Synthesis of N-substituted 2,4-thiazolidinediones from oxazolidinethiones

Mendoza, Guadalupe; Hernández, Hector; Quintero, Leticia; Sosa-Rivadeneyra, Martha; Bernès, Syl­vain; Sansinenea, Estibaliz

doi:10.1016/j.tetlet.2005.09.116

Cited by 13 publications

(2 citation statements)

References 16 publications

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“…Isopropyl derivatives were higher in yield than unsubstituted ones (Scheme 51). [150] In the same manner described above, 5-substituted-1,3,4oxadiazole-2-thione ring 169 has been converted to corresponding 3-substituted acetamido-2,4-thiazolidinedione 170 by reaction with chloroacetic acid (Scheme 52). [151] Also, the addition of phenyl isothiocyanate 46 to N-phenyl derivatives of pseudothiohydantoin 171 a-i forms 2-phenylthiocarbamoylimino-3-aryl-4-oxothiazolidines 174 a-i.…”

Section: By Ring-opening Ring-closure (Rorc) Transformationmentioning

confidence: 99%

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

et al. 2023

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Thiazolidinedione (TZD) is one of the privileged heterocyclic rings and has shown many biological applications in medicinal chemistry and drug discovery. This review covers the synthetic approaches of TZD and its derivatives, different synthetic techniques for affording the desired regioselectivity and stereoselectivity, and the techniques that would enhance reaction conditions such as microwave, one‐pot, or ultrasound synthesis. It focuses on synthetic challenges of glitazones and the transformation of other heterocycles to TZD. Moreover, the chemical and biological behavior of TZD through the substitution in the N3 position, modification of the C5 position, annealing in complex heterocyclic systems, and hybridization with other pharmacologically attractive moieties are discussed. All reactions mentioned are provided as possible with different reaction conditions, mechanisms, derivatives scope, yield and clarified by applications of such reactions in the construction of potential medicinal agents. The review also answers questions about rapid racemization of glitazones, their toxicity, considering TZD as pan‐assay interference compounds (PAINS) or not, and the influence of saturation of 5‐position of TZD in their biological activities. This review is a comprehensive guide to make informed decisions for construction of TZD derivatives with biological potentials.

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Section: By Ring-opening Ring-closure (Rorc) Transformationmentioning

confidence: 99%

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

et al. 2023

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“…The product ( 24 ), was generated as an oil in 67 % yield (Scheme 10). [25] …”

Section: Substitution Reactionsmentioning

confidence: 99%

Thiazolidinediones: An In–Depth Study of Their Synthesis and Application to Medicinal Chemistry in the Treatment of Diabetes Mellitus

2021

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2,4‐Thiazolidinedione (TZD) is a privileged and highly utilised scaffold for the development of pharmaceutically active compounds. This sulfur‐containing heterocycle is a versatile pharmacophore that confers a diverse range of pharmacological activities. TZD has been shown to exhibit biological action towards a vast range of targets interesting to medicinal chemists. In this review, we attempt to provide insight into both the historical conventional and the use of novel methodologies to synthesise the TZD core framework. Further to this, synthetic procedures utilised to substitute the TZD molecule at the activated methylene C5 and N3 position are reviewed. Finally, research into developing clinical agents, which act as modulators of peroxisome proliferator‐activated receptors gamma (PPARγ), protein tyrosine phosphatase 1B (PTP1B) and aldose reductase 2 (ALR2), are discussed. These are the three most targeted receptors for the treatment of diabetes mellitus (DM).

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