Coumarin-thiazole and -oxadiazole derivatives: Synthesis, bioactivity and docking studies for aldose/aldehyde reductase inhibitors

A novel, green and cost-effective heterogeneous nanocatalyst was synthesized by supporting copper (I) oxide nanoparticles on magnetic agar (Cu2O/Agar@Fe3O4). Then, it was characterized with multipl...

https://www.tandfonline.com/doi/pdf/10.1080/17518253.2019.1679263

Agar: a natural and environmentally-friendly support composed of copper oxide nanoparticles for the green synthesis of 1,2,3–triazoles

Ninhydrin (1,2,3-indanetrione hydrate) has a remarkable breadth in different fields, including organic chemistry, biochemistry, analytical chemistry and the forensic sciences. For the past several years, it has been considered an important building block in organic synthesis. Therefore, there is increasing interest in ninhydrin-based multicomponent reactions to rapidly build versatile scaffolds. Most of the works described here are simple reactions with readily available starting materials that result in complex molecular architectures. Some of the synthesized compounds exhibit interesting biological activities and constitute a new hope for anticancer agents. The present review aims to highlight the multicomponent reactions of ninhydrin towards diverse organic molecules during the period from 2014 to 2019.

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Recent applications of ninhydrin in multicomponent reactions

In a continuation of our previous work for the exploration of novel enzyme inhibitors, two new coumarin-thiazole 6(a-o) and coumarin-oxadiazole 11(a-h) hybrids have been designed and synthesized. All the compounds were characterized by 1H- and 13C-NMR spectroscopy and elemental analysis. New hybrid analogs were evaluated against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) in order to know their potential for the prevention of Alzheimer's disease (AD). In coumarinyl thiazole series, compound 6b was found as the most active member against AChE having IC50 value of 0.87 ± 0.09 μM, while the compound 6j revealed the same efficacy against BuChE with an IC50 value of 11.01 ± 3.37 μM. In case of coumarinyl oxadiazole series, 11a was turned out to be the lead candidate against AChE with an IC50 value of 6.07 ± 0.23 μM, whereas compound 11e was found significantly active against BuChE with an IC50 value of 0.15 ± 0.09 μM. To realize the binding interaction of these compounds with AChE and BuChE, the molecular docking studies were performed. Compounds from coumarinyl thiazole series with potent AChE activity (6b, 6h, 6i, and 6k) were found to interact with AChE in the active site with MOE score of -10.19, -9.97, -9.68, and -11.03 Kcal.mol-1, respectively. The major interactions include hydrogen bonding, π-π stacking with aromatic residues, and interaction through water bridging. The docking studies of coumarinyl oxadiazole derivatives 11(a-h) suggested that the compounds with high anti-butyrylcholinesterase activity (11e, 11a, and 11b) provided MOE score of -9.9, -7.4, and -8.2 Kcal.mol-1, respectively, with the active site of BuChE building π-π stacking with Trp82 and water bridged interaction.

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Combined in Vitro and in Silico Studies for the Anticholinesterase Activity and Pharmacokinetics of Coumarinyl Thiazoles and Oxadiazoles.

ZnO‐Nanorods as an Efficient Catalyst for the Synthesis of 1,3‐Thiazolidine Derivatives by Aqueous Multicomponent Reactions of Isothiocyanates

Efficient synthesis of functionalized 2,4-diaminothiazoles from tetramethylguanidine, isothiocyanates, and α-bromoketones

The Hantzsch method for thiazole synthesis is modified via the reaction of 2-chloro-1,3-dicarbonyl compounds with 2-(amidosulfanylenemethyl)-1,1,3,3-tetramethylguanidines (prepared in situ from tetramethylguanidine and isothiocyanates), to afford functionalized 2-imino-1,3-thiazoles in good yields.

A synthesis of functionalized 2-imino-1,3-thiazoles from tetramethylguanidine, isothiocyanates, and 2-chloro-1,3-dicarbonyl compounds

A copper-catalyzed multicomponent reaction between terminal alkynes, sulfonyl azides, and oximes for the synthesis of N-tosylacetoyloxy alkanimines is reported. This one-pot procedure is carried out in the presence of copper(I) iodide in acetonitrile at room temperature.

Alaleh Malekafzali

Papers

Efficient synthesis of functionalized 2,4-diaminothiazoles from tetramethylguanidine, isothiocyanates, and α-bromoketones

A synthesis of functionalized 2-imino-1,3-thiazoles from tetramethylguanidine, isothiocyanates, and 2-chloro-1,3-dicarbonyl compounds

Sulfonoketenimides as Key Intermediates for the Synthesis of N-Tosyl-acetoyloxy Alkanimines

Tandem synthesis of trichloromethylated [3.3.3]propellanes from trichloroacetamidines and a ninhydrin–malononitrile adduct

Formation of Highly Functionalized Thiophenes by Reaction of Tetramethylthiourea, Acetylenic Esters, and α-Haloketones