20579-83-3

Usage

InChI:InChI=1/C9H7ClN2OS/c10-6-2-1-3-7(4-6)11-9-12-8(13)5-14-9/h1-4H,5H2,(H,11,12,13)

Upstream product

• 4947-89-1 1-(3-chlorophenyl)-2-thiourea 
• 105-39-5 chloroacetic acid ethyl ester 
• 108-42-9 3-chloro-aniline 
• 2564-05-8 2-chloro-N-(3-chlorophenyl)acetamide 

Downstream Products

• 299970-75-5 2-(3-chlorophenylimino)-5-benzylidene-4-thiazolidinone 
• 358399-18-5 2-(3-chlorophenylimino)-5-(2-chlorobenzylidene)-4-thiazolidinone 
• 358399-14-1 2-(3-chlorophenylimino)-5-(4-chlorobenzylidene)-4-thiazolidinone 
• 358399-41-4 2-(3-chlorophenylimino)-5-(4-hydroxybenzylidene)-4-thiazolidinone 
• 358399-28-7 2-(3-chlorophenylimino)-5-(3-nitrobenzylidene)-4-thiazolidinone 
• 358399-56-1 2-(3-chlorophenylimino)-5-(4-hydroxy-3-methoxybenzylidene)-4-thiazolidinone 

Relevant academic research and scientific papers

Novel 2-(substituted phenyl Imino)-5-benzylidene-4-thiazolidinones as possible non-ulcerogenic tri-action drug candidates: synthesis, characterization, biological evaluation And docking studies

The present research was aimed at the synthesis and screening of 35 novel 2-(substituted phenyl imino)-5-benzylidene-4-thiazolidinones having different substitutions at imino phenyl and arylidene groups. The title compounds were synthesized by Knoevenagel

Synthesis and biological evaluation of 2-phenylimino-5((5-phenylfuran-2-yl)methylene)thiazolidin-4-ones as IKK2 inhibitors

In a search for novel molecules to treat inflammatory disorders, we identified several compounds with inhibitory action against the IKK2 enzyme using in silico methods. Based on the virtual hit of compounds 1 and 2, a novel series of 2-phenylimino-5((5-phenylfuran-2-yl)methylene)thiazolidin-4-one derivatives was designed, synthesized, and evaluated for IKK2 inhibitory activity. Among the synthesized derivatives, compounds 17f and 19f showed good IKK2 inhibitory potency, which have 4-carboxaminophenyl on the 2-furan ring and a methoxy group on the phenylimino moiety at the 2-position of the core structure. The most potent compound was 2-(2,4-dimethoxyphenyl)imino-5((5(4-carboxaminophenyl)furan-2-yl)methylene)thiazolidin-4-one (19f, IC50 = 0.94 μM), which represents a synergic effect of the two virtual hit compounds against IKK2. We also identified compounds showing inhibitory activities against interleukin (IL)-17, CCK-8, and tumor necrosis factor-alpha (TNF-α), which are NF-κB-dependent pro-inflammatory cytokine mediators.

Effect of chloro and fluoro groups on the antimicrobial activity of 2,5-disubstituted 4-thiazolidinones: A comparative study

The article reports the synthesis of a series comprising of twenty-one 2,5-disubstituted-4-thiazolidinone derivatives, bearing 3-chloro-4-fluorophenyl imino, 4-chlorophenyl imino and 3-chlorophenyl imino groups at position-2 and substituted arylidene grou

Design, synthesis, cytoselective toxicity, structure-activity relationships, and pharmacophore of thiazolidinone derivatives targeting drug-resistant lung cancer cells

Ten cytoselective compounds have been identified from 372 thiazolidinone analogues by applying iterative library approaches. These compounds selectively killed both non-small cell lung cancer cell line H460 and its paclitaxel-resistant variant H460taxR at an IC50 between 0.21 and 2.93 μM while showing much less toxicity to normal human fibroblasts at concentrations up to 195 μM. Structure-activity relationship studies revealed that (1) the nitrogen atom on the 4-thiazolidinone ring (ring B in Figure 1) cannot be substituted, (2) several substitutions on ring A are tolerated at various positions, and (3) the substitution on ring C is restricted to the -NMe2 group at the 4-position. A pharmacophore derived from active molecules suggested that two hydrogen bond acceptors and three hydrophobic regions were common features. Activities against P-gp-overexpressing and paclitaxel-resistant cell line H460taxR and modeling using a previously validated P-gp substrate pharmacophore suggested that active compounds were not likely P-gp substrates.