78374-71-7

Upstream product

• 3806-42-6 5-benzylidene-2-thioxothiazolidin-4-one 
• 100-46-9 benzylamine 
• 2295-31-0 thiazoline-2,4-dione 
• 100-52-7 benzaldehyde 
• 141-84-4 2-thioxo-4-thiazolidinone 
• 78374-90-0 N-benzyl-N'-3-phenylpropenoylthiourea 

Relevant academic research and scientific papers

γ-Aminobutyric acid hydrochloride supported on superparamagnetic γ-Fe2O3@SiO2 as a novel heterogeneous nanocatalyst for the synthesis of 2-amino-5-alkylidene-thiazol-4-one derivatives

γ-Aminobutyric acid hydrochloride immobilized on superparamagnetic γ-Fe2O3@SiO2 nanoparticles as a novel heterogeneous nanocatalyst was prepared for the first times. It was characterized by several techniques such as XRD, FT-IR, VSM, FE-SEM, EDS, and TGA analysis. The heterogeneous nanocatalyst was used for a convenient, mild, and one-pot efficient three-component preparation of 2-amino-5-alkylidene-thiazol-4-one derivatives under green conditions at room temperature. The main advantage of the method is easily recovery of the stable nanocatalyst by an external magnet from the reaction mixture.

Xanthine oxidase inhibitory properties and anti-inflammatory activity of 2-amino-5-alkylidene-thiazol-4-ones

Thirty 2-amino-5-alkylidene-thiazol-4-ones were assayed for inhibitory activity against commercial enzyme xanthine oxidase (XO) in vitro and XO in rat liver homogenate as well as for anti-inflammatory response on human peripheral blood mononuclear cells (PBMCs). 4-((2-Benzylamino-4-oxothiazol-5(4H)-ylidene)-methyl)benzonitrile showed the most potent inhibitory effect against commercial XO (IC50 = 17.16 μg/mL) as well as against rat liver XO (IC50 = 24.50 μg/mL). All compounds containing the 4-cyanobenzylidene group or (indol-3-yl)methylene group at the position 5 of thiazol-4-one moiety were moderately potent inhibitors of commercial XO. The assayed compounds were docked into the crystal structures of XO enzyme complexes with three diverse inhibitors (PDB codes: 1FIQ, 1VDV, and 1V97) using OEDocking software. Our results strongly point to a correlation between the data on inhibitory activity against commercial XO and data on antioxidant activity of studied compounds, screened using a lipid peroxidation (LP) method. 2-(Benzylamino)-5-((thiophen-2-yl)methylene)thiazol-4(5H)-one showed the highest anti-inflammatory response on PBMCs, exerted most probably through the NF-κB inhibition. Studied 2-amino-5-alkylidene-thiazol-4-ones obey the "Rule of five" and meet all criteria for good solubility and permeability.

Three-component one-pot synthetic route to 2-amino-5-alkylidene-thiazol-4-ones

A fast and straightforward three-component reaction to 2-amino-5-alkylidene-thiazol-4-ones is described. The one-pot methodology, reported for the first time, involves Knoevenagel condensation of aromatic aldehydes and rhodanine followed by displacement o

Traceless solid-phase synthesis of 2-amino-5-alkylidene-thiazol-4-ones

2-Amino-5-alkylidene-thiazol-4-ones bearing two diversity points are prepared by a solid-phase strategy exploiting rhodanine as the starting material. Rhodanine is first loaded on bromo-Wang resin, subjected to Knovenagel condensation with aldehydes, and cleaved off the resin in a traceless manner by means of an amine.

SYNTHESIS OF 2-SUBSTITUTED 5-ARYLIDENETHIAZOLIN-4-ONES FROM α,β-UNSATURATED ACYL ISOTHIOCYANATES

α,β-Unsaturated acyl isothiocyanates react with N-methylaniline to give thioureas which, when treated with bromine in chloroform, afford benzothiazoline derivatives.Under the same reaction conditions primary amines, diethylamine,piperidine and morpholine