5-(4-Methoxybenzylidene)-1,3-thiazolidine-2,4-dione

Base Information

• Chemical Name: 5-(4-Methoxybenzylidene)-1,3-thiazolidine-2,4-dione
• CAS No.: 6320-51-0
• Molecular Formula: C11H9NO3S
• Molecular Weight: 235.263
• NSC Number: 31205
• Nikkaji Number: J1.343.994J,J372.490E
• ChEMBL ID: CHEMBL85496
• Mol file: 6320-51-0.mol

Synonyms:5-(4-methoxybenzylidene)thiazolidine-2,4-dione;SKLB 010;SKLB-010;SKLB010

Chemical Property of 5-(4-Methoxybenzylidene)-1,3-thiazolidine-2,4-dione

Chemical Property:

• PSA: 80.70000
• Density: 1.391g/cm³
• LogP: 2.34790
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 235.03031432
• Heavy Atom Count: 16
• Complexity: 332

Purity/Quality:

97% ^*data from raw suppliers

NSC31205 >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C=C2C(=O)NC(=O)S2
• Isomeric SMILES: COC1=CC=C(C=C1)/C=C\2/C(=O)NC(=O)S2
• General Description: 2,4-Thiazolidinedione, 5-p-methoxybenzylidene-, also known as (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, is a novel glitazone compound with demonstrated hepatoprotective effects in Concanavalin A-induced acute liver injury in BALB/c mice. It exhibits potent inhibitory activity against chemotaxis of RAW264.7 cells stimulated by MCP-1 and significantly reduces serum levels of ALT and AST, indicating its efficacy in mitigating liver damage. 2,4-Thiazolidinedione, 5-p-methoxybenzylidene- is orally active, readily synthesized, and shows minimal toxicity in histopathological evaluations, making it a promising therapeutic candidate for acute liver injury.

Technology Process of 5-(4-Methoxybenzylidene)-1,3-thiazolidine-2,4-dione

There total 22 articles about 5-(4-Methoxybenzylidene)-1,3-thiazolidine-2,4-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

thiazoline-2,4-dione (2295-31-0) + 4-methoxy-benzaldehyde (123-11-5) → 5-(4-methoxybenzylidene)thiazolidine-2,4-dione (6320-51-0)

Guidance literature:

With piperidine; acetic acid; In toluene; at 80 ℃; Dean-Stark;

Reference yield: 97.0%

thiazoline-2,4-dione (2295-31-0) + 4-methoxy-benzaldehyde (123-11-5) → (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione (6320-51-0,74942-48-6,74942-63-5)

Guidance literature:

With acetic acid; In toluene; for 16h; Heating;

DOI:10.1016/S0040-4020(00)00361-6

Reference yield: 79.0%

thiazoline-2,4-dione (2295-31-0) + sodium hydroxy(4-methoxyphenyl)methanesulfonate (33402-67-4) → (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione (6320-51-0,74942-48-6,74942-63-5)

Guidance literature:

With trichlorophosphate; In toluene; for 8h; Solvent; Temperature; Reflux;

DOI:10.2174/15701786113106660081

upstream raw materials:

thiazoline-2,4-dione

4-methoxy-benzaldehyde

4-methoxybenzylidene thiosemicarbazone

chloroacetic acid

Downstream raw materials:

5-(4-Methoxybenzyliden)-3-hydroxymethylthiazolidinon-2,4

2-mercapto-3-(4-methoxyphenyl)-N-(N-methyl-N-phenylhydrazinocarbonyl)propenamide

3-hydrazino-6-(4-methoxybenzyl)-1,2,4-triazin-5(2H)-one

N-(hydrazinocarbonyl)-2-hydrazono-3-(4-methoxyphenyl)propanamide

Refernces

Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice

10.1021/jm901183d

The research focuses on the discovery of a novel glitazone, (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, as an orally active and readily available treatment for Concanavalin A-induced acute liver injury in BALB/c mice. The study involves the synthesis and screening of 53 small molecules from a small-molecule library, using a quick screening method to evaluate their potency in inhibiting chemotaxis of RAW264.7 cells stimulated by monocyte chemoattractant protein 1 (MCP-1). The most effective compounds were identified through in vitro inhibitory effects and further assessed in vivo for their hepatoprotective effects. The experiments utilized various reactants, including aromatic aldehydes, β-alanine, barbituric acid, thiobarbituric acid, and other chemical reagents, and employed techniques such as Knoevenagel reaction, Wittig reaction, and HPLC for compound synthesis and purity analysis. The biological activity was assessed through chemotaxis assays, serum aminotransferase level measurements, and histopathological evaluations. The study demonstrated that compound 4f significantly reduced serum levels of alanine aminotransaminase (ALT) and asparate aminotransaminase (AST) and showed hepatoprotective effects in the liver injury model, with minimal toxicity observed in histopathological assessments of major organs.