21597-13-7Relevant academic research and scientific papers
1,2,4-Dithiazolidine-3,5-dione as an isocyanate equivalent in the Mitsunobu reaction
Wood, Mark E.,Cane-Honeysett, Daniel J.,Dowle, Michael D.
, p. 2046 - 2047 (2002)
1,2,4-Dithiazolidine-3,5-dione 1 can be used as a nitrogen nucleophile in a modified Mitsunobu procedure to give N-alkylated products 2 which can be converted via isocyanates, into amine derivatives, under very mild conditions.
Insights into the Mechanism of Thiol-Triggered COS/H2S Release from N-Dithiasuccinoyl Amines
Zhou, Shengchao,Mou, Yujie,Liu, Miao,Du, Qian,Ali, Basharat,Ramprasad, Jurupula,Qiao, Chunhua,Hu, Li-Fang,Ji, Xingyue
, p. 8352 - 8359 (2020/09/07)
The hydrolysis of carbonyl sulfide (COS) to form H2S by carbonic anhydrase has been demonstrated to be a viable strategy to deliver H2S in a biological system. Herein, we describe N-dithiasuccinoyl amines as thiol-triggered COS/H2S donors. Notably, thiol species especially GSH and homocysteine can trigger the release of both COS and H2S directly from several specific analogues via an unexpected mechanism. Importantly, two representative analogues Dts-1 and Dts-5 show intracellular H2S release, and Dts-1 imparts potent anti-inflammatory effects in LPS-challenged microglia cells. In conclusion, N-dithiasuccinoyl amine could serve as promising COS/H2S donors for either H2S biological studies or H2S-based therapeutics development.
A new and simple synthesis of sulfonyl ureas from sulfonamides and N-alkyl-1,2,4-dithiazolidine-3,5-diones
Gessner, Richard K.,Chibale, Kelly
experimental part, p. 2839 - 2843 (2010/03/03)
A new, short, and simple synthetic approach to sulfonyl ureas is reported. The method involves the transformation of readily synthesized N-alkyl-1,2,4-dithiazolidine-3,5-diones by reaction with primary sulfonamides. Sulfonyl ureas were obtained in moderat
SAR and 3D-QSAR studies on thiadiazolidinone derivatives: Exploration of structural requirements for glycogen synthase kinase 3 inhibitors
Martinez, Ana,Alonso, Mercedes,Castro, Ana,Dorronsoro, Isabel,Gelpí, J. Luis,Luque, F. Javier,Pérez, Conceptión,Moreno, Francisco J.
, p. 7103 - 7112 (2007/10/03)
The 2,4-disubstituted thiadiazolidinones (TDZD) are described as the first ATP-noncompetitive GSK-3 inhibitors. Following an SAR study about TDZD, different structural modifications in the heterocyclic ring aimed to test the influence of each heteroatom o
Efficient synthesis of 1,2,4-dithiazolidine-3,5-diones [dithiasuccinoyl- amines] from bis(chlorocarbonyl)disulfane plus bis(trimethylsilyl)amines
Barany, Michael J.,Hammer, Robert P.,Merrifield,Barany, George
, p. 508 - 509 (2007/10/03)
The 1,2,4-dithiazolidine-3,5-dione heterocycle, also referred to as a dithiasuccinoyl (Dts)-amine, serves as a readily removable amino protecting group for building blocks used in syntheses of peptides, glycopeptides, and PNA; it is also useful as a masked isocyanate and (inversely) as a sulfurization reagent for trivalent phosphorus. Bis(chlorocarbonyl)disulfane, the two-sulfur analogue of succinyl chloride, has been envisioned as a reagent for facile single-step elaboration of the heterocycle. However, reactions of bis(chlorocarbonyl)disulfane directly with primary amines fail to yield Dts-amines for reasons that are discussed. Inspired by several precedents from the organosilicon chemistry literature that a trimethylsilyl group may serve as a "large proton," a successful, high-yield preparation of Dts-amines through reactions of bis(chlorocarbonyl)disulfane with bis(trimethylsilyl)amines has been developed. Studies aimed at elucidating mechanistic reasons for these observations are also presented. Copyright
A stereocontrolled route to protected isocyanates from alcohols
Cane-Honeysett, Daniel J.,Dowle, Michael D.,Wood, Mark E.
, p. 2141 - 2148 (2007/10/03)
Full details are given for a modified Mitsunobu approach to the formation of N-alkylated 1,2,4-dithiazolidine-3,5-diones 2 from a wide range of alcohols 10 with predominantly, inversion of configuration. The resulting products 2 can be regarded as protected isocyanates 6.
Synthetic and structural studies on 1,2,4-dithiazolidine-3,5-dione derivatives
Wood, Mark E.,Cane-Honeysett, Daniel J.,Dowle, Michael D.,Coles, Simon J.,Hursthouse, Michael B.
, p. 3015 - 3023 (2007/10/03)
Methods have been developed for the N-alkylation of 1,2,4-dithiazolidine-3,5-dione 2 and the subsequent conversion of the N-alkylated derivatives into isocyanates 5. An extension of this methodology onto a solid-support is also reported. X-ray crystallographic analysis has been carried out on potassium 1,2,4-dithiazolidine-3,5-dione 3 for structural comparison with the parent heterocycle 2.
1,2,4-Dithiazolidine-3,5-dione: A nucleophilic isocyanate 'building block'
Cane-Honeysett,Dowle,Wood
, p. 1622 - 1624 (2007/10/03)
Mild conditions are described for the direct N-alkylation of 1,2,4-dithiazolidine-3,5-dione 1 using a variety of alkyl halides with subsequent conversion of the products 2 into alkyl isocyanates using triphenylphosphine.
Efficient Synthesis of 1,2,4-Dithiazolidine-3,5-diones (Dithiasuccinoyl-amines) and Observations on Formation of 1,2,4-Thiadiazolidine-3,5-diones by Related Chemistry
Slomczynska, Urszula,Barany, George
, p. 241 - 246 (2007/10/02)
An efficient synthesis of 1,2,4-dithiazolidine-3,5-diones (1) from chlorocarbonylsulfenyl chloride (3) plus O-dimethylaminoethyl-N-alkyl or aryl thiocarbamates (4) has been worked out.In this synthesis, 1,2,4-thiadiazolidine-3,5-diones (5) have been shown to arise as low-level-by-products, and experiments were conducted to elucidate the mechanism of the side reaction.N,N'-Dimethyl-1,2,4-thiadiazolidine-3,5-dione (5a) was prepared in one step from N,N'-dimethylurea plus 3, or from 4a plus one equivalent of sulfuryl chloride.A general route to 5 involved reaction ofequimolar amounts of isocyanates (6), isothiocyanates (7) and sulfuryl chloride followed by hydrolysis of intermediate 9.Heterocycles reported have been characterized by nmr, ir, uv, ms, and hplc.
