Design and synthesis of spirooxindole–pyrrolidines embedded with indole and pyridine heterocycles by multicomponent reaction: anticancer and in silico studies

Owing to the downsides of existing anticancer drugs, it is necessary to find more effective and selective anticancer agents for researchers in medicinal chemistry worldwide. Spirooxindoles are poised as privileged scaffolds because they exist in many natural products and bioactive molecules. Herein, we report an efficient, environment-friendly route for synthesizing a series of spirooxindoles using the 1,3-dipolar cycloaddition reaction of a dipolarophile with in situ generated azomethine ylide using ethanol as a solvent without any catalyst. The reaction offers potent biologically active spirooxindole fused with indole and pyridine heterocycles in good to excellent yield (69-94%) with higher diastereoselectivity. These synthesized compounds (4a-x) were screened for anticancer activity using A549, HepG-2, and SKOV-3 cancer cell lines using the MTT assay. Among all the screened compounds, 4u and 4w displayed substantial cytotoxic activity against HepG-2 cells at less than 10 μg mL−1. Molecular docking studies with the Bcl-2 and ALK receptor revealed that the higher binding energy was observed for 4u and 4w, and 4c and 4o with a value of −6.56 and −8.41, −6.73, and −7.14 kcal mol−1, respectively. Considering all the data, compounds 4u and 4w, 4c and 4o possess potent anticancer activity against respective receptors and can be the promising lead compounds for cancer drug discovery. © 2022 The Royal Society of Chemistr

2-(5-Bromothiophen-2-yl)-1-phenyl-1H-phenanthro[9,10-d]imidazole

In the title molecule, C25H15BrN2S, the phenanthrene system is slightly skewed, with a dihedral angle of 8.94 (16)° between the outer benzene rings. The imidazole ring makes dihedral angles of 15.18 (16), 2.94 (15) and 88.46 (16)°, respectively, with the thiophene ring, the central benzene ring of the phenanthrene unit and the phenyl ring attached to the latter unit. In the molecule, there are two C—H...π interactions present involving the phenyl ring. In the crystal, molecules are linked by C—H...N and C—H...Br hydrogen bonds, forming zigzag chains along the a axis. The chains are linked by C—H...π interactions, forming a three-dimensional supramolecular structure

A simple D–π–A system of phenanthroimidazole-π-fluorenone for highly efficient non-doped bipolar AIE luminogens: synthesis, and molecular optical, thermal and electrochemical properties

A series of hybrid organic bipolar fluorescent aggregation-induced emission (AIE) luminogens have been synthesized with D-π-A architecture using phenanthroimidazole as a conjugate by incorporating a fluorenone moiety at the C2 position of a rigid skeleton of 1,2-diphenyl-1H-phenanthro[9,10-d]imidazole. The synthesis was achieved by the Suzuki coupling reaction between 2-(4-bromophenyl)-1-phenyl-1H-phenanthro[9,10-d]imidazole and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-9-one. All derivatives of the product were found to be thermally stable, with high melting and high decomposition temperatures. The phenanthroimidazoles P1-P5 displayed the natural properties of AIE. Wide colour contrast between the green and yellow regions was demonstrated by these luminogens. Among them, P1 displayed higher quantum yield and long lifetime properties. Thus, the obtained results clearly demonstrate that all the luminogens are promising materials for research and use in optoelectronic devices, sensing applications, biological probes and intercellular imaging

Ru(II)-Catalyzed Regiospecific C–H/O–H Oxidative Annulation to Access Isochromeno[8,1-<i>ab</i>]phenazines: Far-Red Fluorescence and Live Cancer Cell Imaging

A facile ruthenium­(II)-catalyzed regiospecific C–H/O–H oxidative annulation methodology was developed to construct isochromeno­[8,1-<i>ab</i>]­phenazines. This methodology delivers various advantages, such as scope for diverse substrates, tolerance to a range of functional groups, stability under air, and yields regioselective products. This methodology was successfully applied to synthesize far red (FR) fluorescent probes for live cancer cell imaging. The synthesized compounds displayed notable fluorescence properties in solution and thin-film. Their application in live cancer cell imaging was investigated using various cancer cell lines. The synthesized compound showed prominent FR fluorescence, with high quantum yield, and exhibited better cell-imaging properties, with excellent biocompatibility

Ru(II)-Catalyzed Regiospecific C–H/O–H Oxidative Annulation to Access Isochromeno[8,1-<i>ab</i>]phenazines: Far-Red Fluorescence and Live Cancer Cell Imaging

A facile ruthenium­(II)-catalyzed regiospecific C–H/O–H oxidative annulation methodology was developed to construct isochromeno­[8,1-<i>ab</i>]­phenazines. This methodology delivers various advantages, such as scope for diverse substrates, tolerance to a range of functional groups, stability under air, and yields regioselective products. This methodology was successfully applied to synthesize far red (FR) fluorescent probes for live cancer cell imaging. The synthesized compounds displayed notable fluorescence properties in solution and thin-film. Their application in live cancer cell imaging was investigated using various cancer cell lines. The synthesized compound showed prominent FR fluorescence, with high quantum yield, and exhibited better cell-imaging properties, with excellent biocompatibility