Bis-chalcone Derivatives Research Articles

Bis-chalcones obtained via one-pot synthesis as the anti-neurodegenerative agents and their effect on the HT-22 cell line

In the area of research on neurodegenerative diseases, the current challenge is to search for appropriate research methods that would detect these diseases at the earliest possible stage, but also new active structures that would reduce the rate of the disease progression and minimize the intensity of their symptoms experienced by the patient. The chalcones are considered in the context of candidates for new drugs dedicated to the fight against neurodegenerative diseases. The synthesis of bis-chalcone derivatives (3a-3d), as aim molecules was performed. Their structures were established by applying 1H NMR, 13C NMR, MS, FT-IR and UV–Vis spectra. All bis-chalcones were synthesized from terephthalaldehyde and appropriate aromatic ketone as substrates in the Claisen-Schmidt condensation method and evaluated in the biological tests and in silico analysis. Compounds exerted antioxidant activity using the HORAC method (3a-3d) and decreased the activities of GPx, COX-2 (3b-3d), GR (3a-3c) and CAT (3a,3b). The high anti-neurodegenerative potential of all four bis-chalcones was observed by inhibition of acetyl- (AChE) and butyrylcholinesterase (BChE) and a positive effect on the mouse hippocampal neuronal HT-22 cell line (LDH release and PGC-1α, PPARγ and GAPDH protein expression). TD-DFT method (computing a number of descriptors associated with HOMO–LUMO electron transition: electronegativity, chemical hardness and potential, first ionization potential, electron affinity) was employed to study the spectroscopic properties. This method showed that the first excited state of compounds was consistent with their maximum absorption in the computed UV–Vis spectra, which showed good agreement with the experimental spectrum using PBE1PBE functional. Using in silico approach, interactions of bis-chalcones with selected targets (aryl hydrocarbon receptor (AhR) PAS-A Domain, ligand binding domain of human PPAR-γ, soman-aged human BChE-butyrylthiocholine complex, Torpedo californica AChE:N-piperidinopropyl-galanthamine complex and the COX-2-celecoxib complex) were characterized. Results obtained in in silico models were consistent with in vitro experiments.

Conducting Behavior of Bischalcone Derivatives

With the scope of bischalcone-based copolyesters can be used as semiconductors; two copolyesters were synthesized by the solution polycondensation method. The Bischalcone diol was analyzed by UV-Visible, FTIR, NMR (1H, 13C NMR) spectroscopy. Using the UV-Visible data, the bandgap energy of the Bischalcone diol was calculated and found to be 2.82 eV. The Physico-chemical properties like Inherent viscosity and refractive index of the copolyesters were determined. Spectral studies such as FTIR, 1H and 13C NMR spectroscopy. The thermal property of the copolyesters was analyzed by differential scanning calorimetry. The melting temperature of the PTMI is observed at 320°C, and PTMT exhibits 360°C. The PTMT shows higher stability than the PTMT copolyester. The highest ionic conductivity for PTMI is 3.50 x 10-4 (S cm-1). The PTMT copolyester shows -0.0035 KJ mol-1 whereas the PTMI copolyester shows 0.0005 KJ mol-1. The electrochemical impedance analysis and conductivity measurement were examined for the two copolyesters expecting semi-conducting behavior which can be a good candidate for the optoelectronics application.

Metal Complexation of Bis-Chalcone Derivatives Enhances Their Efficacy against Fusarium Wilt Disease, Caused by Fusarium equiseti, via Induction of Antioxidant Defense Machinery.

Sweet pepper (Capsicum annuum L.) is one of the most widely produced vegetable plants in the world. Fusarium wilt of pepper is one of the most dangerous soil-borne fungal diseases worldwide. Herein, we investigated the antifungal activities and the potential application of two chalcone derivatives against the phytopathogenic fungus, Fusarium equiseti, the causal agent of Fusarium wilt disease in vitro and in vivo. The tested compounds included 3-(4-dimethyl amino-phenyl)-1-{6-[3-(4 dimethyl amino-phenyl)-a cryloyl]-pyridin-2-yl}-propanone (DMAPAPP) and its metal complex with ruthenium III (Ru-DMAPAPP). Both compounds had potent fungistatic activity against F. equiseti and considerably decreased disease progression. The tested compounds enhanced the vegetative growth of pepper plants, indicating there was no phytotoxicity on pepper plants in greenhouse conditions. DMAPAPP and Ru-DMAPAPP also activated antioxidant defense mechanisms that are enzymatic, including peroxidase, polyphenole oxidase, and catalase, and non-enzymatic, such as total soluble phenolics and total soluble flavonoids. DMAPAPP and Ru-DMAPAPP also promoted the overexpression of CaCu-SOD and CaAPX genes. However, CaGR and CaMDHAR were downregulated. These results demonstrate how DMAPAPP and Ru-DMAPAPP could be employed as a long-term alternative control approach for Fusarium wilt disease as well as the physiological and biochemical mechanisms that protect plants.

Synthesis and Characterization of some New 3,3'-(1,4-Phenylene) Bis (1-(4-Aminophenyl) Prop-2-en-1-one) Amide Derivatives

A new amide derivative series [A1-A8] was prepared in good yield by direct reflux condensation of bis-chalcone [3,3'-(1,4-phenylene) bis (1-(4-aminophenyl) prop-2-en-1-one)] with different carboxylic acids and acrylamide in the presence of a suitable solvent and amount of sodium hydroxide (NaOH). The structures of the synthesized amide were characterized by various spectral techniques, including FTIR (Fourier-Transform Infrared Spectroscopy), 1H-NMR (Proton Nuclear. Magnetic Resonance Spectroscopy), and mass spectroscopy, and the resultant spectra confirmed the expected structure of the prepared bis-chalcone derivative.

In vitro Screening for Antioxidant and Antimicrobial Properties of 3,5-Bis(E-thienylmethylene) piperidin-4-one, a Curcumin Analogue

Pharmacognosy Research,2022,14,3,276-283.DOI:10.5530/pres.14.3.40Published:July 2022Type:Original ArticleAuthors:Jayaseelan Nivedha, Kaliyamoorthi Kanimozhi, Subashchandrabose Olikkavi, T. Vidhyasagar, Natesan Vijayakumar, Chinnaiyan Uma, K. Rajeswari, and Lakshmanan Vennila Author(s) affiliations:Jayaseelan Nivedha1, Kaliyamoorthi Kanimozhi1, Subashchandrabose Olikkavi1, T. Vidhyasagar2, Natesan Vijayakumar1, Chinnaiyan Uma4, K. Rajeswari2,3, Lakshmanan Vennila1,* 1Department of Biochemistry and Biotechnology, Annamalai University, Chidambaram, Tamil Nadu, INDIA. 2Department of Chemistry, Annamalai University, Chidambaram, Tamil Nadu, INDIA. 3Department of Chemistry, GAC-CDM, Chidambaram, Tamil Nadu, INDIA. 4Department of Microbiology, Annamalai University, Chidambaram, Tamil Nadu, INDIA. Abstract:Background: Curcumin is a naturally occurring bis-chalcone derivative in the commonly used Indian spice turmeric and is well-known for its potent chemopreventive, anti-angiogenic, anti-cancer properties. 3,5-bis[(E)-thienylmethylene] piperidin-4-one (BTMP) is the newly synthesised synthetic analogue of curcumin that is tested for its antioxidant and antimicrobial properties in vitro. Objectives: This study was to determine the antioxidant activity and antibacterial potentials of newly synthesised analogues of curcumin viz., 3,5-bis[(E)- thienylmethylene] piperidin-4-one (BTMP), was examined in vitro. Materials and Methods: BTMP was evaluated for its antioxidant and antimicrobial using 1,1-diphenyl-2-picryl hydroxyl (DPPH•) radical scavenging assay, 2,2’-azinobis3-ethyl benzothiazoline-6-sulfonic acid (ABTS•+), ferric reducing antioxidant power (FRAP), nitric oxide scavenging assay, superoxide anion radical scavenging assay (O2•−), hydrogen peroxide scavenging, reducing ability assay, metal ion chelating and phosphomolybdenum assays. Results: 40μg/ml of BTMP showed higher antioxidant activity than the other three doses due to its highest free radical scavenging ability at this particular dose. All doses of BTMP showed antimicrobial activity against E. coli and S. aureus. 40μg/ml of BTMP showed the highest zone of inhibition against both tested pathogens. Conclusion: The introduction of basic functionality and the presence of exocyclic double bonds of BTMP has significantly contributed to the antioxidant activity and antimicrobial activity against both gram-positive and gram-negative bacteria. Keywords:Antibacterial, Antioxidant, Curcumin, DPPH, Reducing abilityView:PDF (361.28 KB)

Bio-Evaluation of 99mTc-Labeled Homodimeric Chalcone Derivative as Amyloid-β-Targeting Probe.

Chalcone derivatives have been successfully utilized for a range of biological applications and can cross the blood–brain barrier easily. β-amyloid-specific bis-chalcone derivative, 6,9-bis(carboxymethyl)-14-(4-[(E)-3-(4-(dimethylamino)phenyl)acryloyl]phenoxy)-3-(2-[(2-(4-[(E)-3-(4-(dimethylamino)phenyl)acryloyl]phenoxy)ethyl)amino]-2-oxoethyl)-11-oxo-3,6,9,12-tetraazatetradecanoic acid, DT(Ch)2, was analyzed using molecular modeling to explain the binding modes of the ligand with amyloid fibril and monomer followed by 99mTc-complexation in 95% yield and 98.7% efficiency. High-binding specificity of the radiocomplex was established following in vitro evaluation against 100-fold excess of DT(Ch)2. 99mTc–DT(Ch)2 exhibited <3% trans-complexation in human serum after 24 h, indicating high stability. A fast clearance rate in pharmacokinetics studies displayed a biphasic pattern with t1/2(F) = 30 min ± 0.09 and t1/2(S) = 4 h 20 min ± 0.06. In vivo single-photon emission computed tomography (SPECT) imaging in rabbits reiterated the pharmacokinetics data with initially high brain uptake followed by rapid washout. Biodistribution studies confirmed the initial brain uptake as 1.16 ± 0.02% ID/g after 2 min and the brain2min/brain30min ratio was 3.74. Radioactivity distribution in the brain was >40% in the cingulate cortex followed by >25% in the hippocampus, a distribution pattern aligned to Alzheimer’s affected brain regions. Radiocomplex also displayed rapid plasma clearance followed by hepatobolic and renal modes of excretion.

Controlled drug release characteristics and antibacterial influence of streptomycin sulfate-loaded PMMA/PEO/bis-chalcone derivatives-based fibers

The aim of this study is to fabricate streptomycin sulfate (STM)-loaded bis-chalcone/poly(methyl methacrylate) (PMMA)/poly(ethylene oxide) (PEO) based fiber mats for drug delivery and antibacterial applications. This study presents the synergetic effect of a bis-chalcone derivatives ((2E,6E)‐2,6–bis[(thiophen‐2–yl)methylene]cyclohexanone (BTC) or (2E,6E)‐2,6–bis(4-nitrobenzylidene)cyclohexanone (BNC)) to STM loading and antibacterial properties of fibers. Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy and energy-dispersive X-ray spectroscopy (SEM/EDS) were employed to characterize diverse features of the prepared electrospun fibers, namely, morphology, elemental composition, structures of the molecular chains. The longest drug release profile was observed for PMMA/PEO/BTC-STM60 fiber (77.6% for 33,120 min) compared to the other fiber samples. According to the drug release results, PMMA/PEO/BTC-STM60 is the most preferable electrospun fiber to provide a prolonged release for 33,120 min rather than the immediate release of STM. The antibacterial effects of drug-containing and non-drug fibers against Bacillus cereus and Escherichia coli were investigated. It was observed that the drug-free fibers did not have any antibacterial effect, while the drug-containing fibers completely inhibited the growth of B. cereus and E. coli. Our findings can provide insight into new fibers prepared with antimicrobial compounds for drug release based wound dressing applications.

Synthesis, in vitro and in silico antitumor evaluation of 3-(2,6-dichlorophenyl)-1,5-diphenylpentane-1,5‑dione: Structure, spectroscopic, RDG, Hirshfeld and DFT based analyses

New bischalcone derivative 3-(2,6-dichlorophenyl)-1,5-diphenylpentane-1,5‑dione (C23H18Cl2O2) has been efficiently synthesized and the solid state formation of the grown crystals was characterized by X-ray crystallographic diffraction (XRD)analysis at 296 K. The single crystal XRD results show that the title compound belongs to triclinic system with unit cell dimensions, a = 9.4104 (12) (Å), b = 10.2951(13) (Å), c = 10.9411(15) (Å) and V = 980.9(Å3). The key contributor intermolecular interactions C‒O···H/H···O‒C were explored by Hirshfeld surface analysis. The active functional group interpretations have been carried using FT-IR and FT-Raman spectroscopies with the assistance of energy distributions. Density functional theory (DFT) calculations of the synthesized compound carried out for better understanding of molecular futures. Hyperconjugative interactions present in the molecule were also quantified using natural bond orbitals (NBO). Reactivity and stability of the title molecule assessed utilizing global reactivity descriptors. The condensed Fukui functions explored the available electrophile and nucleophile regions in the form of local based descriptors. The reduced density gradient (RDG) isosurfaces reveals the dominance of non-bonded interactions of the title compound. MTT assay revealed that the title compound had potentiate antitumor activity against human lung cancer A549 cells with 40.71 µg/mL IC50 value. Moreover the capability of the compound to be interconnected within the key amino acids of lung cancer receptor binding sites was detected by molecular docking. Antibacterial and antifungal efficacy of the title compound studied using Kirby-Bauer disc diffusion technique.

Design, synthesis and biological evaluation of novel bischalcone derivatives as potential anticancer agents

Building on our previous work that discovered chalcone as a promising pharmacophore for anticancer activity, we have various other chalcone derivatives and have synthesized a series of novel bischalcone to explore their anticancer activity. Among all tested compounds, compounds 6a, 6b, and 6c showed the highest antiproliferative activity against A-549 cancer cell lines with the average IC50 values of 4.18, 4.52, and 5.05 µM, respectively. Moreover, compound 6c showed high antiproliferative activity against the Caco-2 cell line; thus, it was 2- and 4-fold more active than the reference compounds, i.e., methotrexate and capecitabine. Compound 6a also induced cell-cycle arrest in the S phase, whereas compounds 6b and 6c were observed to stop at the G0/G1 phase. Thereafter, we evaluated that compound 6c also had the highest apoptosis/necrosis ratio than other compounds and the standard compound. The anticancer property of the 6c was also supported by molecular docking studies carried out on the EGFR and HER2 receptors. Overall, we expect that these compounds can be further developed for the potential treatment of lung cancer.

Bis-chalcone derivatives derived from natural products as near-UV/visible light sensitive photoinitiators for 3D/4D printing

Four series of novel bis-chalcone compounds with excellent performances have been synthesized and examined for the first time as photoinitiators in combination with an amine and an iodonium salt for the FRP of acrylates and the CP of EPOX.

Acidochromic Behavior of Dibenzylidene Cyclohexanone-Based Bischalcone: Experimental and Theoretical Study.

Synthesis and characterization of substituted 2,6-dibenzylidene cyclohexanone-based bischalcone derivatives and their optimized geometries were investigated by density functional theory. The synthesized compounds were identified through ultraviolet–visible, Fourier transform infrared, and 1H nuclear magnetic resonance spectroscopies and elemental analysis. Significant acidochromic behavior was observed for 2,6-bis(4-dimethylamino-benzylidene)-cyclohexanone 1e. This result is owing to the preferential protonation of the chromophoric N,N-dimethylamino group, that is, quaternary salt formation and deactivation of the resonance system. The result was consistent with computational studies where the protonation was favored by 211 kcal/mol in the gas phase. The compounds also showed solvatochromic behavior. The geometries of the synthesized compounds were optimized with B3LYP/6-311G+(d,p) and APFD/6-311+G(d,p) basis sets. The single point energy indicated that APFD/6-311+G(d,p) basis set gave the lowest energy of 445–655 kcal/mol for the studied bischalcone derivatives. Quantum chemical parameters were also calculated.

Bis-Kalkon Türevlerinin Elektrokimyasal Davranışlarının İncelenmesi

The electrochemical behavior of (2E,5E)-2,5-dibenzylidenecyclopentanone (P1) and (2E,5E)-2,5-bis(4-nitrobenzylidene)cyclopentanone (P2) known as bis-chalcone derivatives was studied by cyclic voltammetry (CV) using an indium tin oxide (ITO) as the working electrode. Repeated cyclic voltammograms measurements exhibited excellent long-term redox stability for bis-chalcone derivatives. The oxidation peak for in the anodic region for the 1st cycle of the P1 appeared at -0.20 V, while the oxidation peak of P2 was observed at -0.47 V. On the other hand, the existence of the electron attracting NO2 group at p-position on the benzene ring in the structure of P2 caused an increase in the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy gap. The surface morphology and structural features of P1 and P2 films coated onto ITO glass substrates were investigated by using scanning electron microscopy (SEM) and energy-dispersive X-ray spectroscopy (EDS). SEM micrographs demonstrated that the P1 and P2 were homogeneously distributed over the ITO surface. After CV measurement, it was observed that the grain size of P2 increased with increasing ITO surface roughness. Moreover, the EDS results confirmed the presence of P1 and P2 on the ITO surface.

Biological evaluation of non-basic chalcone CYB-2 as a dual ABCG2/ABCB1 inhibitor

The enhancement of drug efflux caused by ATP-binding cassette (ABC) transporters (including ABCG2 and ABCB1) overexpression is an important factor for multidrug resistance (MDR) in cancers. After testing the reversal activities of 19 chalcone and bis-chalcone derivatives on MDR cancer cell lines, we found that non-basic chalcone CYB-2 exhibited the most potent reversal activities against both ABCG2- and ABCB1-mediated MDR. The mechanistic studies show that this compound can increase the accumulation of anticancer drugs in both ABCG2- and ABCB1-overexpressing cancer cell lines, resulting from the blocked efflux function of the MDR cancer cell lines. This inhibition is due to the barred ABCG2 and ABCB1 ATPase activities rather than altering the expression or localization of ABCG2 or ABCB1 transporters. The previous studies showed that non-basic chalcones were ABCG2-specific inhibitors; however, we found that non-basic chalcone CYB-2 can be developed as an ABCG2/ABCB1 dual inhibitor to overcome MDR in cancers that co-express both ABCG2 and ABCB1. Moreover, non-basic chalcone CYB-2 has synthetic tractability compared to other chalcone-based derivatives.

Ultrafast broadband nonlinear optical properties and excited-state dynamics of two bis-chalcone derivatives.

The development of organic nonlinear optical (NLO) chromophores is vital for various fields such as two-photon biomedical imaging, optical limiting, etc. In this work, two bis-chalcone molecules 1,4-bis[3-(2,4-dimethoxyphenyl)-2-acryloyl]benzene (C1) and 4,4′-bis[3-(2,4-bimethoxy phenyl)-2-acryloyl]biphenyl (C2) were synthesized and characterized. The excited-state dynamics of these two chromophores were studied using femtosecond transient absorption (TA) measurements. And their broadband nonlinear absorption properties and optical limiting (OL) response were investigated by femtosecond open-aperture Z-scan and intensity-dependent transmittance measurements in the wavelength range from 515 nm to 800 nm, respectively. The TA results demonstrate that C2 has strong excited-state absorption behavior and longer lifetime. In addition, the nonlinear absorption response of C2 was found to be superior to that of C1 in the visible range after 500 nm, which is attributed to a two-photon-absorption induced excited-state absorption mechanism. These results indicate that the nonlinear optical response and excited-state dynamics in bis-chalcone compounds could be enhanced via intramolecular charge-transfer.

Investigation of ultrafast optical nonlinearities in novel bis-chalcone derivatives

In order to further exploit the optical nonlinearities in chalcone derivatives, two bis-chalcone molecules (C1 &C2) are synthesized. The third-order optical nonlinearities of both molecules are investigated via Z-scan. Enhanced nonlinear absorption and refraction are measured in C1 due to its superior planar π-conjugation over C2. Furthermore, an ultrafast sign change in both nonlinear absorption and refraction are revealed in C1 under femtoseconds and picoseconds lasers. A sub-picosecond ultrafast transfer is illustrated via femtoseconds transient absorption spectrum and considered as the mechanism behind the sign change. The results of this research may further extend the potential of chalcone derivatives in nonlinear optical applications and provide another method to tune the optical nonlinearity in such materials.

Synthesis, biological evaluation and molecular docking studies of bis-chalcone derivatives as xanthine oxidase inhibitors and anticancer agents

In this study, a series of B-ring fluoro substituted bis-chalcone derivatives were synthesized by Claisen-Schmidt condensation reactions and evaluated for their ability to inhibit xanthine oxidase (XO) and growth inhibitory activity against MCF-7 and Caco-2 human cancer cell lines, in vitro. According to the results obtained, the bis-chalcone with fluoro group at the 2 (4b) or 2,5-position (4g) of B-ring were found to be potent inhibitors of the enzyme with IC50 values in the low micromolar range. The effects of these compounds were about 7 fold higher than allopurinol. The binding modes of the bis-chalcone derivatives in the active site of xanthine oxidase were explained using molecular docking calculations. Also, compound 4g and 4h showed in vitro growth inhibitory activity against a panel of two human cancer cell lines 1.9 and 6.8 μM of IC50 values, respectively.

Density Functional Theory and Single Crystal X-ray Studies on Some Bis-Chalcone Derivatives

The three bis-chalcone compounds, (2E,6E)-2,6-bis(3-chlorobenzylidene)cyclohexanone (1), (2E,6E)-2,6-bis(2,3-dichlorobenzylidene)cyclohexanone (2) and (2E,5E)-2,5-bis(2,6-dichloro benzylidene) cyclopentanone (3), were studied with theoretical and single-crystal X-ray diffraction (XRD) methods. The molecular geometric parameters, frontier molecular orbitals, MEP, normal mode frequencies and the corresponding vibrational assignments, gauge-including atomic orbital (GIAO) 1H-NMR, 13C-NMR chemical shift values of the bis-chalcone compounds in the ground state have been calculated using the density functional (B3LYP) methods with 6-311G (d,p) basis set. These molecules demonstrate apparently a long and flat shape. Each molecule adopt an (E) configuration about the central olefinic bonds. The most important feature is stacking mode in the molecules. The calculated results reveal that the optimized geometries can well reproduce the crystal structure. The theoretical vibrational frequencies and 1H-NMR and 13C-NMR chemical shift values show good agreement with the experimental data.

Ultrasound-assisted synthesis of novel chalcone, heterochalcone and bis-chalcone derivatives and the evaluation of their antioxidant properties and as acetylcholinesterase inhibitors

The chalcone and bis-chalcone derivatives have been synthesized under sonication conditions via Claisen-Schmidt condensation with KOH in ethanol at room temperature (20–89%). The structures were established on the basis of NMR, IR, Single-crystal XRD, and MS. The best compound 3u had inhibitory activity (IC50 = 7.50 µM). The synthesis, the antioxidative properties, chemical reactivity descriptors supported in Density Functional Theory (DFT), acetylcholinesterase (AChE) inhibition and their potential binding modes, and affinity were predicted by molecular docking of a number of morpholine-chalcones and quinoline-chalcone. A series of bis-chalcones are also reported. Molecular docking and an enzyme kinetic study on compound 3u suggested that it simultaneously binds to the catalytic active site (CAS) and peripheral anionic site (PAS) of AChE. Moreover, the pharmacokinetic profile of these compounds was investigated using a computational method.

Synthesis and Biological Evaluation of Some Novel Claisen Products of 5‐Oxo‐1‐phenylpyrrolidine‐3‐carboxylic Acid as Antimicrobial and Antioxidant Agents

AbstractThe present communication deals with synthesis of some new bischalcone derivatives of 5‐oxo‐1‐phenylpyrrolidine‐3‐carboxylic acid by the base‐catalyzed Claisen‐Schmidt reaction. The antioxidant activity was evaluated by using the PFRAP assay systems and antimicrobial activity was studied against two gram positive [Bacillus pumilus (Bp) MTCC 1607, Staphylococcus aureus (Sa) MTCC 96], four Gram negative [Pseudomonas aeruginosa (Pa) MTCC 424, Salmonella typhi (St) MTCC 537, Klebsiella pneumoniae (Kp) MTCC 424, Escherichia coli (Ec) MTCC 64] bacteria and fungi [Candida albicans (Ca) MTCC 3017 and Candida tropicalis (Ct) MTCC 184] using Disc‐diffusion method. The antioxidant activity results were good and as far as antimicrobial activity was concerned some of the derivatives exhibited significant zone of inhibition on bacterial and fungal growth as compared to standard drugs.

Conventional and microwave-irradiated synthesis of new bischalcone derivatives

A series of 12 novel methyl- and halogen-substituted bischalcones containing an azo linkage was synthesized by a Claisen–Schmidt condensation between ( E)-1-{4-[(4-acetyl-2-hydroxyphenyl)diazenyl]phenyl}ethanone and various araldehydes using microwave irradiation and conventional procedures and the results were compared.