Synthesis of Novel Triazole Incorporated Thiazolone Motifs Having Promising Antityrosinase Activity through Green Nanocatalyst CuI-Fe3O4@SiO2 (TMS-EDTA)

In the present work, novel 5-((1-benzyl-1,2,3-triazol-4-yl)methoxybenzylidene)-2-(arylamino)thiazol-4-one thiazolone incorporated triazole derivatives have been designed as tyrosinase inhibitors. The compounds were synthesized through click reaction in good yield. Moreover, the antityrosinas activity of the synthesized derivatives was evaluated. In the search for establishing a click copper-catalyzed azide/alkyne cycloaddition (CuAAC) reaction under strict conditions, in terms of a novel air-stable, a recyclable and efficient magnetic catalyst was planned for new triazole derivatives as a well-organized copper iodide supported on the functionalized Fe₃O₄@SiO₂ core-shell (CuI/Fe₃O₄@SiO₂(TMS-EDTA) nanoparticles). The engineered nanocatalyst synthesized for the first time and characterized by different methods, including FT-IR spectroscopy, XRD, FESEM, EDX, TEM, TGA, and BET analysis. The excellent catalytic performance in ethanol with high surface area (351.7 m²g⁻¹) and short reaction time for diverse functional groups (120–200 min), no use of toxic solvents, reusability of the catalyst, and using eco-friendly conditions are the advantageous of this work. Moreover,the nanocatalyst can be used at least five times without any significant decrease in the yield of the reaction. The thiazolidine-triazole derivatives 9a , 9c , 9e , and 9 g showed promising tyrosinase inhibitory activity with IC₅₀ values in the range of 5.90–9.81 μM. The compounds were found to be considerably more potent tyrosinase inhibitors than the reference inhibitor kojic acid (IC₅₀ = 18.36 μM).     

5-Oxo-hexahydroquinoline: an attractive scaffold with diverse biological activities

Molecular Diversity - 5-Oxo-hexahydroquinoline (5-oxo-HHQ) represents a biologically attractive fused heterocyclic core. Various synthetic analogs of 5-oxo-HHQ have been synthesized and assessed...     

2-Imino 2<Emphasis Type="Italic">H</Emphasis>-chromene and 2-(phenylimino) 2<Emphasis Type="Italic">H</Emphasis>-chromene 3-aryl carboxamide derivatives as novel cytotoxic agents: synthesis,biological assay,and molecular docking study

The inhibition of AKR₁B₁₀ has been recognized as a potential therapeutic approach to the treatment of various types of cancers. A novel series of compounds with imino-2H-chromen and phenylimino-2H-chromen scaffolds were synthesized by Knoevenagel condensation reaction. The in vitro cytotoxic activity of synthesized compounds was evaluated against MOLT-4 and SK-OV-3 cells. Among the tested compounds, N-(3,4-dimethoxyphenyl)-2-(phenylimino)-2H-chromene-3-carboxamide (8g) demonstrated potent inhibitory activity against both examined cell lines. The results of the molecular docking study suggested that this compound is involved in critical hydrogen-bonding interactions with the Val301 and Lue302 of AKR₁B₁₀ catalytic site.     

Synthesis and Cytotoxic Activity of Some Novel Dihyrobenzo[h]pyrano[3,2‐c]chromene Derivatives

Three‐component reaction of 4‐hydroxy‐2H‐benzo[h]chromen‐2‐one, aromatic aldehydes, and malononitrile in the presence of 1,4‐diazabicyclo[2.2.2]octane (DABCO) in ethanol at room temperature affords good yields of novel dihyrobenzo[h]pyrano[3,2‐c]chromene derivatives. The synthesized compounds examined by MTT assays for cytotoxic activity in two human cancer cell lines (MOLT‐4, HL‐60). Most of the evaluated compounds showed low inhibitory activity against tumor cell line at micromolar concentrations.     

5-Oxo-hexahydroquinoline and 5-oxo-tetrahydrocyclopentapyridine derivatives as promising antiproliferative agents with potential apoptosis-inducing capacity

Molecular Diversity - Discovery of novel anticancer agents is of crucial importance to expand the therapeutic options for cancer patients. In this study, a series of 49 5-oxo-hexahydroquinoline and...     

4H-benzochromene derivatives as novel tyrosinase inhibitors and radical scavengers: synthesis,biological evaluation,and molecular docking analysis

Molecular Diversity - A series of ethyl 2-amino-4H-benzo[h]chromene-3-carboxylate derivatives, having phenyl ring with diverse substituents at C4 position of 4H-benzochromene nucleus, were...     

Copper-catalyzed four-component synthesis of imidazo[1,2-a]pyridines via sequential reductive amination,condensation, and cyclization

A novel and efficient four-component approach for the synthesis of 2,3-disubstituted imidazo[1,2-a]pyridines is described. The copper-catalyzed reductive amination of 2-bromopyridine by sodium azide followed by sequential condensation and cyclization with aldehydes and isocyanides afforded the corresponding imidazo[1,2-a]pyridines in good yields.