2682-49-7Relevant articles and documents
One-step synthesis of 2-thiazolidinone
Shen, Li Hong,Wang, Hai Xian,Zhang, Le,Zhang, Jun
, p. 939 - 940 (2014)
An efficient and direct access to thiazolidinone is developed. 2-Thiazolidinone is synthesized by urea and 2-Aminoethylmercaptan hydrochloride and this one-step process proceeds with good yields, under mild conditions. The structure of the compound was confirmed by IR, 1H NMR, MS and the product purity was 98 % by HPLC.
Thiazolidine prodrugs as protective agents against γ-radiation-induced toxicity and mutagenesis in V79 cells
Wilmore,Cassidy,Warters,Roberts
, p. 2661 - 2666 (2001)
Representatives of two classes of thiazolidine prodrug forms of the well-known radioprotective agents L-cysteine, cysteamine, and 2-[(aminopropyl)amino]ethanethiol (WR-1065) were synthesized by condensing the parent thiolamine with an appropriate carbonyl donor. Inherent toxicity of the prodrugs was assessed in V79 cells using a clonogenic survival assay. Protection against radiation-induced cell death was measured similarly after exposure to 0-8 Gy γ (137Cs) radiation. Antimutagenic activity was determined at the hypoxanthine-guanine phosphoribosyltransferase (HGPRT) locus. All thiazolidine prodrugs exhibited less toxicity than their parent thiolamines, sometimes dramatically so. Protection against radiation-induced cell death was observed for the 2-alkylthiazolidine, 2(R,S)-D-ribo-(1′,2′,3′,4′-tetrahydroxybutyl) thiazolidine (RibCyst), which produced a protection factor at 8 Gy of 1.8; the cysteine analogue, 2(R,S)-D-ribo-(1′,2′,3′,4′-tetrahydroxybutyl) thiazolidine-4(R)-carboxylic acid (RibCys), was less active. RibCyst also exhibited excellent antimutational activity, rivaling that of WR-1065. The 2-oxothiazolidine analogues showed little activity in either determination under the conditions tested, perhaps due to their enhanced chemical and biochemical stability.
Concise and Additive-Free Click Reactions between Amines and CF3SO3CF3
Song, Hai-Xia,Han, Zhou-Zhou,Zhang, Cheng-Pan
supporting information, p. 10907 - 10912 (2019/08/02)
Trifluoromethyl trifluoromethanesulfonate has proved to be an excellent reservoir of difluorophosgene and a promising click ligation for amines in the preparation of urea derivatives, heterocycles, and carbamoyl fluorides under metal- and additive-free conditions. The reactions are rapid, efficient, selective, and versatile, and can be performed in benign solvents, giving products in excellent yields with minimal efforts for purification. The characteristics of the reactions meet the requirements of a click reaction. The use of trifluoromethyl trifluoromethanesulfonate as a click reagent is advantageous over other “CO” sources (e.g., TsOCF3, PhCO2CF3, CsOCF3, AgOCF3, and triphosgene) because this reagent is readily accessible; easy to scale up; and highly reactive, even under metal- and additive-free conditions. It is anticipated that CF3SO3CF3 will be increasingly as important as SO2F2 as a click agent in future drug design and development.
Exploring hydrogen peroxide responsive thiazolidinone-based prodrugs
Perez, Christian,Monserrat, Jean-Philippe,Chen, Yao,Cohen, Seth M.
supporting information, p. 7116 - 7119 (2015/04/27)
A novel approach for developing prodrugs based on masked carboxylic acids is described. Rather than using conventional esterase-based activation, thiazolidinone protecting groups have been identified that can reveal carboxylic acid groups upon activation by hydrogen peroxide. This may prove valuable in the continuing development of prodrug strategies that rely on reactive oxygen species (ROS) as a trigger. This journal is
REACTIVE OXYGEN SPECIES-BASED PRODRUGS
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Paragraph 0273, (2015/02/05)
Provided herein are ROS-sensitive prodrug compositions and methods of treating ROS-associated diseases by administering the ROS-sensitive prodrug compositions.
A convenient synthesis of thiazolidin-2-ones from thiazolidine-2-thiones: Antibiotic activity and revisiting the mechanism
Deng, Xiaobing,Chen, Ning,Wang, Zhixin,Li, Xinyao,Hu, Hongyan,Xu, Jiaxi
experimental part, p. 1563 - 1571 (2011/10/03)
Various substituted thiazolidin-2-ones were synthesized from the corresponding thiazolidine-2-thiones with bromoethanol in ethanol with sodium ethoxide as a base. The optimal reaction conditions and mechanism were reinvestigated in detail. The bioassay indicated that (S)-4-isobutyl and (S)-4-benzylthiazolidin-2-ones show certain inhibitive activities against Candida albicans and Escherichia coli. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
Modified Mg: Al hydrotalcite in the synthesis of oxazolidin-2-ones
Cwik, Agnieszka,Fuchs, Aliz,Hell, Zoltan,Boejtoes, Ildiko,Halmai, Dora,Bombicz, Petra
, p. 967 - 969 (2007/10/03)
The modified Mg: Al (3: 1) hydrotalcite has been found to be an efficient catalyst in the conversion of carbamates into oxazolidin-2-ones under mild reaction conditions. A wide variety of oxazolidin-2-ones were obtained with excellent chemical yield. The Royal Society of Chemistry 2005.
HETEROCYCLIC MODULATORS OF NUCLEAR RECEPTORS
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, (2008/06/13)
Compounds, compositions and methods for modulating the activity of nuclear receptors are provided. In particular, heterocyclic compounds are provided for modulating the activity of farnesoid X receptor (FXR), liver X receptor (LXR) and/or orphan nuclear receptors. In certain embodiments, the compounds are thiazolidinone derivatives.
Prodrugs and conjugates of thiol-and selenol-containing compounds and methods of use thereof
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Page 5, (2008/06/13)
Disclosed is a prodrugs of the formula: where A is a sulfur or a selenium, and R is derived from a mono- di- or oligo- saccharide. Also disclosed is a prodrug of the formulas; where A is sulfur or selenium, R′ is derived from a sugar and R′ has the formula (CHOH)nCH2OH, where n is 1 to 5, or R′ is an alkyl or aryl group, or R′ is ═O, and the R″ groups may be the same or different and may be hydrogen, alkyl, alkoxy, carboxy. Also disclosed is a conjugate of an antioxidant vitamin and a thiolamine or selenolamine. Also disclosed is a prodrug of the formula; where A is sulfur or selenium, and R′ is derived from a sugar and R′ has the formula (CHOH)nCH2OH, where n is 1 to 5, or R′ is also be an alkyl or aryl group, or R′ is ═O, and R?is an alkoxy, or an amine group. Also disclosed is a prodrug of the formula: R is COOH or H, and R′ is derived from a sugar and R′ has the formula (CHOH)nCH2OH, where n is 1 to 5, or R′ is an alkyl or aryl group, or R′ is ═O.
Synthesis of 2-oxazolidones by sulfur-assisted thiocarboxylation with carbon monoxide and oxidative cyclization with molecular oxygen under mild conditions
Mizuno, Takumi,Takahashi, Junko,Ogawa, Akiya
, p. 7805 - 7808 (2007/10/03)
Simple synthetic method on 2-oxazolidone derivatives was established. 2-Aminoethanols were easily subjected to the thiocarboxylation with carbon monoxide promoted by elemental sulfur, followed by the oxidative cyclization with molecular oxygen to give corresponding 2-oxazolidones in good yields under mild conditions (1 atm, rt). Furthermore, 2-imidazolidones and 2-thiazolidone were also prepared in good yields similarly.
