The Michael addition reaction of barbituric acid with chalcones incorporating the indole scaffold was achieved by using a highly efficient bimetallic Iron-palladium catalyst in the presence of acetylacetone (acac). This catalytic approach produced the desired products in a simple operation and low catalyst loading with acceptable yield of the new hybrids. All tested compounds were subjected for biological activity on αglucosidase and α-amylase. The results revealed that all synthesized compounds exhibited very good activity against both enzymes when compared to positive control (acarbose). Moreover, compound 5o showed the best activity whereas its IC 50 (μM) are 13.02 + 0.01 and 21.71 + 0.82 for α-glucosidase and α-amylase respectively. Both compounds 5o and 5l exhibited high similarity in binding mode and pose with amylase protein (4UAC). The obtained data may be used for developing potential hypoglycemic agents.[a] Prof.

A sensitive colorimetric L-chemosensor 1,3-dimethyl-5-(thien-2-ylmethylene)-pyrimidine-2,4,6-(1[Formula: see text]-trione was developed by Knoevenagel combination of barbituric acid with thiophene aldehyde chelating moiety. The sensor displayed a high colorimetric Cu(II)X2 response; a dramatic methanol color change was recorded depending on anion type ([Formula: see text], Cl[Formula: see text], ClO[Formula: see text], NO[Formula: see text], OAc[Formula: see text], and SO[Formula: see text]. Off-on-off decolorized halochromism of the L-chemosensor/CuBr2 was recorded in an acidic medium. The structure of the L-chemosensor was confirmed by single-crystal X-ray diffraction, elemental analysis, and molecular spectroscopic tools such as UV–Vis, Fourier transform infra-red, 1H, and [Formula: see text]C nuclear magnetic resonance (NMR) spectroscopy. The thermal stability of the L-chemosensor was experimentally evaluated by thermogravimetric analysis. The structural optimized parameters of the ligand matched the crystallographic data, and the intermolecular forces were computed by Hirshfeld surface analysis. Electronic absorption in several solvents and 1H NMR were correlated with the computed spectra in the gaseous state. The HOMO/LUMO, global reactivity descriptor quantum parameters, Mulliken charge population, and molecular electrostatic potential of the L-chemosensor were also computed.

An efficient and practical method for the synthesis of 2,6-diaryl-4-oxo-N,N′-di(pyridin-2-yl)cyclohexane-1,1-dicarboxamide is described in this present study, which occurs through a double Michael addition reaction between diamide and various dibenzalacetones. The reaction was carried out in dichloromethane (DCM) in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The anticancer activities of the synthesized compounds were evaluated in several cancer cell lines, including MCF-7, MDA-MB-231, SAS, PC-3, HCT-116, HuH-7 and HepG2 cells. From these experiments, we determined that MDA-MB-231 was the most sensitive cancer cell line to the compounds 3c, 3e, 3d, 3j and 3l, which exhibited variable anticancer activities (3l [IC50 = 5 ± 0.25 µM] > 3e [IC50 = 5 ± 0.5 µM] > 3c [IC50 = 7 ± 1.12 µM] > 3d [IC50 = 18 ± 0.87 µM] > 3j [IC50 = 45 ± 3 µM]). Of these, 3l (substituted p-trifluoromethylphenyl and chloropyridine) showed good potency (IC50 = 6 ± 0.78 µM) against HCT-116 colorectal cancer cells and exhibited high toxicity against HuH-7 liver cancer cells (IC50 = 4.5 ± 0.3 µM). These values were three times higher than the values reported for cisplatin (IC50 of 8 ± 0.76 and 14.7 ± 0.5 µM against HCT-116 and HuH-7 cells, respectively). The highest α-glucosidase inhibitory activity was detected for the 3d, 3i and 3j compounds. The details of the binding mode of the active compounds were clarified by molecular docking studies.

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The crystal structures of five new chalcones derived from N-ethyl-3-acetylindole with different substituents were investigated: (E)-3-(4-bromophenyl)-1-(1-ethyl-1H-indol-3-yl)prop-2-en-1-one (3a); (E)-3-(3-bromophenyl)-1-(1-ethyl-1H-indol-3-yl)prop-2-en-1-one (3b); (E)-1-(1-ethyl-1H-indol-3-yl)-3-(4-methoxyphenyl)prop-2-en-1-one (3c); (E)-1-(1-ethyl-1H-indol-3-yl)-3-mesitylprop-2-en-1-one (3d); and (E)-1-(1-ethyl-1H-indol-3-yl)-3-(furan-2-yl)prop-2-en-1-one (3e). The molecular packing of the studied compounds is controlled mainly by C–H⋅⋅⋅O hydrogen bonds, C–H⋅⋅⋅π interactions, and π···π stacking interactions, which were quantitatively analyzed using Hirshfeld topology analysis. Using density functional theory (DFT) calculations, the order of polarity (3b ˂ 3d ˂ 3e ˂ 3a ˂ 3c) was determined. Several chemical reactivity indices such as the ionization potential (I), electron affinity (A), chemical potential (μ), hardness (η), electrophilicity (ω) and nucleophilicity (N) indices were calculated, and these properties are discussed and compared. In addition, the antiproliferative activity of the five new chalcones was studied.

5-[(3-Fluorophenyl)(2-hydroxy-6-oxocyclohex-1-en-1-yl)-methyl]-6-hydroxy-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 3 was synthesized via a multicomponent reaction. The Aldol-Michael addition reactions of N,N-dimethylbarbituric acid, cyclohexane-1,3-dione, and 3-fluorobenzaldehyde in aqueous solution gave the product in high yield. The molecular structure of the compound was confirmed by spectroscopic methods and X-ray crystallography. The title compound (C 19 H 19 FN 2 O 5 •H 2 O) crystallizes in the Monoclinic form, P2 1 /c, a = 7.8630 (5) Å,