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A new bischalcone comprising of hexyloxy (-OC6H2n+1) chain based on 'Donor (D)-π-Donor (D)' system was successfully designed and synthesized to demonstrate as emitting material for single-layer OLEDs. Density functional theory (DFT) assessment at B3LYP/6–31G(d,p) was computed to obtain frontier molecular orbitals (FMOs), chemical reactivity and molecular electrostatic potential (MEP). The utilization of alkoxy substructure towards the chalcone moiety has increased the solubility and contributed to HOMO–LUMO gap energy level 3.473 eV by UV–Vis spectroscopy and was found to have good agreement with the theoretical calculations. The investigations on their optical, electrochemical and thermal behaviour also were conducted via UV–Vis, cyclic voltammetry (CV), thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The entitled alkoxylated bischalcone (CSAB) revealed good thermal stability up to 300 °C and showed high glass transition temperatures. At positive potential, a quasi-reversible oxidation (Eox 1/2) peak at 2.40 V and negative potentials exhibited reduction peak at 0.78 V, respectively. The application of CSAB was tested in the form of thin film in respect to its conductivity in terms of electrical current and electroluminescence behaviour. It gave an intense yellow emission which has provided depth fundamental understanding on its potentiality featuring alkoxylated bischalcone moiety as solution-processed OLED material in optoelectronic interests. [ABSTRACT FROM AUTHOR]

This work reports the fabrication of blue luminescent bioplastic PLA films on doping with 4-chloro and 4-fluoro substituted bisarylidene cyclohexanone derivatives A and B. The successful doping of A and B to host matrix was evidenced by spectroscopic and analytical methods. The appearance of an absorption band at 1665 cm−1 owing to the conjugated alkene stretching frequency for bischalcones approved the presence of guest molecules. Similarly, the crystallinity of the films was improved by the addition of dopants above 2%. Molecular dynamics simulations of mechanical properties for neat PLA for lowest dopant concentration (2%) revealed decrease in Young's modulus and bulk modulus. The doping resulted in bathochromic shift from λmax 290 nm to the range of 335–340 nm with high degree of UV endurance. The PLA/dopant composite films (2–8%) effectively absorbed UVB as well as UVA radiation with promising SPF ranging from 12.71–39.2, 13.26–37.57 and UPF from 17.14–902.50, 9.39–197.01 for dopant A and B respectively. The photoluminescence emission maxima were observed in the blue region at 461 nm and 463 nm for the films doped with A and B. The effective scintillation with large Stoke's shift could be due to J-aggregate alignment of the dopants in the host matrix. The quantitative quantum yield (QY) was found to vary in the range of 0.17–0.42 for A and 0.15–0.46 for B which were comparable with flurophore anthracene with QY 0.27–0.36. Hence, these environmentally benign bioplastic composite materials with high SPF and UPF could find use as wide range UV filtering and also as blue emissive materials. [ABSTRACT FROM AUTHOR]

In the title bischalcone, C17H12Br2O, the olefinic double bonds are almost coplanar with their attached 4-bromophenyl rings [torsion angles = −10.2 (4) and −6.2 (4)°], while the carbonyl double bond is in an s-trans conformation with with respect to one of the C=C bonds and an s-cis conformation with respect to the other [C=C—C=O = 160.7 (3) and −15.2 (4)°, respectively]. The dihedral angle between the 4-bromophenyl rings is 51.56 (2)°. In the crystal, molecules are linked into a zigzag chain propagating along [001] by weak C—H...π interactions. The conformations of related bischalcones are surveyed and a Hirshfeld surface analysis is used to investigate and quantify the intermolecular contacts.

In the bischalcone molecule of the title compound, C24H18O4·2C3H7NO, the central benzene and terminal hydroxyphenyl rings form a dihedral angle of 14.28 (11)° and the central C=C double bond adopts a trans configuration. In the crystal, the bischalcone and solvate molecules are interconnected via O—H...O hydrogen bonds, which were investigated by Hirshfeld surface analysis. Solid-state fluorescence was measured at λex = 4400 Å. The emission wavelength appeared at 5510 Å, which corresponds to yellow light and the solid-state fluorescence quantum yield (Ff) is 0.18.

In the title compounds, (2E,2′E)-3,3′-(1,4-phenylene)bis[1-(2-methoxyphenyl)prop-2-en-1-one], C26H22O4 (I), (2E,2′E)-3,3′-(1,4-phenylene)bis[1-(3-methoxyphenyl)prop-2-en-1-one], C26H22O4 (II) and (2E,2′E)-3,3′-(1,4-phenylene)bis[1-(3,4-dimethoxyphenyl)prop-2-en-1-one], C28H26O6 (III), the asymmetric unit consists of a half-molecule, completed by crystallographic inversion symmetry. The dihedral angles between the central and terminal benzene rings are 56.98 (8), 7.74 (7) and 7.73 (7)° for (I), (II) and (III), respectively. In the crystal of (I), molecules are linked by pairs of C—H...π interactions into chains running parallel to [101]. The packing for (II) and (III), features inversion dimers linked by pairs of C—H...O hydrogen bonds, forming R22(16) and R22(14) ring motifs, respectively, as parts of [201] and [101] chains, respectively.

We report a new polymorph of (1E,4E)‐1,5‐bis(4‐fluorophenyl)penta‐1,4‐dien‐3‐one, C17H12F2O. Contrary to the precedent literature polymorph with Z′ = 3, our polymorph has one half molecule in the asymmetric unit disordered over two 50% occupancy sites. Each site corresponds to one conformation around the single bond vicinal to the carbonyl group (so‐called anti or syn). The other half of the bischalcone is generated by twofold rotation symmetry, giving rise to two half‐occupied and overlapping molecules presenting both anti and syn conformations in their open chain. Such a disorder allows for distinct patterns of intermolecular C—H...O contacts involving the carbonyl and anti‐oriented β‐C—H groups, which is reflected in three 13C NMR chemical shifts for the carbonyl C atom. Here, we have also assessed the cytotoxicity of three symmetric bischalcones through their in vitro antitumour potential against three cancer cell lines. Cytotoxicity assays revealed that this biological property increases as halogen electronegativity increases. [ABSTRACT FROM AUTHOR]

Herein, we report photoluminescence properties by embedding a purely organic fluorophore into a polymer matrix. Biopolymer-polylactic acid [PLA] doped with bischalcone, [1, 3-bis (4-bromobenzylidene) cyclohexan-2-one] is found to show exciting properties for applications in optoelectronics. This paper focuses on the preparation thin films with different dopant concentrations 2%, 4%, 6%, 8% (w/v) dispersed in PLA by solvent casting method. They are characterized by IR, SEM, TGA, DSC and Powder XRD; evidenced the formation matrix-dopant composite films. The UV absorbance of the pristine PLA film is observed at λ max 300 nm and for the doped films at λ max 330 nm. It is observed that as the dopant concentration increased, the intensity of absorbance also increased indicating the UV blocking property of the films with doped bischalcone. The prominent photoluminescence (PL) emission peak at 440 nm is obtained for doped PLA with dopant dependent increase in absolute quantum yield of 41–62%. Thus, the composite material obtained by doping the bischalcone into the polymer matrix is found to block UV radiations and emit light in the visible region, which could make these films versatile materials for optical applications. • Preparation of bischalcone doped PLA thin films by solvent casting method. • Characterization of the films by spectral and morphological studies. • UV abs and PL of the film show proportionate increase with the dopant concentration. • The material might find applications in optoelectronics. [ABSTRACT FROM AUTHOR]

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. [ABSTRACT FROM AUTHOR]

The inherent affinity of natural compounds for biological receptors has been comprehensively exploited with great success for the development of many drugs, including antimalarials. Here the natural flavoring compound vanillin has been used as an economical precursor for the synthesis of a series of novel bischalcones whose in vitro antiplasmodial activities have been evaluated against erythrocytic stages of Plasmodium falciparum. Bischalcones 9 , 11 and 13 showed promising antiplasmodial activity {Chloroquine ( CQ ) sensitive Pf 3D7 IC 50 (μM): 2.0, 1.5 and 2.5 respectively}but only 13 displayed potent activities also against CQ resistant Pf Dd2 and Pf Indo strains exhibiting resistance indices of 1.4 and 1.5 respectively. IC 90 (8 μM) of 13 showed killing activity against ring, trophozoite and schizont stages. Further, 13 initiated the cascade of reactions that culminates in programmed cell death of parasites including translocation of phosphatidylserine from inner to outer membrane leaflet, loss of mitochondrial membrane potential, activation of caspase like enzyme, DNA fragmentation and chromatin condensation. The combinations of 13 + Artemisinin (ART) exhibited strong synergy (ΣFIC 50 :0.46 to 0.58) while 13  +  CQ exhibited mild synergy ( ΣFIC 50 : 0.7 to 0.98) to mild antagonism ( ΣFIC 50 : 1.08 to 1.23) against Pf Indo. In contrast, both combinations showed marked antagonism against Pf 3D7 ( ΣFIC 50 : 1.33 to 3.34). These features of apoptosis and strong synergy with Artemisinin suggest that bischalcones possess promising antimalarial drug-like properties and may also act as a good partner drugs for artemisinin based combination therapies (ACTs) against Chloroquine resistant P. falciparum . [ABSTRACT FROM AUTHOR]

This review provides a comprehensive survey relating to the synthesis and biological applications of pyrazolines and related heterocycles in the last five years (2007–2011). These compounds are usually prepared from the cyclization of chalcones with hydrazine and its derivatives under the alcoholic conditions. The major incentive behind the synthesis of these compounds was the immense biological activities associated to these heterocyclic derivatives. The aim of this review is to find out different methods for the synthesis of pyrazoline derivatives.

In the title compounds, (2E,2'E)-3,3'-(1,4-phenylene)bis[1-(2-methoxyphenyl)-prop-2-en-1-one], C26H22O4 (I), (2E,2'E)-3,3'-(1,4-phenylene)bis[1-(3-methoxyphenyl) prop-2-en-1-one], C26H22O4 (II) and (2E,2'E)-3,30-(1,4-phenylene)bis[1-(3,4-dimethoxyphenyl)prop-2-en-1-one], C28H26O6 (III), the asymmetric unit consists of a half-molecule, completed by crystallographic inversion symmetry. The dihedral angles between the central and terminal benzene rings are 56.98 (8), 7.74 (7) and 7.73 (7)° for (I), (II) and (III), respectively. In the crystal of (I), molecules are linked by pairs of C--H···π interactions into chains running parallel to [101]. The packing for (II) and (III), features inversion dimers linked by pairs of C--H···O hydrogen bonds, forming R2²(16) and R2²(14) ring motifs, respectively, as parts of [201] and [101] chains, respectively. [ABSTRACT FROM AUTHOR]

In this paper, a new series of five-membered heterocyclic compounds containing pyrazoline and pyrimidine nucleus were synthesized under both conventional and ultrasonic irradiation conditions. In the first step, bischalcone derivatives were prepared by Claisen-Schmidt condensation of bisaldehydes and acetophenone in alkaline ethanol under conventional and ultrasonic conditions. In the second step, bispyrimidine and bispyrazolines were synthesized by the condensation reaction of bischalcones with thiourea/phenyl hydrazine in an alkaline medium. The ultrasound-assisted synthesis provides excellent yields in short reaction times at room temperature. The structures of the newly synthesized compounds were characterized by IR, H NMR, C NMR, mass and elemental analysis. The new synthesized bispyrimidine and bispyrazoline were used as new adsorbents for the excellent selective removal of silver and lead ions from aqueous mixed metal ion solution containing Cu(II), Co(II), Ni(II), and Zn(II) by batch technique. Also, the quantitative desorption was achieved for lead and silver ions with 0.5 M of HNO and HCl solutions, respectively. Graphical abstract: [ABSTRACT FROM AUTHOR]

This review provides a comprehensive survey relating to the synthesis and biological applications of pyrazolines and related heterocycles in the last five years (2007–2011). These compounds are usually prepared from the cyclization of chalcones with hydrazine and its derivatives under the alcoholic conditions. The major incentive behind the synthesis of these compounds was the immense biological activities associated to these heterocyclic derivatives. The aim of this review is to find out different methods for the synthesis of pyrazoline derivatives. [ABSTRACT FROM AUTHOR]

• A new bischalcone was synthesized and characterized by single crystal X-ray diffraction. • Intermolecular interactions are studied using Hirshfeld surface analysis. • In vitro and in silico antitumor evaluation was assessed against A549 cancer cell line. • Bischalcone compound has shown significant antitumor activity. • Good antibacterial and antifungal activity have shown by bischalcone. New bischalcone derivative 3-(2,6-dichlorophenyl)-1,5-diphenylpentane-1,5‑dione (C 23 H 18 Cl 2 O 2) 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 IC 50 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. [Display omitted] [ABSTRACT FROM AUTHOR]

Abstract: The cyclization of chalcone with N-4 substituted thiosemicarbazides under basic condition led to the formation of new compounds, thiocarbamoyl bis-pyrazoline derivatives. The structure of the compounds were elucidated by UV, IR, 1H NMR, 13C NMR and ESI-MS spectral data and thermogravimetric analysis, and their purities were confirmed by elemental analyses. The antiamoebic activity of these complexes was evaluated by microdilution method against HM1:IMSS strain of Entamoeba histolytica and the results were compared with the standard drug, metronidazole. Structure–activity relationship shows that the compound with aromatic substituents at the thiocarbamoyl group was more active than those with the cyclic groups. However, it was clear from the IC50 values that the compounds 15 and 20 are more active and both showed a structural resemblance having an electron withdrawing groups attached to the phenyl ring. MTT assay showed that all the compounds are non-toxic to human kidney epithelial cell line. [Copyright &y& Elsevier]

[Display omitted] • A series of bischalcone derivatives were synthesized by Claisen-Schmidt reaction. • In vitro cell culture cytotoxicity assays were performed on two different cancer cell lines. • Apoptotic status of cells was analyzed using flow cytometry. • Cell-cycle analysis was performed. • Molecular docking analysis was performed. 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 IC 50 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. [ABSTRACT FROM AUTHOR]

Bischalcone has gained much attention because of its wide range of application in pharmaceutical chemistry. This work aims to evaluate the antiproliferation effects and explore the anticancer mechanism of bischalcone analogs on human lung cancer A549 cells. In this study, we synthesized a series of bischalcone analogs via Aldol condensation reaction; MTT method was used to evaluate the antiproliferation effects; the 2′,7′-dichlorofluorescein fluorescence assay was used to determine the intracellular reactive oxygen species levels; the glutathione reductase-DTNB recycling assay was used to detect the redox imbalance; determination of thiobarbituric acid-reactive substance was used to evaluate the lipid peroxidation; Rhodamine 123 was used to test the mitochondrial membrane potential (MMP); the FITC/PI kit was used to detect the apoptosis; Western blotting was used to detect the expression of Bax and Caspase 3. After treatment with curcumin and bischalcone analogs, compounds 1d and 1g , the more stabilities compounds than curcumin, exhibited much higher potency in A549 cells than curcumin and other bischalcone analogs. Further mechanism of action studies revealed that 1d and 1g exhibited more stronger reactive oxygen species production abilities than curcumin and accompanied by the redox imbalance, lipid peroxidation, the loss of MMP, the activition of Bax and Caspase 3, and ultimately resulted in apoptosis of A549 cell. These data suggest that enhancing the reactive oxygen species generation ability of bischalcone analogs may be a promising strategy for the treatment of human lung cancer. This work demonstrates that bischalcone analogs showed more stability and more potent cytotoxicity than curcumin, and brought about A549 cell apoptosis by enhancing the reactive oxygen species production. Image 1 • Bischalcone analogs showed more stability and more potent cytotoxicity than curcumin. • " ortho effect " play a potent role in the cytotoxicity of bischalcone analogs. • Bischalcone analogs brought about human lung carcinoma cells apoptosis by improving reactive oxygen species generation. [ABSTRACT FROM AUTHOR]

Design and synthesis of a new type of bischalcones as an alternative to natural and synthetic bischalcones are reported for the first time. Key steps involved the solvent-free Claisen-Schmidt condensation of chalcones, and the successful first application of the diazotization-diazocoupling reaction in the synthesis of CNNC-linked bischalcones by simple structural modification of p-aminoacetophenone. The structures of all compounds were confirmed by means of FT-IR, (1) H and (13) C NMR, ESI/MS, and elemental analysis. In addition, the newly synthesized compounds were screened for carbonic anhydrase inhibition activities. Almost all bischalcones exhibited moderate-to-good inhibitory activities., (© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)