The synthesis of (E)-1-(1-benzyl-5-methyl-1H-1,2,3-triazol-4-yl)-3-phenyl-2-propen-1-one derivatives was carried out in two steps, using benzylic chloride derivatives as starting material. The structural determination of intermediates and final products was performed by spectroscopic methods: infrared spectroscopy, nuclear magnetic resonance spectroscopy and mass spectrometry (IR, NMR, and MS). In vitro evaluation of cytotoxic activity on adherent and non-adherent cells showed that triazole chalcones exhibited significant activity against three of the five cell lines studied: non-Hodgkin lymphoma U937, glioblastoma multiform tumor T98G, and gallbladder cancer cells Gb-d1. In contrast, the cytotoxic activity observed for cervical cancer HeLa and gallbladder adenocarcinoma G-415 was considerably lower. Additionally, in the cell lines where activity was observed, some compounds demonstrated an In vitro inhibitory effect superior to that of the control, paclitaxel. Molecular docking studies revealed specific interactions between the synthesized ligands and therapeutic targets in various cell lines. In U937 cells, compounds 4a and 4c exhibited significant inhibition of vascular endothelial growth factor receptor (VEGFR) kinase, correlating with their biological activity. This effect was attributed to favorable interactions with key residues in the binding site. In T98G cells, compounds 4r and 4w showed affinity for transglutaminase 2 (TG2) protein, driven by their ability to form hydrophobic interactions. In Gb-d1 cells, compounds 4l and 4p exhibited favorable interactions with mitogen-activated protein kinase (MEK) protein, similar to those observed with the known inhibitor selumetinib. In HeLa cells, compounds 4h and 4g showed activity against dihydrofolate reductase (DHFR) protein, driven by hydrogen bonding interactions and favorable aromatic ring orientations. On the other hand, compounds 4b and 4t exhibited no activity, likely due to unfavorable interactions related to halogen substitutions in the aromatic rings.
This article describes the development of a nickel-catalyzed regio- and diastereoselective formal [3+2] cycloaddition between N-substituted indoles and donor–acceptor cyclopropanes to synthesize cyclopenta[b]indoles. Optimized reaction conditions provide the desired nitrogen-containing cycloadducts in up to 93% yield and dr 8.6:1 with complete regioselectivity. The substrate scope showed high tolerance to various substituted indoles and cyclopropanes, resulting in the synthesis of six new cyclopenta[b]indoles and the isolation of five derivatives previously reported in the literature. In addition, a mechanistic proposal for the reaction was studied through online reaction monitoring by ESI-MS, allowing for the identification of the reactive intermediates in the Ni(II) catalyzed process. X-ray crystallography confirmed the structure and relative endo stereochemistry of the products. This method enables the fast and efficient construction of fused indolines from readily accessible starting materials.
Developing sustainable paradigms for nanomaterial synthesis is essential to reduce the environmental impact of conventional chemical routes. Herein, we report a green, phytochemically mediated synthesis of MnFe2O4NPs using aqueous grapefruit (Citrus paradisi) peel extracts. The bioflavonoid and polyphenolic constituents functioned as dual-functional biogenic reducing and stabilizing agents. FTIR analysis verified spinel lattice metal–oxygen bonds and surface-bound biogenic groups, while SEM imaging revealed the surface morphology and structural aggregation of the nanoparticles. Once integrated into an electroanalytical platform (MnFe2O4NPs/GCE), the modified interface exhibited robust electrocatalytic activity toward sulfite oxidation in an acetate buffer (pH = 4.0). Mixed-valence dynamics (Mn2+/Mn3+ and Fe2+/Fe3+) significantly amplified anodic currents and lowered the kinetic overpotential. Under optimized chronoamperometric conditions, the sensor demonstrated a wide linear range (1–100 μM, r = 0.999), a low detection limit (LOD = 0.045 μM), a limit of quantification (LOQ = 0.136 μM) and excellent selectivity against co-existing ionic and organic interferents. This study provides a simple, eco-friendly, and technically robust strategy for fabricating high-performance electrochemical platforms for food and environmental monitoring.