722-27-0Relevant articles and documents
Direct visualization of photo-induced disulfide through oxidative coupling ofpara-aminothiophenol
He, Wei,Xia, Chang,Gao, Peng Fei,Zhou, Jun,Li, Yuan Fang,Huang, Cheng Zhi
, p. 4190 - 4193 (2021)
Chemical transformations under visible irradiation are interesting in green preparation. Herein, a photo-oxidative coupling reaction ofpara-aminothiophenol (p-ATP) dimerizing to 4-aminophenyl disulfide (APDS) rather than 4,4′-dimercaptoazobenzene (DMAB) was achieved in water by visible light irradiation, producing monodispersed organic nanoparticlesin situwith strong light scattering visualized by the dark-field microscopy (DFM) imaging technique, owing to the formation of disulfide.
Practical and efficient recyclable oxidative system for the preparation of symmetrical disulfides under aerobic conditions
Ling, Ong Chiu,Heidelberg, Thorsten,Ching, Juan Joon,Khaligh, Nader Ghaffari
, p. 281 - 294 (2020/12/13)
An efficient and practical oxidative coupling of thiols to symmetrical disulfides is developed at room temperature under aerobic conditions. The commercially available sodium methoxide solution 30 wt. % in methanol together with the air was used as a retrievable promoter system and green oxidant, respectively, for the preparation of symmetrical disulfides. The desired products were obtained in good to high yields by an economical procedure. No overoxidation of the symmetrical disulfides was observed, and various functional groups were well tolerated in the current protocol. Moreover, the new reagent reduces the generation of hazardous waste due to its high reusability. The reaction proceeded in the absence of light, and it was not inhibited by TEMPO. Also, the low yield of TEMPO-benzyl thiol adduct was detected under these conditions. Based on our experiments, a possible mechanism was proposed in the absence and presence of TEMPO.
Synthesis and biological evaluation of disulfides as anticancer agents with thioredoxin inhibition
Wei, Xiangxu,Zhong, Miao,Wang, Song,Li, Lexun,Song, Zi-Long,Zhang, Junmin,Xu, Jianqiang,Fang, Jianguo
, (2021/03/24)
Altered redox homeostasis as a hallmark of cancer cells is exploited by cancer cells for growth and survival. The thioredoxin (Trx), an important regulator in maintaining the intracellular redox homeostasis, is cumulatively recognized as a promising target for the development of anticancer drugs. Herein, we synthesized 72 disulfides and evaluated their inhibition for Trx and antitumor activity. First, we established an efficient and fast method to screen Trx inhibitors by using the probe NBL-SS that was developed by our group to detect Trx function in living cells. After an initial screening of the Trx inhibitory activity of these compounds, 8 compounds showed significant inhibition activity against Trx. We then evaluated the cytotoxicity of these 8 disulfides, compounds 68 and 69 displayed high cytotoxicity to HeLa cells, but less sensitive to normal cell lines. Next, we performed kinetic studies of both two disulfides, 68 had faster inhibition of Trx than 69. Further studies revealed that 68 led to the accumulation of reactive oxygen species and eventually induced apoptosis of Hela cells via inhibiting Trx. The establishment of a method for screening Trx inhibitors and the discovery of 68 with remarkable Trx inhibition provide support for the development of anticancer candidates with Trx inhibition.
Simultaneous Formation of a Fully Organic Triply Dynamic Combinatorial Library
Drozdz, Wojciech,Stefankiewicz, Artur R.,Walczak, Anna
supporting information, p. 3641 - 3645 (2021/05/29)
Here we report the simultaneous formation of doubly and triply dynamic libraries as a result of exchange reactions between functionalized organic building blocks. A combination of three different reversible covalent linkages involving a boronate ester transesterification along with an imine and disulfide exchange was employed to generate a new type of fully organic triply dynamic molecular assembly.
Green Aerobic Oxidation of Thiols to Disulfides by Flavin-Iodine Coupled Organocatalysis
Iida, Hiroki,Kozako, Ryo,Oka, Marina
supporting information, p. 1227 - 1230 (2021/06/21)
Coupled catalysis using a riboflavin-derived organocatalyst and molecular iodine successfully promoted the aerobic oxidation of thiols to disulfides under metal-free mild conditions. The activation of molecular oxygen occurred smoothly at room temperature through the transfer of electrons from the iodine catalyst to the biomimetic flavin catalyst, forming the basis for a green oxidative synthesis of disulfides from thiols.
Dimsyl Anion Enables Visible-Light-Promoted Charge Transfer in Cross-Coupling Reactions of Aryl Halides
Cooke, Maria Victoria,Laulhé, Sébastien,Pan, Lei,Spencer, Amara
supporting information, (2021/11/01)
A methodology is reported for visible-light-promoted synthesis of unsymmetrical chalcogenides enabled by dimsyl anion in the absence of transition-metals or photoredox catalysts. The cross-coupling reaction between aryl halides and diaryl dichalcogenides proceeds with electron-rich, electron-poor, and heteroaromatic moieties. Mechanistic investigations using UV-Vis spectroscopy, time-dependent density functional theory (TD-DFT) calculations, and control reactions suggest that dimsyl anion forms an electron-donor-acceptor (EDA) complex capable of absorbing blue light, leading to a charge transfer responsible for generation of aryl radicals from aryl halides. This previously unreported mechanistic pathway may be applied to other light-induced transformations performed in DMSO in the presence of bases and aryl halides.
Adsorption of rhodamine B by organic porous materials rich in nitrogen, oxygen, and sulfur heteroatoms
Du, Xiao-Cheng,Zhu, Ji-Hua,Quan, Zheng-Jun,Wang, Xi-Cun
supporting information, p. 3448 - 3453 (2021/03/03)
Rhodamine B is a non-degradable carcinogenic dye, so it is of great significance to remove rhodamine B from wastewater. We designed and prepared a novel porous organic polymer adsorbent (DAPS-TP-POP), which contains abundant N, O, and S heteroatoms. DAPS-TP-POP was characterized through FT-IR, PXRD, TGA, TEM, BET etc. The results show that DAPS-TP-POP has high stability and abundant heteroatoms. DAPS-TP-POP has good adsorption capacity for rhodamine B. Besides, it also shows excellent recyclability.
Accelerated reduction and solubilization of elemental sulfur by 1,2-aminothiols
Stoffel, Jonathan T.,Riordan, Kimberly T.,Tsui, Emily Y.
supporting information, p. 12488 - 12491 (2021/12/04)
Nucleophilic 1,2-aminothiol compounds readily reduce typically-insoluble elemental sulfur to polysulfides in both water and nonpolar organic solvents. The resulting anionic polysulfide species are stabilized through hydrogen-bonding interactions with the proximal amine moieties. These interactions can facilitate sulfur transfer to alkenes.
Synthetic method of diaryl disulfide compound
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Paragraph 0036-0045, (2020/11/23)
The invention relates to a synthetic method of a diaryl disulfide compound. The method comprises the following steps of: in an organic solvent, under the condition of nitrogen, using arylboronic acidand sulfur as the reaction raw materials, carrying out free radical vulcanization/self-polymerization coupling reaction under the action of a transition metal silver catalyst to obtain the diaryl disulfide compound. The method is simple in reaction condition, simple and convenient in experimental operation and high in product yield and purity, opens up a synthetic route and method for preparationof the diaryl disulfide compound, and has good application potential and research value.
In Situ Coupling of Single Molecules Driven by Gold-Catalyzed Electrooxidation
Zang, Yaping,Stone, Ilana,Inkpen, Michael S.,Ng, Fay,Lambert, Tristan H.,Nuckolls, Colin,Steigerwald, Michael L.,Roy, Xavier,Venkataraman, Latha
supporting information, p. 16008 - 16012 (2019/07/16)
A single-molecule method has been developed based on the scanning tunneling microscope (STM) to selectively couple a series of aniline derivatives and create azobenzenes. The Au-catalyzed oxidative coupling is driven by the local electrochemical potential at the nanostructured Au STM tip. The products are detected in situ by measuring the conductance and molecular junction elongation and compared with analogous measurements of the expected azobenzene derivatives prepared ex situ. This single-molecule approach is robust, and it can quickly and reproducibly create reactions for a variety of anilines. We further demonstrate the selective synthesis of geometric isomers and the assembly of complex molecular architectures by sequential coupling of complementary anilines, demonstrating unprecedented control over bond formation at the nanoscale.
