Recent advances in synthesis of stilbene derivatives via cross-coupling reaction.

The stilbenes are undoubtedly some of the most significant moieties in various bioactive natural and synthetic structures, and they are considered privileged structures. In recent years, the preparation of these structures via cross-coupling reactions has attracted much attention. In the current review, we present a summary of the recent developments in the construction of stilbene and stilbene derivatives by carbon-carbon coupling reactions of organic compounds in the presence of transition metal catalysts or under metal-free conditions. In this context, we outline the features of the important reactions, some product yields, and challenging reaction mechanisms.

Ugi Bis-Amide Derivatives as Tyrosinase Inhibitor; Synthesis, Biology Assessment, and in Silico Analysis.

Herein, a straightforward synthetic strategy mediated by Ugi reaction was developed to synthesize novel series of compounds as tyrosinase inhibitors. The structures of all compounds were confirmed by FT-IR, 1 H-NMR, 13 C-NMR, and CHNOS techniques. The tyrosinase inhibitory activities of all synthesized derivatives 5a-m were determined against mushroom tyrosinase and it was found that derivative 5c possesses the best inhibition with an IC50 value of 69.53±0.042 µM compared to the rest of the synthesized derivatives. Structure-activity relationships (SARs) showed that the presence of 4-MeO or 4-NO2 at the R2 position plays a key role in tyrosinase inhibitory activities. The enzyme kinetics studies showed that compound 5c is an noncompetitive inhibitor. For in silico study, the allosteric site detection was first applied to find the appropriate binding site and then molecular docking and molecular dynamic studies were performed to reveal the position and interactions of 5c as the most potent inhibitor within the tyrosinase active site. The results showed that 5c bind well with the proposed binding site and formed a stable complex with the target protein.

Vinyl azides in organic synthesis: an overview.

Among organic azides, vinyl azides have attracted significant attention, because of their unique properties in organic synthesis, which led to reports of many types of research on this versatile conjugated azide in recent years. This magical precursor can also be converted into intermediates such as iminyl radicals, 2H-azirines, iminyl metal complexes, nitrilium ions, and iminyl ions, making this compound useful in heterocycle synthesis.

Oxime Esters: Flexible Building Blocks for Heterocycle Formation.

Oxime esters as the applicable building blocks, internal oxidizing agents, and directing groups in the synthesis of -, S-, and O-containing heterocycle scaffolds have gained great attention in the last decade. This review provides an overview of recent advances in the cyclization of oxime esters with various functional group reagents under transition metal and transition metal-free catalyzed conditions. Moreover, the mechanistic aspects of these protocols are explained in detail.

Palladium supported magnetic Fucus Vesiculosus extract as a natural and novel catalyst for the synthesis of N-alkyl-2-(4-methyl-1-oxoisoquinolin-2(1H)-yl)-2-phenylacetamide derivatives.

In this paper, a novel catalyst is introduced based on the immobilization of palladium onto magnetic Fucus Vesiculosus extract (Pd@mFuVe catalyst). For the synthesis of Pd@mFuVe catalyst, Fucus Vesiculosus extract is obtained from the plant source, followed by the synthesis of superparamagnetic iron oxide nanoparticles (SPION) onto the extract. The catalyst is characterized by several methods, including scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDS), FT-IR spectroscopy, vibrating sample magnetometer (VSM), powder X-ray diffraction analysis (XRD), and inductively coupled plasma (ICP). The activity of Pd@mFuVe catalyst is studied in the synthesis of N-alkyl-2-(4-methyl-1-oxoisoquinolin-2(1H)-yl)-2-phenylacetamides. The products were synthesized in three steps, the synthesis of 2-iodobenzoic acid from 2-aminobenzoic acid, which participated in a multicomponent reaction with allylamine, aldehydes, and isocyanides, followed by a cyclization reaction, catalyzed by Pd@mFuVe catalyst. The product yields are high and the catalyst showed good reusability after 5 sequential runs. The most significant, Pd@mFuVe catalyst is fabricated from a plant extract source as a green support for the catalyst.

Design, synthesis, in vitro, and in silico evaluations of benzo[d]imidazole-amide-1,2,3-triazole-N-arylacetamide hybrids as new antidiabetic agents targeting α-glucosidase.

α-Glucosidase as a carbohydrate-hydrolase enzyme is a crucial therapeutic target for type 2 diabetes. In this work, benzo[d]imidazole-amide containing 1,2,3-triazole-N-arylacetamide derivatives 8a-n were synthesized and evaluated for their inhibitory activity against α-glucosidase. In vitro α-glucosidase inhibition assay demonstrated that more than half of the title compounds with IC50 values in the range of 49.0-668.5 µM were more potent than standard inhibitor acarbose (IC50 = 750.0 µM). The most promising inhibitor was N-2-methylphenylacetamid derivative 8c. Kinetic study revealed that compound 8c (Ki = 40.0 µM) is a competitive inhibitor against α-glucosidase. Significantly, molecular docking and molecular dynamics studies on the most potent compound showed that this compound with a proper binding energy interacted with important amino acids of the α-glucosidase active site. Study on cytotoxicity of the most potent compounds 8c, 8e, and 8g demonstrated that these compounds did not show cytotoxic activity against the cancer and normal cell lines MCF-7 and HDF, respectively. Furthermore, the ADMET study predicted that compound 8c is likely to be orally active and non-cytotoxic.