- One-step synthesis of 2-thiazolidinone
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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.
- Shen, Li Hong,Wang, Hai Xian,Zhang, Le,Zhang, Jun
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- Thiazolidine prodrugs as protective agents against γ-radiation-induced toxicity and mutagenesis in V79 cells
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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.
- Wilmore,Cassidy,Warters,Roberts
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- Concise and Additive-Free Click Reactions between Amines and CF3SO3CF3
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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.
- Song, Hai-Xia,Han, Zhou-Zhou,Zhang, Cheng-Pan
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supporting information
p. 10907 - 10912
(2019/08/02)
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- Exploring hydrogen peroxide responsive thiazolidinone-based prodrugs
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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
- Perez, Christian,Monserrat, Jean-Philippe,Chen, Yao,Cohen, Seth M.
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supporting information
p. 7116 - 7119
(2015/04/27)
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- REACTIVE OXYGEN SPECIES-BASED PRODRUGS
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Provided herein are ROS-sensitive prodrug compositions and methods of treating ROS-associated diseases by administering the ROS-sensitive prodrug compositions.
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Paragraph 0273
(2015/02/05)
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- A convenient synthesis of thiazolidin-2-ones from thiazolidine-2-thiones: Antibiotic activity and revisiting the mechanism
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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.
- Deng, Xiaobing,Chen, Ning,Wang, Zhixin,Li, Xinyao,Hu, Hongyan,Xu, Jiaxi
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experimental part
p. 1563 - 1571
(2011/10/03)
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- Modified Mg: Al hydrotalcite in the synthesis of oxazolidin-2-ones
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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.
- Cwik, Agnieszka,Fuchs, Aliz,Hell, Zoltan,Boejtoes, Ildiko,Halmai, Dora,Bombicz, Petra
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p. 967 - 969
(2007/10/03)
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- HETEROCYCLIC MODULATORS OF NUCLEAR RECEPTORS
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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.
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- Prodrugs and conjugates of thiol-and selenol-containing compounds and methods of use thereof
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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.
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- Synthesis of 2-oxazolidones by sulfur-assisted thiocarboxylation with carbon monoxide and oxidative cyclization with molecular oxygen under mild conditions
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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.
- Mizuno, Takumi,Takahashi, Junko,Ogawa, Akiya
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p. 7805 - 7808
(2007/10/03)
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- Liquid phase parallel synthesis of chemical libraries
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This invention features methods of biphasic synthesis for synthesizing combinatorial libraries and combinatorial libraries of chemical compounds utilizing the template, and combinatorial libraries of chemical compounds formed by the methods of this invention.
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- Investigations on 1,3-Thiazines, 43. - Newman-Kwart Rearrangement in the Course of Thiocarbazoylation of Tetrahydro-2H-1,3-thiazin-2-one and Thiazolidin-2-one
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Thiocarbazoylation of tetrahydro-2H-1,3-thiazin-2-one (1) with thiocarbazic acid chlorides leads to N-thiocarbazoyl derivatives 5 and N-carbazoyl-tetrahydro-2H-1,3-thiazin-2-thiones 8, which are interpreted as products of an O-thiocarbazoylation to 6, subsequent Newman-Kwart rearrangement to 7 and final S->N transcarbazoylation.Thiocarbazoylation of thiazolidin-2-one (9) yields an isolable Newman-Kwart rearrangement product 12 and its product 13 of S->N transcarbazoylation.
- Hanefeld, Wolfgang,Goesseln, Hans Joachim
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p. 405 - 407
(2007/10/02)
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- A NEW SYNTHESIS OF HETEROCYCLES VIA CARBONILATION OF AMINES WITH CARBON MONOXIDE IN THE PRESENCE OF SELENIUM
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Amines which contain a second functional group in the appropriate position react with carbon monoxide in the presence of selenium to form heterocyclic derivatives in which carbon monoxide is incorporated.For instance, diamines, aminoalcohols, and their related compounds undergo carbonylation to give cyclic ureas, urethanes and the corresponding carbonylated compounds.For diamines and amino alcohols with more than two carbon atoms between the functional groups, intermolecular carbonylative coupling takes place competing with the intramolecular reaction.High selectivity has been attained under specified reaction conditions.Anilines having cyano or acetyl groups on the ortho position afford new classes of selenium-containing heterocycles.In these reactions, carbamoselenoate has been suggested as the common key intermediate.
- Yoshida, Tohru,Kambe, Nobuaki,Ogawa, Akiya,Sonoda, Noboru
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p. 137 - 148
(2007/10/02)
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- A FACILE SYNTHESIS OF 2-OXO-THIAZOLIDINES OF BIOLOGICAL INTEREST.
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A facile procedure for the preparation in good yield of L-2-oxothiazolidine-4-carboxylic acid and other 2-oxothiazolidines of biological interest is described, involving reaction of suitable aminothiols with 1,1'-carbonyldiimidazole in an organic solvent.
- d'Ischia, M.,Prota, G.,Rotteveel, R. C.,Westerhof, W.
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p. 1577 - 1586
(2007/10/02)
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- Organophosphorus compound and insecticidal, miticidal or nematicidal composition containing it
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An organophosphorus compound represented by the general formula: STR1 where each of X1 and X3 is a hydrogen atom; an alkyl or alkoxy group which may be substituted by halogen, alkoxy, alkylthio, phenoxy, halogenated phenoxy, phenylthio or halogenated phenylthio; a carboxyl group; an alkoxycarbonyl group; or a phenyl group which may be substituted by halogen, each of X2 and X4 is a hydrogen atom or an alkyl group, provided that X2 and X3 may together form an alkylene group, each of Y1, Y2 and Z is an oxygen atom or a sulfur atom, and each of R1 and R2 is an alkyl group.
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- Processes for the production of heterocyclic compounds
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A ketonic heterocyclic compound having at least two heteroatoms in the ring is prepared by reacting a difunctional compound having the general formula STR1 in which R1, R2, R3 and R4 are members of the group consisting of aliphatic, aromatic, cycloaliphatic and heterocyclic hydrocarbons which may contain functional groups selected from --OH, --OR5, --COOH, --COOR5, --CN, --Cl, --Br, --I, --F, and --CO--R5, wherein R5 is an aliphatic, aromatic, cycloaliphatic or heterocyclic hydrocarbon; X is oxygen or sulphur; Y is sulphur or nitrogen; n is an integer ranging from 1 to 3, or zero; R6 is a hydrogen or a hydrocarbon radical included in the above definition of R1 R2 R3 and R4 ; and m is the valence of Y, with carbon monoxide and oxygen in the presence of a catalyst selected from selenium, selenium compounds and complexes of copper, in the temperature range of from room temperature to 80° C and in the pressure range of from 1 to 10 atmospheres.
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