- Cu-Catalyzed Electrophilic Disulfur Transfer: Synthesis of Unsymmetrical Disulfides
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An efficient electrophilic persulfuration reaction leading to unsymmetrical disulfides and polysulfides has been developed. Various nucleophiles, including aryl boronic acids, β-keto esters, and thiols, can be used as substrates. The notable features of t
- Wang, Weiguo,Lin, Yunzhi,Ma, Yudao,Tung, Chen-Ho,Xu, Zhenghu
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- Synthesis and biological evaluation of disulfides as anticancer agents with thioredoxin inhibition
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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.
- Wei, Xiangxu,Zhong, Miao,Wang, Song,Li, Lexun,Song, Zi-Long,Zhang, Junmin,Xu, Jianqiang,Fang, Jianguo
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- Visible-light photocatalytic selective aerobic oxidation of thiols to disulfides on anatase TiO2
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This work presents the visible-light photocatalytic selective oxidation of thiols to disulfides with molecular oxygen (O2) on anatase TiO2. The high specific surface area of anatase TiO2 proved to be especially critical in
- Xu, Hui,Shi, Ji-Long,Lyu, Shaoshuai,Lang, Xianjun
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p. 1468 - 1473
(2020/04/29)
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- TEMPO visible light photocatalysis: The selective aerobic oxidation of thiols to disulfides
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TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl) is well-established in orangocatalysis that usually work in synergy with transition-metal catalysis or semiconductor photocatalysis. Here, TEMPO was turned into a visible light photocatalyst to conduct the selective aerobic oxidation of thiols into disulfides. With O2 as an oxidant, a mild and efficient protocol for the selective oxidation of thiols into disulfides including symmetrical and unsymmetrical ones with 5 molpercent of TEPMO as a photocatalyst was developed at room temperature under the irradiation of 460 nm blue LEDs. It was found that a complex formed between TEMPO and thiols underpinned the visible light activity and disulfides were obtained in very high isolated yields. This work suggests that TEMPO takes diverse roles in for photocatalytic selective oxidative transformations with O2 as the oxidant.
- Xu, Hui,Zhang, Yu-Fei,Lang, Xianjun
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supporting information
p. 1520 - 1524
(2019/12/09)
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- T BuOK-triggered bond formation reactions
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Recently, inexpensive and readily available tBuOK has seen widespread use in transition-metal-free reactions. Herein, we report the use of tBuOK for S-S, S-Se, NN and CN bond formations, which significantly extends the scope of tBuOK in chemical synthesis. Compared with traditional methods, we have realized mild and general methods for disulfide, azobenzenes imine etc. synthesis.
- Xu, Yulong,Shi, Xiaonan,Wu, Lipeng
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p. 24025 - 24029
(2019/08/13)
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- Natural gallic acid catalyzed aerobic oxidative coupling with the assistance of MnCO3 for synthesis of disulfanes in water
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The formation of S-S bonds has great significance and value in synthetic chemistry and bioscience. To pursue a sustainable approach for such a synthesis, an aerobic oxidative coupling method for the efficient preparation of organic disulfanes, using a low-toxic natural gallic acid as an organocatalyst, inexpensive MnCO3 as a cocatalyst, O2 as the terminal oxidant and water as the solvent, has been successfully developed. Such metal-organic cooperative catalytic protocol provided an access to various symmetrical and unsymmetrical disulfanes in up to 99% yield. Gram scale synthesis with practical convenience and low loading of catalysts further illustrates the practicability of our method.
- Song, Lijuan,Li, Wenhao,Duan, Wenxue,An, Jichao,Tang, Shanyu,Li, Longjia,Yang, Guanyu
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supporting information
p. 1432 - 1438
(2019/03/26)
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- Unsymmetrical Disulfide Synthesis through Photoredox Catalysis
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A facile and eco-friendly visible light-mediated synthesis of symmetrical and unsymmetrical disulfides using tris[2-phenylpyridinato-C2,N]iridium(III) under additive and oxidant free conditions has been disclosed. The developed method is very mild, several functional group tolerant and highly atom economical requiring extremely low amount of catalyst loading (0.5 mol%). (Figure presented.).
- Dethe, Dattatraya H.,Srivastava, Aparna,Dherange, Balu D.,Kumar, B. Vijay
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supporting information
p. 3020 - 3025
(2018/08/23)
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- Electro-Oxidative S?H/S?H Cross-Coupling with Hydrogen Evolution: Facile Access to Unsymmetrical Disulfides
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Sulfur is an essential element because it exists widely in proteins. The disulfide bond is an important moiety in many different types of significant organic molecules. A new approach for oxidant- and catalyst-free S?H/S?H cross-coupling, with hydrogen ev
- Huang, Pengfei,Wang, Pan,Tang, Shan,Fu, Zhuangjiong,Lei, Aiwen
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supporting information
p. 8115 - 8119
(2018/06/04)
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- Synthesis and in vitro biological evaluation of thiosulfinate derivatives for the treatment of human multidrug-resistant breast cancer
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Organosulfur compounds derived from Allium vegetables have long been recognized for various therapeutic effects, including anticancer activity. Allicin, one of the main biologically active components of garlic, shows promise as an anticancer agent; however, instability makes it unsuitable for clinical application. The aim of this study was to investigate the effect of stabilized allicin derivatives on human breast cancer cells in vitro. In this study, a total of 22 stabilized thiosulfinate derivatives were synthesized and screened for their in vitro antiproliferative activities against drug-sensitive (MCF-7) and multidrug-resistant (MCF-7/Dx) human adenocarcinoma breast cancer cells. Assays for cell death, apoptosis, cell cycle progression and mitochondrial bioenergetic function were performed. Seven compounds (4b, 7b, 8b, 13b, 14b, 15b and 18b) showed greater antiproliferative activity against MCF-7/Dx cells than allicin. These compounds were also selective towards multidrug-resistant (MDR) cells, a consequence attributed to collateral sensitivity. Among them, 13b exhibited the greatest anticancer activity in both MCF-7/Dx and MCF-7 cells, with IC50 values of 18.54±0.24 and 46.50±1.98 μmol/L, respectively. 13b altered cellular morphology and arrested the cell cycle at the G2/M phase. Additionally, 13b dose-dependently induced apoptosis, and inhibited cellular mitochondrial respiration in cells at rest and under stress. MDR presents a significant obstacle to the successful treatment of cancer clinically. These results demonstrate that thiosulfinate derivatives have potential as novel anticancer agents and may offer new therapeutic strategies for the treatment of chemoresistant cancers.
- Roseblade, Ariane,Ung, Alison,Bebawy, Mary
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p. 1353 - 1368
(2017/10/10)
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- Efficient one-pot construction of unsymmetrical disulfide bonds with TCCA
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We report herein a one-pot synthesis of unsymmetrical disulfides with trichloroisocyanuric acid (TCCA) as an oxidant. Under facile conditions, aromatic-aromatic disulfides and aromatic-aliphatic disulfides were synthesized in good to excellent yields even
- Yang, Feng,Wang, Wen,Li, Kaidi,Zhao, Weili,Dong, Xiaochun
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supporting information
p. 218 - 222
(2016/12/27)
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- Method for synthesizing asymmetric disulfide by using trichloroisocyanuric acid (TCCA)
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The invention relates to a method for synthesizing asymmetric disulfide, belonging to the field of chemical synthesis. The invention specifically relates to a method for synthesizing asymmetric disulfide by oxidizing different mercaptans or thiophenols wi
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Paragraph 0023
(2018/04/01)
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- A traceless, one-pot preparation of unsymmetric disulfides from symmetric disulfides through a repeated process involving sulfenic acid and thiosulfinate intermediates
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A variable group of unsymmetric disulfides was prepared under mild reaction conditions and in high yields through the reaction of symmetric disulfides with sulfuryl chloride followed by treatment with thiols in the presence of water.
- Han, Minsoo,Lee, Jong Tak,Hahn, Hoh-Gyu
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experimental part
p. 236 - 239
(2011/02/28)
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- Inexpensive, one-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole
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A new synthesis of unsymmetrical disulfides is described. The reaction of a thiol R1SH with 1-chlorobenzotriazole (BtCl) at -78 °C in DCM affords a high-yielding conversion to R1SBt without appreciable formation of the symmetrical disulfide R1SSR1. R1SBt is then reacted with R2SH to form the unsymmetrical disulfide in a one-pot sequence with green character that avoids the use of toxic and harsh oxidizing agents. The methodology has been developed for synthesis of various types of disulfides.
- Hunter, Roger,Caira, Mino,Stellenboom, Nashia
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p. 8268 - 8271
(2007/10/03)
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