Thiazolines/Thiazolidines

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Introduction

Thiazolidines (C3H7NS) are heterocyclic organic compounds with a five-membered saturated ring containing a thioether group at the 1-position and an amine group at the 3-position. Thiazolidines are the colorless liquids of the sulfur analog of oxazolidines. Thiazolidine derivatives have aroused great interest among researchers due to their wide range of biological activities.

Thiazolines (C3H5NS), also known as dihydrothiazoles, are well known as 4,5-dihydro-1,3-thiazole or 4,5-dihydrothiazole. Thiazoline is a liquid with a pyridine-like odor which was first isolated from mouse urine in 1977. Normally, there are three isomers of thiazolines: 2-thiazoline, 3-thiazoline and 4-thiazoline.

Application

Thiazolidines have been applied as prodrug derivatives for various steroids containing a 3-carbonyl group to improve their topical anti-inflammatory activity. For example, thiazolidinones are saturated forms of thiazoles, which are thiazolidines bearing a carbonyl group. The 1,3-thiazolidin-4-ones possess wide range of pharmacological activities such as anti-cancer, anti-diabetic, anti-microbial, anti-viral, anti-inflammatory and anti-convulsant. Figure 1 summarizes various synthetic strategies for thiazolidinone derivatives and their biological significance. On the other hand, the structure of various pharmacologically active agents can be modified by using functional groups. With these functional group studies, prodrug strategies can be successfully applied to a wider range of drug molecules.

Various synthetic strategies for  thiazolidinone derivatives as well as their biological significance Figure 1. Various synthetic strategies for thiazolidinone derivatives as well as their biological significance[1].

Thiazolines are widely used in many fields as raw materials of various materials and pharmaceuticals. In organic synthesis, thiazoline can be used to synthesize 2-methyl-4-isothiazolin-3-one (MIT) preservatives, which can be added to cosmetics and detergents. In terms of drugs, benzisothiazolinone (BIT) has the advantages of broad antibacterial spectrum, high antibacterial activity, low toxicity, and environmental friendliness, and is expected to be an excellent agent for the prevention and treatment of tussah empty carcass disease.

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References

  1. Manjal, S.K. et al. Synthetic and medicinal perspective of thiazolidinones: A review. Bioorganic Chemistry. 2017, 75: 406-423.
  2. Vivekkumar, K. et al. Chapter 4 - Approaches for Prodrugs. Prodrug Design. 2015, 33-49.
  3. Yang, J.C. et al. Evaluation of the Control Effect of Benzisothiazolinone on Streptococcus Pernyi. Acta Sericologica Sinica. 2022, 48(01): 55-61.

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