71112-91-9Relevant academic research and scientific papers
Two polymorphs of bis(2-bromophenyl) disulfide
Anacona,Gomez, Jofre,Lorono, Daniel
, p. o277-o280 (2003)
Colourless crystals of the title compound, bis(2-bromophenyl) disulfide, C12H8Br2S2, are obtained from the reaction of 2-bromophenylmercaptan with metallic sodium and either zinc chloride or cadmium chloride in
Dual Roles of Rongalite: Reductive Coupling Reaction to Construct Thiosulfonates Using Sulfonyl Hydrazides
Zhang, Guofu,Fan, Qiankun,Zhao, Yiyong,Wang, Huimin,Ding, Chengrong
supporting information, p. 81 - 85 (2020/11/03)
A tunable and practical transformation of structurally diverse sulfonyl hydrazides into thiosulfonates in the presence of Rongalite (NaHSO 2·CH 2O) was developed. Transition-metal-free conditions, operational simplicity, and readily available reagents are the striking features of this protocol. It is the first example for the synthesis of thiosulfonates using sulfonyl hydrazides with the assistance of reductant. Additionally, the mechanistic studies revealed that this transformation probably undergoes via a reducing-coupling pathway.
Preparation method of symmetric disulfide bond-containing compound
-
Paragraph 0020; 0060-0062, (2021/11/21)
The method comprises the following steps: adding a raw material and an oxidant to a reaction bottle containing a solvent; reacting 23W - 85W under the irradiation of 12 - 24h energy-saving lamps; and purifying the reaction product to obtain symmetrical disulfide bond-containing compounds. The raw material is mercaptan or thiophenol. The oxidizing agent is trichlorobromomethane, and the solvent is tetrahydrofuran. The method has the advantages of simple operation, high yield (70 - 90%), wide applicability, cheap and easily available raw materials, and provides a better way for the synthesis and production of symmetrical disulfide bond-containing compounds.
Metal-free chalcogenation of cycloketone oxime esters with dichalcogenides
Ji, Liangshuo,Qiao, Jiamin,Liu, Junjie,Tian, Miaomiao,Lu, Kui,Zhao, Xia
supporting information, (2021/06/15)
We report the metal-free chalcogenation of cycloketone oxime esters with dichalcogenides via a radical process. Because of the metal-free condition and use of readily accessible dichalcogenides, this method is an effective and green strategy for the synthesis of chalcogen-substituted butyronitrile.
Sequential C-H activation enabled expedient delivery of polyfunctional arenes
Cai, Xiaoqing,Chen, Qian,Chen, Xiaojian,Gao, Yang,Huo, Yanping,Li, Xianwei,Ouyang, Wensen,Rao, Jianhang,Wang, Jie
supporting information, p. 8075 - 8078 (2021/08/20)
Modular construction of polyfunctional arenes from abundant feedstocks stands as an unremitting pursue in synthetic chemistry, accelerating the discovery of drugs and materials. Herein, using the multiple C-H activation strategy with versatile imidate esters, the expedient delivery of molecular libraries of densely functionalized sulfur-containing arenes was achieved, which enabled the concise construction of biologically active molecules, such as Bipenamol.
Diaryl disulfides and thiosulfonates as combretastatin A-4 analogues: Synthesis, cytotoxicity and antitubulin activity
Bai, Ruoli,Barbosa, Euzébio Guimar?es,Beatriz, Adilson,Hamel, Ernest,Khodyuk, Rejane Gon?alves Diniz,Louren?o, Estela Mariana Guimar?es,de Lima, Dênis Pires,dos Santos, Edson dos Anjos
, (2020/07/07)
Diaryl disulfides and diaryl thiosulfonates were synthesized with the two phenyl rings of all compounds bearing identical halide substituents. Because of structural similarity to the potent antimitotic natural product combretastatin A-4 (CA-4), the compounds were examined for inhibition of tubulin polymerization, and the thiosulfonates were more active than the disulfides. The nine thiosulfonates had IC50 values ranging from 1.2 to 9.1 μM, as compared with 1.3 μM obtained with CA-4. The compounds thus ranged from equipotent with CA-4 to 7-fold less active. The nine disulfides had IC50 values ranging from 1.2 to 5.1 μM, as compared with 0.54 μM obtained with CA-4. The compounds thus ranged from less than half as active as CA-4 to over 9-fold less active. The most active members of each group, 2 g and 3c, in the assembly assay were modeled into the colchicine site. Compound 3c had significant hydrophobic interactions with β-tubulin residues CYS 241 and ALA 250, and its thiosulfonate bridge made a hydrogen bond with β-tubulin residue ASN 258. Compound 2 g had hydrophobic interactions with β-tubulin residues ALA 250, CYS 241 and ALA 254, but there was no significant interaction of the disulfide bridge with tubulin.
Method for synthesizing symmetric disulfide compound by taking aryl hydrazine and S8 as raw materials
-
Paragraph 0064, (2020/11/23)
The invention relates to a method for synthesizing a symmetric disulfide compound by taking aryl hydrazine and S8 as raw materials, and belongs to the technical field of organic synthesis; the methodis characterized in that the aryl hydrazine compound and S8 are used as substrates to react in a reaction solvent under the promotion of alkali to generate the symmetric disulfide organic compound, the reaction gas atmosphere is air or oxygen, the reaction temperature is 40 DEG C-100 DEG C, and the reaction time is 4-24 hours. The synthesis steps are simple, the reaction conditions are mild, S8 which is widely distributed in nature, low in price and easy to obtain is used as a sulfur source, S-S bonds can be constructed only under the promotion of alkali without transition metal catalysis, theyield is as high as 95%, the applicable reaction substrate range is wide, the operation is simple and feasible, the synthesis cost is low, the environmental pollution is small, and a new thought is provided for the synthesis of the symmetric disulfide organic compound.
Natural gallic acid catalyzed aerobic oxidative coupling with the assistance of MnCO3 for synthesis of disulfanes in water
Song, Lijuan,Li, Wenhao,Duan, Wenxue,An, Jichao,Tang, Shanyu,Li, Longjia,Yang, Guanyu
supporting information, p. 1432 - 1438 (2019/03/26)
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.
Biocatalytic synthesis of diaryl disulphides and their bio-evaluation as potent inhibitors of drug-resistant Staphylococcus aureus
Saima,Soni, Isha,Lavekar, Aditya G.,Shukla, Manjulika,Equbal, Danish,Sinha, Arun K.,Chopra, Sidharth
, p. 171 - 178 (2019/01/04)
Staphylococcus aureus is a WHO Priority II pathogen for its capability to cause acute to chronic infections and to resist antibiotics, thus severely impacting healthcare systems worldwide. In this context, it is urgently desired to discover novel molecules to thwart the continuing emergence of antimicrobial resistance. Disulphide containing small molecules has gained prominence as antibacterials. As their conventional synthesis requires tedious synthetic procedure and sometimes toxic reagents, a green and environmentally benign protocol for their synthesis has been developed through which a series of molecules were obtained and evaluated for antibacterial activity against ESKAPE pathogen panel. The hit compound was tested for cytotoxicity against Vero cells to determine its selectivity index and time-kill kinetics was determined. The activity of hit was determined against a panel of S. aureus multi-drug resistant clinical isolates. Also, its ability to synergize with FDA approved drugs was tested as was its ability to reduce biofilm. We identified bis(2-bromophenyl) disulphide (2t) as possessing equipotent antimicrobial activity against S. aureus including MRSA and VRSA strains. Further, 2t exhibited a selectivity index of 25 with concentration-dependent bactericidal activity, synergized with all drugs tested and significantly reduced preformed biofilm. Taken together, 2t exhibits all properties to be positioned as novel scaffold for anti-staphylococcal therapy.
Visible-light-induced metal and reagent-free oxidative coupling of: Sp 2 C-H bonds with organo-dichalcogenides: Synthesis of 3-organochalcogenyl indoles
Rathore, Vandana,Kumar, Sangit
supporting information, p. 2670 - 2676 (2019/06/03)
Here, a unique visible-light-induced method for the organochalcogenation of the sp2 C-H bonds of indoles and aniline has been presented using diaryl dichalcogenides (S, Se, and Te) and oxygen as an oxidant avoiding a photocatalyst, base, catalyst, and reagent in acetone at room temperature. This benign protocol allows one to access a wide range of 3-arylselenylindoles, 3-arylthioindoles and even 3-aryltelluroindoles with good to excellent yields. Various functionalities namely, methoxy, and halo either on indoles or aryl dichalcogenides showed amenability to the developed reaction. Furthermore, thiocyanation of the sp2 C-H bonds of indoles has been accomplished by this visible light induced method. A mechanistic understanding by UV-visible, EPR spectroscopy, and cyclic voltammetry suggests that light induces electron transfer from the electron rich arene to oxygen providing an arene radical cation and a superoxide radical anion. Subsequently, reaction of the radical cation with aryl dichalcogenides provides a diaryl chalcogenyl cation which upon removal of protons gave unsymmetrical 3-indolyl aryl chalcogenides.
