6335-34-8

Usage

Uses

Used in Pharmaceutical Industry:
(5Z)-5-(2-chlorobenzylidene)-3-[2-(morpholin-4-yl)-2-oxoethyl]-2-thioxo-1,3-thiazolidin-4-one is used as a potential pharmaceutical agent for its possible anti-inflammatory, anti-tumor, anti-microbial, and anti-tuberculosis properties. The specific substitution pattern on the thiazolidine ring may contribute to its bioactivity, making it a candidate for further research and development in the pharmaceutical field.
Used in Research and Development:
In the scientific community, (5Z)-5-(2-chlorobenzylidene)-3-[2-(morpholin-4-yl)-2-oxoethyl]-2-thioxo-1,3-thiazolidin-4-one serves as a subject for research and development to better understand its bioactive properties and potential applications. Further studies are needed to explore its therapeutic effects and to determine its safety and efficacy in various medical applications.

Upstream product

• 519-87-9 N,N-diphenylacetamide 
• 122-39-4 diphenylamine 
• 598-21-0 2-Bromoacetyl bromide 
• 22118-09-8 2-bromoacetyl chloride 

Downstream Products

• 3335-98-6 1-phenyl-1,3-dihydro-indol-2-one 
• 519-87-9 N,N-diphenylacetamide 
• 681121-99-3 (2R,3S)-3-Phenyl-oxirane-2-carboxylic acid diphenylamide 
• 32443-44-0 N,N-Diphenyl-2-(triphenyl-λ⁵-arsanylidene)-acetamide 

Relevant academic research and scientific papers

Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid-Photoredox Hybrid Catalyst for the Generation of α-Carbonyl Radicals

A readily accessible organic-inorganic hybrid catalyst is reported for the reductive fragmentation of α-halocarbonyl compounds. The robust hybrid catalyst is a self-stabilizing combination of ZnCl2 Lewis acid and acridine orange as the photoactive organic dye. Mechanistic specifics of this hybrid catalyst have been studied in detail using both photophysical and electrochemical experiments. A systematic study enabled the discovery of the appropriate Lewis acid for the effective LUMO stabilization of α-halocarbonyl compounds and thereby lowering of reduction potential within the range of a standard organic dye. This strategy resolves the issues like dehalogenative hydrogenation or homo-coupling of alkyl radicals by guiding the photoredox cycle through an oxidative quenching pathway. The cooperativity between the photoactive organic dye and the Lewis acid counterparts empowers functionalization with a wide range of coupling partners through efficient and controlled generation of alkyl radicals and serves as an appropriate alternative to the expensive late transition metal-based photocatalysts. To demonstrate the application potential of this cooperative catalytic system, four different synthetic transformations of α-carbonyl bromides were explored with broad substrate scopes.

Design, synthesis, in vitro antiproliferative evaluation and in silico studies of new VEGFR-2 inhibitors based on 4-piperazinylquinolin-2(1H)-one scaffold

Angiogenesis is essential in the growth of solid tumors which need oxygen and nutrients supply to grow in size. The VEGF/VEGFR-2 signaling pathway plays an important role in tumor angiogenesis. Sorafenib is an FDA approved cancer therapeutic with activity

Visible-Light-Driven Aryl Migration and Cyclization of α-Azido Amides

This paper reports two new visible-light-promoted radical reactions of α-azido amides. By catalysis of [Ir(ppy)2(dtbbpy)]PF6 with i-Pr2NEt as the reducing agent, N-aryl α-azido tertiary amides were first converted to the corresponding aminyl radicals through reduction of the azido group; the aminyl radicals then underwent N-to-N aryl migration to give α-anilinyl-functionalized amides. α-Azido secondary amides, on the other hand, reacted with the solvent ethanol and i-Pr2NEt to afford the imidazolinone products.

γ-Substituted Allenic Amides in the Phosphine-Catalyzed Enantioselective Higher Order Cycloaddition with Azaheptafulvenes

Racemic γ-substituted allenes undergo enantioselective higher order [8 + 2]-cycloaddition with azaheptafulvenes using a chiral amino acid derived amidophosphine as catalyst, providing the corresponding azaazulenoid cycloadducts with excellent levels of regio-, diastereo-, and enantioselectivities. In this reaction, the activated allylic phosphonium ylide intermediate participates as the C2-component of the reaction, in contrast to the conventional reactivity of this type of zwitterionic intermediates as C3-components in cycloaddition reactions.

Synthesis of Oxindole Derivatives via Intramolecular C–H Insertion of Diazoamides Using Ru(II)-Pheox Catalyst

This work presented the efficient intramolecular aromatic C–H insertion of diazoacetamide. The 1a–1o diazo compounds (except for 1k) were converted into their corresponding oxindoles via an intramolecular C–H insertion reaction in the presence of a Ru catalyst. The Ru-Pheox catalyst was shown to be highly efficient in this transformation in terms of the regioselectivity, producing the desired products in excellent yield (99%). The efficiency of the Ru catalyst reached 580 (TON) and 156 min?1 (TOF).

Palladium(II) complexes of N, N-diphenylacetamide based thio/selenoethers and flower shaped Pd16S7 and prismatic Pd17Se15 nano-particles tailored as catalysts for C-C and C-O coupling

2-Bromo-N,N-diphenylacetamide (P1) prepared by reacting diphenylamine with α-bromoacetyl bromide, on treatment with Na2S and Na2Se generated in situ, has resulted in thio and selenoether ligands, L1 ((Ph2NCOCH2)2S) and L2 ((Ph2NCOCH2)2Se), respectively. Reacting these ligands with Na2PdCl4 in ethanol at room temperature resulted in their complexes [Pd(L1/L2)2Cl2] (C1/C2). P1, L1, L2, C1 and C2 were characterized by 1H, 13C{1H} and 77Se{1H} NMR spectroscopy, IR spectroscopy and High resolution mass spectrometry (HR-MS). Single crystal structures of all the five compounds were determined by X-ray diffraction. In both C1 and C2 the geometry of Pd is nearly square planar. Flower shaped Pd16S7 (size 26-50 nm) and prismatic Pd17Se15 NPs (size 20-55 nm) were synthesized by a single source precursor route (thermolysis at ～280 °C in trioctylphosphine) from air and moisture insensitive C1 and C2, respectively. These shapes of the two nanophases were unknown hitherto. They were characterized by powder X-ray diffraction (PXRD), SEM-EDX and HR-TEM and found to show good catalytic activity for Suzuki-Miyaura (Pd loading 0.5 mol%; yield up to 96%) and C-O (Pd loading 0.5 mol%; yield up to 96%) coupling reactions (at 100 °C) of aryl bromides with phenylboronic acid and phenol, respectively. The complexes C1 and C2 were found very efficient for Suzuki-Miyaura and C-O coupling as revealed by their optimum loading of 0.0001-0.01 and 0.1 mol% of Pd, respectively, for the two reactions. The reuse of the complexes or NPs as a catalyst is demonstrated.

New insights into the SAR and drug combination synergy of 2-(quinolin-4-yloxy)acetamides against Mycobacterium tuberculosis

2-(Quinolin-4-yloxy)acetamides have been described as potent and selective in vitro inhibitors of Mycobacterium tuberculosis (Mtb) growth. Herein, a new series of optimized compounds were found to demonstrate highly potent antitubercular activity, with minimum inhibitory concentration (MIC) values against drug-susceptible and drug-resistant Mycobacterium tuberculosis strains in the submicromolar range. Furthermore, the most active compounds had no apparent toxicity to mammalian cells, and they showed intracellular activities similar to those of isoniazid and rifampin in a macrophage model of Mtb infection. Use of the checkerboard method to investigate the association profiles of lead compounds with first- and second-line antituberculosis drugs showed that 2-(quinolin-4-yloxy)acetamides have a synergistic effect with rifampin. Ultimately, the good permeability, moderate rates of metabolism and low risk of drug-drug interactions displayed by some of the synthesized compounds indicate that 2-(quinolin-4-yloxy)acetamides may yield candidates to use in the development of novel alternative therapeutics for tuberculosis treatment.

Design, synthesis and evaluation of novel 19F magnetic resonance sensitive protein tyrosine phosphatase inhibitors

Fluorine is a highly attractive element for both medicinal chemistry and imaging technologies. To facilitate protein tyrosine phosphatase (PTP)-targeted drug discovery and imaging-guided PTP research on fluorine, several highly potent and 19F MR sensitive PTP inhibitors were discovered through a structure-based focused library strategy.

Synthesis of 1,4-Dicarbonyl Compounds from Silyl Enol Ethers and Bromocarbonyls, Catalyzed by an Organic Dye under Visible-Light Irradiation with Perfect Selectivity for the Halide Moiety over the Carbonyl Group

We report the visible-light-induced radical coupling reaction of silyl enol ethers with α-bromocarbonyl compounds to give 1,4-dicarbonyls. The reaction was effectively accelerated using an inexpensive organic dye (eosin Y) as a photoredox catalyst. 1,4-Dicarbonyl compounds alone were afforded, without the generation of carbonyl adducts of the α-halocarbonyls, which are usually generated in the presence of fluoride anions or Lewis acids. A variety of silyl enol ethers, α-bromoketones, α-bromoesters, and α-bromoamides were applied to this system to produce the coupling compounds.

Transition-Metal-Free Fluoroarylation of Diazoacetamides: A Complementary Approach to 3-Fluorooxindoles

An efficient transition-metal-free fluoroarylation reaction of N-aryl diazoacetamides with NFSI (N-fluorobenzenesulfonimide) is described. This reaction directly provides 3-fluorooxindole derivatives in yields of 67-93% with high selectivity via a carbene