What Is Thiazolidine?
Thiazolidine is a heterocyclic compound with the chemical formula C3H7NS, identifiable by its CAS number 504-78-9. It is a clear, colorless liquid at room temperature, with a molecular weight of 89.16, a boiling point of 72~75℃, and a density of 1.131g/cm3. The flash point is 132.8°F (56°C). It’s crucial to handle Thiazolidine cautiously, as it produces hazardous decomposition products like carbon oxides, nitrogen oxides (NOx), and sulfur oxides when ignited. Stable under normal storage conditions, it should be kept away from heat, flame, sparks, and strong oxidizers.
Uses of Thiazolidine
While Thiazolidine itself is not commonly used, its derivatives are significant in pharmaceuticals, particularly in β-lactam antibiotics like penicillin and thiazolidinedione (TZD) diabetes drugs. Thiazolidinedione drugs, used in treating type 2 diabetes, improve insulin resistance by binding to PPAR-gamma, a nuclear receptor, and function as transcriptional regulators. These drugs are mainly effective in reducing insulin resistance in peripheral tissues.
Principle of Thiazolidine
Thiazolidine can be synthesized through the hydrolysis of phthalimidoethyl mercaptan or by the condensation reaction of thiols with aldehydes or ketones. This reaction is reversible, leading to the instability of many Thiazolidine derivatives, which easily hydrolyze in water to yield thiols and aldehydes or ketones.
Types of Thiazolidine
1. Thiazolidine as a Reagent
As a chemical reagent, Thiazolidine is sold mainly for research and development in various capacities and can be stored at room temperature.
2. Thiazolidine Diabetes Drugs
Thiazolidinedione derivatives, used as diabetes medications, have seen varied market availability. While Troglitazone was withdrawn due to liver damage concerns, Pioglitazone Hydrochloride and Rosiglitazone remain in use, albeit with some restrictions due to potential health risks.
3. Thiazolidine in β-Lactam Antibiotics
The thiazolidine ring is a crucial component in many β-lactam antibiotics, including penicillin. These antibiotics function by inhibiting bacterial cell wall synthesis, offering both bacteriostatic and bactericidal actions.