of novel Spirooxindole-pyrrolizidine compounds have been synthesized from chalcone derivatives as α, β-unsaturated carbonyl compounds by the help of heterogeneous magnetically separable Fe3O4-GO catalyst. Four steps involved in this research are synthesis of Fe3O4-GO catalyst, synthesis of chalcone derivatives from 4-hydroxybenzaldehyde and cinnamaldehyde, synthesis of spirooxindole-pyrrolizidine derivatives by 1,3-dipolar-cycloaddition reaction through the formation of azomethine ylide, and the last is antioxidant activity assay using DPPH method. The result showed that the use of Fe3O4-GO catalyst as much as 5 wt% can increase the reaction yield to 86.27 %. From the DPPH assay, it is known that spirooxindole-pyrrolizidine derivatives have an antioxidant activity but spirooxindole-pyrrolizidine derived from 4-hydroxybenzaldehyde is the better one.

Synthesis of Chalcone Derivatives and Studies on Their Inhibitory Activity and Molecular Docking

Synthesis of Chalcone Derivatives and Studies on Their Inhibitory Activity and Molecular Docking

Synthesis of Chalcone Derivatives: Inducing Apoptosis of HepG2 Cells via Regulating Reactive Oxygen Species and Mitochondrial Pathway.

Chalcone derivatives, as a hot research field, exhibit a variety of physiological bioactivities and target multiple biological receptors. Based on the skeleton of (E)-1,3-diphenyl-2-propene-1-one, 14 chalcone derivatives were designed and synthesized, and evaluated as the antitumor candidates agents against four human cancer cell lines (A549, Hela, HepG2, and HL-60) as well as one normal cell line (WI-38). Among the title compounds, compound a14 showed better inhibitory activity against HepG2 cells (IC50 = 38.33 µM) and had relatively weak cytotoxicity towards normal cells WI-38 (IC50 = 121.29 µM). In this study, apoptosis, cycle arrest, assessment of reactive oxygen species (ROS) level, and measurement of mitochondrial membrane potential were adopted to explore the inhibitory mechanism of a14 towards HepG2. Compound a14 could effectively block the division of HepG2 cell lines in the G2/M phase and robustly induced generation of ROS, demonstrating that the generation of ROS induced by a14 was the main reason for resulting in the apoptosis of HepG2 cells. Moreover, the mitochondrial membrane potential (MMP) of HepG2 cells treated with a14 was significantly decreased, which was closely related to the enhanced ROS level. Furthermore, based on Western blot experiment, cell apoptosis induced by a14 also involved the expression of B-cell lymphoma-2 (Bcl-2) family and Caspase 3 protein. In summary, compound a14 could contribute to the apoptosis of HepG2 cells through regulating ROS-mitochondrial pathway, which provides valuable hints for the discovery of novel anti-tumor drug candidates.

Synthesis Chalones and Their Isomerization into Flavanones and Azaflavanones.

Flavanones [2-aryl-2,3-dihydrochromen-4(1H)ones] and 2-aryl-2,3-dihydroquinolin-4(1H)-ones are valuable precursors in the synthesis of important pharmacological scaffolds, so efficient methodologies towards their synthesis are important in the medicinal chemistry context. Their synthesis also involves theoretical concepts such as aldol condensation, isomerization, and catalysis that make it useful in an undergraduate organic chemistry laboratory. The use of both microwave irradiation as a source of energy to promote reactions and efficient catalysts are considered within green chemistry principles, mostly because the reaction yields are improved and reaction time decreased. In this paper, the efficiency of microwave irradiation use in the synthesis of chalcone derivatives and efficient catalyst systems to promote their isomerization into flavanones and 2-aryl-2,3-dihydroquinolin-4(1H)-ones is demonstrated.

Synthesis of Chalcone Derivatives and Their <i>in vitro</i> Anticancer Test Against Breast (T47D) and Colon (WiDr) Cancer Cell Line

The synthesis of chalcone derivatives as target compounds and anticancer test against breast (T47D) and colon (WiDr) cell line had been performed. The synthesis was performed by Claisen-Schmidt condensation by using acetophenone and benzaldehyde derivatives. The anticancer activity test of chalcone derivatives was carried out by MTT assay against T47D and WiDr cell lines. The synthesis was started by reacting 4-hydroxyacetophenone and benzaldehyde derivatives such as p-anisaldehyde (chalcone A [(E)-4'-hydroxy-4-methoxychalcone]), veratraldehyde (chalcone B [(E)-4'-hydroxy-3,4-dimethoxychalcone]), 4-chlorobenzaldehyde (chalcone C [(E)-4'-hydroxy-4-chlorochalcone]) and 2,4-dihydroxyacetophenone with 4-chlorobenzaldehyde (chalcone D [(E)-2',4'-dihydroxy-4-chlorochalcone]) in methanol as solvent. The synthesis was carried out in alkaline condition (KOH) by stirring the mixture at room temperature for 48 h. The structures of products were identified by FTIR, GC-MS, 1H- and 13C-NMR spectrometers. The results showed that the chalcone derivatives (A-D) were yielded in 96; 97; 96; and 93%, respectively as yellow solid. The anticancer test indicated that the chalcone D was the most active towards T47D cell line with IC50 of 42.66 μg/mL and the chalcone C was the most active against WiDr cell line with IC50 of 20.42 μg/mL.

Design and synthesis of chalcone derivatives as potential non-purine xanthine oxidase inhibitors.

BackgroundBased on some previous research, the chalcone derivatives exhibited potent xanthine oxidase inhibitory activity, e.g. sappanchalcone (7), with IC50 value of 3.9 μM, was isolated from Caesalpinia sappan. Therefore, objectives of this research are design and synthesis of 7 and other chalcone derivatives by Claisen–Schmidt condensation and then evaluate their XO inhibitory activity.ResultsFifteen chalcone derivatives were synthesized by Claisen–Schmidt condensation, and were evaluated for XO inhibitory activity. Nine out of 15 synthetic chalcones showed inhibitory activity (3; 5–8; 10–13). Sappanchalcone derivatives (11) (IC50, 2.5 μM) and a novel chalcone (13) (IC50, 2.4 μM) displayed strong xanthine oxidase inhibitory activity that is comparable to allopurinol (IC50, 2.5 μM). The structure–activity relationship of these chalcone derivatives was also presented.ConclusionsIt is the first research on synthesis sappanchalcone (7) by Claisen–Schmidt condensation. The overall yield of this procedure was 6.6 %, higher than that of reported procedure (4 %). Design, synthesis, and evaluation of chalcone derivatives were carried out. This result suggests that the chalcone derivative can be used as potential non-purine XO inhibitors.Graphical abstractThe chalcone derivatives as potential non-purine xanthine oxidase inhibitors Electronic supplementary materialThe online version of this article (doi:10.1186/s40064-016-3485-6) contains supplementary material, which is available to authorized users.

Synthesis of Chalcone Derivatives and Their Effects on Proliferation and Tubulin Dynamics Instability of HT-29 Cells

Synthesis of Chalcone Derivatives and Their Effects on Proliferation and Tubulin Dynamics Instability of HT-29 Cells

Synthesis of Chalcone Derivatives and Evaluation Their Biological Activities

Synthesis of Chalcone Derivatives and Evaluation Their Biological Activities

Design and synthesis of chalcone derivatives as potent tyrosinase inhibitors and their structural activity relationship

Browning of fruits and vegetables is a serious issue in the food industry, as it damages the organoleptic properties of the final products. Overproduction of melanin causes aesthetic problems such as melisma, freckles and lentigo. In this study, a series of chalcones (1–10) have been synthesized and examined for their tryrosinase inhibitory activity. The results showed that flavokawain B (1), flavokawain A (2) and compound 3 were found to be potential tyrosinase inhibitors, indicating IC50 14.20–14.38μM values. This demonstrates that 4-substituted phenolic compound especially at ring A exhibited significant tyrosinase inhibition. Additionally, molecular docking results showed a strong binding affinity for compounds 1–3 through chelation between copper metal and ligands. The detailed molecular docking and SARs studies correlate well with the tyrosinase inhibition studies in vitro. The structures of these compounds were elucidated by the 1D and 2D NMR spectroscopy, mass spectrometry and single X-ray crystallographic techniques. These findings could lead to design and discover of new tyrosinase inhibitors to control the melanine overproduction and overcome the economic loss of food industry.