- Disulfide metathesisviasulfur?iodine interaction and photoswitchability
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The idea of constitutional dynamic chemistry (CDC) and dynamic combinatorial chemistry (DCC) is widespread in the literature using the chemistry of disulfides. The synthesis of unsymmetrical diaryl disulfides is challenging due to the presence of a weak S
- Mal, Prasenjit,Mathuri, Ashis,Parida, Amarchand,Pramanik, Milan
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supporting information
p. 8539 - 8543
(2021/10/20)
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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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- Unsymmetrical Disulfides Synthesis via Sulfenium Ion
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An umpolung approach for the synthesis of unsymmetrical disulfides via sulfenium ion is reported. In situ generated electrophilic sulfenium ion from electron-rich thiols reacted with second thiols to yield unsymmetrical disulfides. Using an iodine catalyst and 4-dimethylaminopyridine (DMAP)/water as promoter, the target syntheses were achieved in one pot under aerobic condition.
- Parida, Amarchand,Choudhuri, Khokan,Mal, Prasenjit
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supporting information
p. 2579 - 2583
(2019/07/15)
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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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- 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 0014
(2018/04/01)
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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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