16766-09-9Relevant academic research and scientific papers
Synthetic method of diaryl disulfide compound
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Paragraph 0046-0055, (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.
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.
Selective N-acetylation with concurrent S-oxidation of o-amino thiol at ambient conditions over Ce doped ZnO composite nanocrystallites
Jagtap, Rohidas,Sakate, Sachin,Pardeshi, Satish
, p. 19 - 28 (2018/04/27)
The oxidative S–S coupling of thiol to disulfide is an imperative chemical transformation in the domain of biological processes and also finds numerous chemical applications. The CeO2 and ZnO are significant catalysts for oxidation of thiol to disulfide and N-acetylation of amines respectively. Dithiobis(phenylene)bis(benzyldeneimine) moiety containing N-acetyl and disulfide functional groups is a potential antimicrobial agent with Leishmanicidal and antihyperlipidemic activities. Herein, we report a synchronized catalytic application of Ce doped ZnO (Ce-ZnO) and CeO2-Ce-ZnO composites for selective synthesis of Dithiobis(phenylene)bis(benzyldeneimine) from o-amino thiol. The Ce-ZnO samples were synthesized by simple co precipitation method by calcination of hydroxide precursors at 400 °C to get 0–10% Ce-ZnO nanocrystallites. The formation of CeO2-Ce-ZnO composite material was observed beyond 1.5% Ce concentration. The synthesized materials were well characterized by IR, XRD, DRS spectroscopy and SEM-EDS analysis. The application of Ce doped ZnO as an efficient catalyst towards the selective N-acetylation and concurrent S-oxidation of o-amino thiol to afford Dithiobis(phenylene)bis(benzyldeneimine) at ambient temperature in acetonitrile was deliberated. Among all screened catalysts, the maximum selectivity was found for 7.5% Ce-ZnO as CeO2-Ce-ZnO composite catalyst. Lewis acidic property of catalyst supported probable mechanism for achieved dual transformations. Also, the 7.5% Ce-ZnO catalyst has demonstrated a versatile S–S coupling ability for variety of thiol substrates with excellent stability.
Stereoretentive C(sp3)-S Cross-Coupling
Zhu, Feng,Miller, Eric,Zhang, Shuo-Qing,Yi, Duk,O'Neill, Sloane,Hong, Xin,Walczak, Maciej A.
supporting information, p. 18140 - 18150 (2019/01/04)
We report a stereoretentive cross-coupling reaction of configurationally stable nucleophiles with disulfide and N-sulfenylsuccinimide donors promoted by Cu(I). We demonstrate the utility of this method in the synthesis of thioglycosides derived from simple alkyl and aryl thiols, thioglycosides, and in the glycodiversification of cysteine residues in peptides. These reactions operate well with carbohydrate substrates containing common protective groups and reagents with free hydroxyl and secondary amide functionalities under standardized conditions. Competition experiments in combination with computational DFT studies established that the putative anomeric intermediate is an organocopper species that is configurationally stable and resistant to epimerization due to its short lifetime. The subsequent reductive elimination from the Cu(III) intermediate is rapid and stereoretentive. Taken together, the glycosyl cross-coupling is ideally suited for late stage glycodiversification and bioconjugation under highly controlled installation of the aliphatic carbon-sulfur bonds.
PEGylation of the peptide Bac7(1-35) reduces renal clearance while retaining antibacterial activity and bacterial cell penetration capacity
Benincasa, Monica,Zahariev, Sotir,Pelillo, Chiara,Milan, Annalisa,Gennaro, Renato,Scocchi, Marco
supporting information, p. 210 - 219 (2015/03/31)
The proline-rich antibacterial peptide Bac7(1-35) protects mice against Salmonella typhimurium infection, despite its rapid clearance. To overcome this problem the peptide was linked to a polyethylene glycol (PEG) molecule either via a cleavable ester bond or via a non-hydrolysable amide bond. Both the PEGylated conjugates retained most of the in vitro activity against S. typhimurium. In addition, the ester bond was cleaved in human serum or plasma, releasing a carboxymethyl derivative of Bac7(1-35) which accounts for a higher activity of this peptide with relative to the other, non-hydrolysable form. Both PEGylated peptides maintained the capacity of the unconjugated form to kill bacteria without permeabilizing the bacterial membranes, by penetrating into cells. They exploited the same transporter as unmodified Bac7(1-35), suggesting it has the capacity to internalize quite sizeable cargo if this is linked to Bac7 fragment. PEGylation allows the peptide to have a wide distribution in mice, and a slow renal clearance, indicating that this strategy would improve the bioavailability of Bac7, and in principle of other antimicrobial peptides. This can be an equally important issue to reducing cytotoxicity for therapeutic use of these antibacterials.
Synthesis of diaryl disulfides via mild reduction of arylsulfinates with hydrazine monohydrate in DMSO
Zhu, Rui-Heng,Shi, Xiao-Xin
experimental part, p. 1108 - 1114 (2012/04/04)
Arylsulfinates were reduced with hydrazine monohydrate at room temperature in dimethylsulfoxide (DMSO) to afford diaryl disulfides in good yields. A dramatic solvent effect was observed, and DMSO was found to be the best solvent for the reaction. Copyright Taylor & Francis Group, LLC.
An improved method for the synthesis of disulfides by periodic acid and sodium hydrogen sulfite in water
Khan, Khalid M.,Taha, Muhammad,Rahim, Fazal,Ali, Muhammad,Jamil, Waqas,Perveen, Shahnaz,Iqbal Choudhary
experimental part, p. 415 - 419 (2011/03/22)
An improved method for the synthesis of disulfide in water by using periodic acid and sodium hydrogen sulfite was developed.
The autoxidation of triaryl trithioarsenites, (ArS)3As: Evidence for binding and activation of triplet dioxygen by arsenic(III)
Haikou, Maria N.,Ioannou, Panayiotis V.
, p. 363 - 376 (2007/10/03)
Triaryl trithioarsenites, (ArS)3As, are oxidized by air to As2O3 and ArSSAr. In two cases the parent "thiol" (pyrid-2-thione and 1-hydroxypyrid-2-thione) is coproduced. The oxidation, in nonprotic solvents, is favored by electron-withdrawing groups at the para position of the phenyl group. The products obtained in nonprotic solvents were rationalized by assuming that the binding of the triplet dioxygen to arsenic(III) gives a triplet diradical, (ArS)3As-O-O, or an arsenadioxirane, (ArS)3As(O2), intermediate, which decomposes after nucleophilic attack by another (ArS)3As molecule. In protic solvents a zwitterion, (ArS)3As+-O-O-, and in the presence of moisture a hydroperoxy arsenic(V) compound, (ArS) 3As(OH)-O-OH, may be intermediates in the air oxidation of some aromatic trithioarsenites. These data tend to indicate that arsenic(III) bound to suitable groups can directly bind dioxygen, a property which may have implications in chemotherapy and carcinogenesis. Copyright Taylor & Francis Group, LLC.
Synthesis and Photochemistry of a New Class of Photocleavable Protein Cross-linking Reagents
Milanesi, Lilia,Reid, Gavin D.,Beddard, Godfrey S.,Hunter, Christopher A.,Waltho, Jonathan P.
, p. 1705 - 1710 (2007/10/03)
A new series of photocleavable protein cross-linking reagents based on bis(maleimide) derivatives of diaryl disulfides have been synthesised. They have been functionalised with cysteine and transient absorption spectra for the photolysis reaction have been recorded by using the pump-probe technique with a time resolution of 100 femtoseconds. Photolysis of the disulfide bond yields the corresponding thiyl radicals in less than a picosecond. There is a significant amount of geminate recombination, but some of the radicals escape the solvent cage and the quantum yield for photocleavage is 30% in water.
Electronic properties of para-substituted thiophonols and disulfides from 13C NMR spectroscopy and ab initio calculations: Relations to the Hammett parameters and atomic charges
Sengar, Raghvendra S.,Nemykin, Victor N.,Basu, Partha
, p. 1115 - 1123 (2007/10/03)
A large number of para-substituted benzene thiols and the corresponding disulfides were synthesized and characterized by 1H NMR, 13C NMR, and IR spectroscopies. Geometrics of all sixteen thiols and fourteen disulfide compounds were optimized at the B3LYP/6-31G(d) level, while the electronic structure and the 13C isotropic shifts were calculated by ab initio Hartree-Fock method coupled with the Gauge-Independent Atomic Orbital (GIAO) algorithm and a 6-31+G(d,p) basis set. The calculated 13C NMR isotropic shifts exhibit admirable agreement (δ rmsd ～4.6 ppm) with the experimental data. The chemical shift of para-substituted carbon showed a linear correlation with Hammett constants (σp and σn+). Using this methodology the σp+ constants for the dendritic ligands have been estimated to be 0.25 and 0.24 for 2(n) and 2(o), respectively. In addition, the NBO charges on the sulfur atoms shows a latent response with the σp+ parameter. The atomic charge on the thiophenolato sulfur is invariant with the electron withdrawing ability of the substituents, however, the charge increases with increasing electron-withdrawing power.
