Thiazolidinone derivatives

CycUzation of thiosemicarbazide 14 with chloroacetylchloride in chloroform afforded thiazolidinone derivative 22 (Scheme 5). 

Alkyl- and aryl-substituted furo[2,3- / thiazolidine derivatives 279, with potential biological activity, have been synthesized by the reaction of methoxycarbonylmethylenetriphenylphosphorane with 4-thiazolidinone derivatives... 

Some of the other scaffolds used to synthetize Kvl.5 channel inhibitors are prototypes of vicinally substituted heterocycles, such as the tetrazole 2f shown in Table 1. This series was developed to circumvent a metabolic liability of thiazolidinone derivatives previously identified as potent Kvl.5 blockers [54]. Some chemistry efforts have been directed toward novel structures that provide practical advantages in addition to Kvl.5 potency. This is the case of Kvl.5 inhibitors based on a diisopropyl amide scaffold [50]. 

The chemistry of 4-thiazolidinones (1) was reviewed in depth by Brown in 1962.1 Since then, largely due to the wide variety of physiological activity demonstrated by this class of compounds, several thousand papers2 on the chemistry of 4-thiazolidinone derivatives, exclusive of rhodanine derivatives, have been published. This review will consider only the important literature highlights of 1, 2,4-thiazolidinediones (2), 2-imino-4-thiazolidinones (3), and 4-oxo-2-thiazolin-2-ylhydrazones (4). Neither rhodanine (5) nor the extensive patent and obscure literature references dealing with 4-thiazolidinones will be considered in any detail within this review. 

Thione adds to the unsaturated carbon—carbon linkage of maleic anhydride probably by a Michael-type reaction, subsequent cyclization results in the synthesis of 4-thiazolidinone derivatives. The reaction of thi-... 

Zhou, H., Wu, S., Zhai, S., Liu, A., Sun, Y.. Li, R. et al. (2008) Design, synthesis, cytoselective toxicity, structure-activity relationships and pharmacophores of thiazolidinone derivatives targeting drug-resistant lung cancer cells. 

Carbon-13 and H NMR spectroscopy have been employed for conformational studies of some thiazolidinone derivatives <83MI 306-01,92T7157> as discussed in Section 3.06.3.6.1. A similar study was carried out with penicillin sulfoxide derivatives <9iCJC578>. 

Rane RA, Sahu NU, Shah CP. Synthesis and antibiofihn activity of marine natural product-based 4-thiazolidinones derivatives. Bioorg Med Chem Lett 2012 22 (23) 7131. ... 

Recent developments and biological activities of thiazolidinone derivatives 12BMC3378. 

Thiazolidine-derived enamines 155 led to thio-substi-tuted bicyclic 1,4-dihydropyridine derivatives 156 in good to excellent yields [65]. A 4CR using thiazolidinone-derived enamines 158 gave the arylidene-substituted products 159/160 (Scheme 13.39) [66]. 

Green Chemistry Conventional and Microwave-Induced Synthesis of Various Thiazolidinone Derivatives from 3- [(lE)-(2 -chloro-7 -methoxyquinoline-3 -yl)methylene]amino -4-... 

In the course of development research, we inquired into the structure-activity relationships of the corresponding thiazolidinone derivatives. First, in order to confirm the role of the methyl group at the 4-position in trans stereoconfiguration to the phenyl group at the 5-position, the following matters were investigated. 

An efficient and extremely fast method for the synthesis of some thiazolidinone derivatives from benzotriazole has been reported under microwave irradiation (Shri-mali et al., 2009). 

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