2,4-Thiazolidinedione (CAS 2295-31-0) | Core Scaffold for Antidiabetic Agents
Product Concept
2,4-Thiazolidinedione (CAS 2295-31-0), a heterocyclic organic compound with the molecular formula C₃H₃NO₂S, serves as the fundamental pharmacophore for thiazolidinedione-class antidiabetic drugs. This unique bicyclic structure combines ketone and thiazole functionalities, enabling potent peroxisome proliferator-activated receptor gamma (PPARγ) agonist activity. With a molecular weight of 117.13 g/mol and melting point of 165-167°C, this pale yellow crystalline powder demonstrates optimal solubility in polar aprotic solvents (DMSO >100 mg/mL) while maintaining stability under nitrogen atmosphere. Its electronic configuration allows for both hydrogen bonding and π-π stacking interactions, making it indispensable in medicinal chemistry and drug discovery.
Technical Specifications
- Molecular Formula: C₃H₃NO₂S
- Molecular Weight: 117.13 g/mol
- Appearance: Pale yellow crystalline powder
- Purity: ≥98% (HPLC)
- Melting Point: 165-167°C
- Solubility: DMSO (120 mg/mL), Ethanol (15 mg/mL)
- Storage: 2-8°C under inert gas
Mechanistic Action
- PPARγ Activation: Binds to nuclear receptor with EC₅₀ = 0.3-0.8 μM
- Insulin Sensitization: Enhances glucose uptake in adipocytes
- Gene Regulation: Modulates adiponectin expression
- ROS Scavenging: Exhibits antioxidant activity via thioredoxin system
Multidisciplinary Applications
Pharmaceutical Development
- Rosiglitazone/Pioglitazone precursor
- Type 2 diabetes drug discovery
- Nonalcoholic steatohepatitis (NASH) therapy
- Anticancer agent development
Organic Synthesis
- Building block for heterocyclic compounds
- Ligand in transition metal catalysis
- Intermediate for fluorescent probes
Biochemical Research
- PPARγ pathway studies
- Adipocyte differentiation analysis
- Insulin resistance modeling
Synthetic Pathways
- Condensation of thiourea with diethyl oxalacetate
- Cyclization using phosphorus oxychloride
- Microwave-assisted synthesis from cysteamine
- Catalytic asymmetric synthesis
Quality Assurance
- HPLC-PDA purity analysis (C18 column)
- ¹H/¹³C NMR structural confirmation
- Elemental analysis (C, H, N, S)
- Residual solvent testing per ICH Q3C
- Karl Fischer moisture analysis (<0.5%)
Safety & Compliance
- Acute Toxicity (LD₅₀): 550 mg/kg (oral, rat)
- GHS Classification: Acute Toxicity Category 4
- Proper PPE: Nitrile gloves, lab coat, eye protection
- Disposal: Incineration with alkaline scrubber