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1,3-Thiazolidin-4-ones: Biological Potential, History, Synthetic Development and Green Methodologies

[ Vol. 15 , Issue. 8 ]

Author(s):

Jonas da Silva Santos, Joel Jones Junior* and Flavia M. da Silva*   Pages 1109 - 1123 ( 15 )

Abstract:


Background: We present here the synthesis of 1,3-thiazolidin-4-one (1) and its functionalised analogues, such as the classical isosteres, glitazone (1,3-thiazolidine-2,4-dione) (2), rhodanine (2-thioxo-1,3- thiazolidin-4-one) (3) and pseudothiohydantoin (2-imino-1,3-thiazolidin-4-one) (4) started in the midnineteenth century to the present day (1865-2018).

Objective: The review focuses on the differences in the representation of the molecular structures discussed here over time since the first discussions about the structural theory by Kekulé, Couper and Butlerov. Moreover, advanced synthesis methodologies have been developed for obtaining these functional group, including green chemistry. We discuss about its structure and stability and we show the great biological potential.

Conclusion: The 1,3-thiazolidin-4-one nucleus and functionalised analogues such as glitazones (1,3- thiazolidine-2,4-diones), rhodanines (2-thioxo-1,3-thiazolidin-4-ones) and pseudothiohydantoins (2-imino-1,3- thiazolidine-2-4-ones) have great pharmacological importance, and they are already found in commercial pharmaceuticals. Studies indicate a promising future in the area of medicinal chemistry with potential activities against different diseases. The synthesis of these nuclei started in the mid-nineteenth century (1865), with the first discussions about the structural theory by Kekulé, Couper and Butlerov. The present study has demonstrated the differences in the representations of the molecular structures discussed here over time. Since then, various synthetic methodologies have been developed for obtaining these nuclei, and several studies on their structural and biological properties have been performed. Different studies with regards to the green synthesis of these compounds were also presented here. This is the result of the process of environmental awareness. Additionally, the planet Earth is already showing clear signs of depletion, which is currently decreasing the quality of life.

Keywords:

1, 3-Thiazolidin-4-one, glytazone, 1, 3-thiazolidine-2, 4-dione, rhodamine, 2-thioxo-1, 3-thiazolidin-4-one, pseudohydantoin, 2- imino-1, 3-thiazolidin-4-one, green chemistry.

Affiliation:

Sintese Organica Ambiental SOA - Dept. Quimica Organica - Instituto de Quimica – UFRJ - CP 68.584, 21941-972, Rio de Janeiro, RJ, Sintese Organica Ambiental SOA - Dept. Quimica Organica - Instituto de Quimica – UFRJ - CP 68.584, 21941-972, Rio de Janeiro, RJ, Sintese Organica Ambiental SOA - Dept. Quimica Organica - Instituto de Quimica – UFRJ - CP 68.584, 21941-972, Rio de Janeiro, RJ



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