1593-60-8Relevant articles and documents
Iron(ii)-catalyzed intermolecular aziridination of alkenes employing hydroxylamine derivatives as clean nitrene sources
Berhal, Farouk,Grimaud, Laurence,Kirby, Georgina,Prestat, Guillaume,Vitale, Maxime R.
supporting information, p. 9428 - 9432 (2021/12/09)
The iron-catalyzed intermolecular aziridination of alkenes with hydroxylamine derivatives is described. Using simple iron(ii) sources and readily available ligands, the formal (2 + 1) cycloaddition process proved to be efficient on both styrenes and aliphatic alkenes, providing access to a wide range of aziridines. In these particularly sustainable reaction conditions, yields up to 89% could be obtained, with a catalyst loading which could be lowered to 5 mol% when the reaction was performed on large scale. Preliminary mechanistic studies suggest that both concerted and stepwise pathways are operating in this transformation. This journal is
An Effective Method for the Synthesis of 1,3-Dihydro-2H-indazoles via N-N Bond Formation
Zhang, Xiaoke,Pan, Yang,Liang, Peng,Ma, Xiaofeng,Jiao, Wei,Shao, Huawu
supporting information, p. 5552 - 5557 (2019/11/22)
The [4+1] cycloaddition reaction of bifunctional amino reagents has been achieved with in situ formed aza-ortho-quinone methides. Specifically, N-(tosyloxy)carbamates were used as an N1 synthon and bifunctional amino reagents for this transformation, which provides a metal-free, catalyst-free, and oxidant-free strategy to form nitrogen-nitrogen bonds. (Figure presented.).
DUAL AGONISTS OF FXR AND PPARδ AND THEIR USES
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Page/Page column 41; 71, (2019/04/16)
The present invention relates to small molecule compounds and their use as agonists of farnesoid X receptor (FXR) and/or peroxisome proliferator activated receptor delta (PPARδ). The present invention also relates to the use of said compounds in the treatment of metabolic diseases and respective methods of treatment.
Nondirected, cu-catalyzed sp3 C-H aminations with hydroxylamine-based amination reagents: Catalytic and mechanistic studies
Wang, Anqi,Venditto, Nicholas J.,Darcy, Julia W.,Emmert, Marion H.
supporting information, p. 1259 - 1268 (2017/05/29)
This work demonstrates the use of hydroxylamine-based amination reagents RSO2NH-OAc for the nondirected, Cu-catalyzed amination of benzylic C-H bonds. The amination reagents can be prepared on a gram scale, are benchtop stable, and provide benzylic C-H amination products with up to 86% yield. Mechanistic studies of the established reactivity with toluene as substrate reveal a ligand-promoted, Cu-catalyzed mechanism proceeding through Ph-CH2(NTsOAc) as a major intermediate. Stoichiometric reactivity of Ph-CH2(NTsOAc) to produce Ph-CH2-NHTs suggests a two-cycle, radical pathway for C-H amination, in which the decomposition of the employed diimine ligands plays an important role.
Thienopyrimidine derivative, preparation method thereof and application thereof in medicines
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Paragraph 0175; 0176; 0177, (2016/10/17)
The invention provides a thienopyrimidine derivative, a preparation method thereof and an application thereof in medicines. Specifically, the invention relates to a compound represented by a formula I, wherein the radicals are defined in the description. The compound is effective tyrosine kinase inhibitors in one category, and is particularly suitable for being used as an EGFR and/or HER2 inhibitor.
The pH of HNO donation is modulated by ring substituents in Piloty's acid derivatives: Azanone donors at biological pH
Sirsalmath, Kiran,Suárez, Sebastián A.,Bikiel, Damián E.,Doctorovich, Fabio
, p. 134 - 139 (2013/02/23)
A group of Piloty's acid (N-hydroxybenzenesulfonamide) derivatives were synthesized and fully characterized in order to assess the rates and pH of HNO (azanone, nitroxyl) donation in aqueous media. The derivatives, with electron-withdrawing and -donating substituents include methyl, nitro, fluoro, tri-isopropyl, trifluoromethyl and methoxy groups. The most interesting modulation observed is the change in pH range in which the compounds are able to donate HNO. UV-visible kinetic measurements at different pH values were used to evaluate the decomposition rate of the donors. A novel technique based on electrochemical measurements using a Co-porphyrin sensor was used to assess the release of HNO as a function of pH, by direct measurement of [HNO]. The results were contrasted with DFT calculations in order to understand the electronic effects exerted by the ring substituents, which drastically modify the pH range of donation. For example, while Piloty's acid donates HNO from pH 9.3, the corresponding fluoro derivative starts donating at pH 4.0.
A straightforward route to piloty's acid derivatives: A class of potential nitroxyl-generating prodrugs
Porcheddu, Andrea,De Luca, Lidia,Giacomelli, Giampaolo
experimental part, p. 2149 - 2153 (2011/03/20)
A series of Piloty's acid derivatives were easily prepared under mild and neutral conditions. The ease of isolation of the final product offers a marked advantage over well-known procedures. This methodology is particularly attractive as it cleanly provided low molecular weight aliphatic sulfohydroxamic acids, which are very interesting for their tendency to generate HNO under physiological conditions. Georg Thieme Verlag Stuttgart.
Mild and efficient Lewis acid-promoted detritylation in the synthesis of N-hydroxy amides: A concise synthesis of (-)-cobactin T
Yang, Shyh-Ming,Lagu, Bharat,Wilson, Lawrence J.
, p. 8123 - 8126 (2008/02/12)
(Chemical Equation Presented) An efficient, high-yielding Lewis acid promoted deprotection of O-trityl hydroxylamine derivatives is described. A range of acid-labile protecting groups, such as N-Boc and O-TBS, were tolerated under these mild conditions. The present method is applicable to the synthesis of a broad range of hydroxylamine derivatives, including N-hydroxy amides (hydroxamic acids), N-hydroxy sulfonamides, and N-hydroxy ureas, which often exhibit significant biological activities. An application of this methodology for a concise synthesis of (-)-Cobactin T (18) is also demonstrated.
Carbonic anhydrase inhibitors. Part 37. Novel classes of isozyme I and II inhibitors and their mechanism of action. Kinetic and spectroscopic investigations on native and cobalt-substituted enzymes
Briganti,Pierattelli,Scozzafava,Supuran
, p. 1001 - 1010 (2007/10/03)
The interaction of Zn(II)- and Co(II)-carbonic anhydrase (CA) with a series of compounds possessing moieties resembling the aromatic sulfonamides, such as sulfamide, sulfamic acid, N-substituted aromatic sulfonamides, sulfenamides, sulfinic and seleninic acids, was investigated using kinetic and spectroscopic techniques. All these compounds inhibit the hydrasic and esterasic activity of the enzyme. Their binding within the active site of isozymes I and II is discussed on the basis of modifications of electronic and 1H-NMR spectra of their adducts with the Co(II) enzyme. Some of these compounds represent novel classes of CA inhibitors, possessing equal or stronger potencies than the prototypical inhibitors, the unsubstituted sulfonamides. Qualitative structure-activity correlations are discussed.
Physical Properties and Various Reactions of Thionitrites and Related Substances
Oae, Shigeru,Shinhama, Koichi,Fujimori, Ken,Kim, Yong Hae
, p. 775 - 784 (2007/10/02)
Several new sulfenyl or sulfonyl derivatives, thionitrates (RSNO2), sulfonyl nitrites (RSO2NO), were successfully isolated by treating corresponding thiols and sulfinic acids with dinitrogen tetraoxide (N2O4).Spectroscopic data of both stable and many rather unstable compounds were determined and compared with those of corresponding alkyl nitrites (RONO) or alkyl nitrates (RONO2).Chemical reactivities of these uncommon, novel S-nitroso and S-nitro compounds were investigated.
