63296-21-9Relevant academic research and scientific papers
NFSI-catalyzed S[sbnd]S bond exchange reaction for the synthesis of unsymmetrical disulfides
Hu, Qingyue,Li, Zheng-Yi,Song, Mengjie,Sun, Xiaoqiang,Yang, Ke
supporting information, (2022/01/26)
The metal-free S[sbnd]S bond exchange reaction of symmetrical disulfides catalyzed by NFSI is described. This novel protocol provides a facile and efficient approach to accessing important unsymmetrical disulfides. Furthermore, this strategy could also be utilized in the late-stage functionalization of amino acids, drugs, and natural products. The broad substrate scope, good functional group tolerance and easy accessibility of catalyst indicate that this strategy affords a green and practical complementary method to various unsymmetrical disulfides.
Convenient Unsymmetrical Disulfane Synthesis: Basic Zeolite-Catalyzed Thiol-Disulfane Exchange Reaction
Yamamoto, Eiji,Kawai, Yasutaka,Takakura, Kei,Kimura, Moemi,Murayama, Haruno,Matsueda, Hironobu,Otsuki, Shujiro,Sakata, Hiroshi,Tokunaga, Makoto
, p. 4694 - 4699 (2021/10/14)
Convenient catalytic synthetic methods for the preparation of unsymmetrical disulfanes are described. Na-exchanged X type zeolite (Na-X), commercially available as MS-13X, effectively catalyzes thiol-disulfane exchange reactions with 1.0 equivalent of thi
Unsymmetric aryl-alkyl disulfide growth inhibitors of methicillin-resistant Staphylococcus aureus and Bacillus anthracis
Turos, Edward,Revell, Kevin D.,Ramaraju, Praveen,Gergeres, Danielle A.,Greenhalgh, Kerriann,Young, Ashley,Sathyanarayan, Nalini,Dickey, Sonja,Lim, Daniel,Alhamadsheh, Mamoun M.,Reynolds, Kevin
, p. 6501 - 6508 (2008/12/21)
This study describes the antibacterial properties of synthetically produced mixed aryl-alkyl disulfide compounds as a means to control the growth of Staphylococcus aureus and Bacillus anthracis. Some of these compounds exerted strong in vitro bioactivity. Our results indicate that among the 12 different aryl substituents examined, nitrophenyl derivatives provide the strongest antibiotic activities. This may be the result of electronic activation of the arylthio moiety as a leaving group for nucleophilic attack on the disulfide bond. Small alkyl residues on the other sulfur provide the best activity as well, which for different bacteria appears to be somewhat dependent on the nature of the alkyl moiety. The mechanism of action of these lipophilic disulfides is likely similar to that of previously reported N-thiolated β-lactams, which have been shown to produce alkyl-CoA disulfides through a thiol-disulfide exchange within the cytoplasm, ultimately inhibiting type II fatty acid synthesis. However, the mixed alkyl-CoA disulfides themselves show no antibacterial activity, presumably due to the inability of the highly polar compounds to cross the bacterial cell membrane. These structurally simple disulfides have been found to inhibit β-ketoacyl-acyl carrier protein synthase III, or FabH, a key enzyme in type II fatty acid biosynthesis, and thus may serve as new leads to the development of effective antibacterials for MRSA and anthrax infections.
N-alkylthio beta-lactams, alkyl-coenzyme a asymmetric disulfides, and aryl-alkyl disulfides as anti-bacterial agents
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Page/Page column 12, (2008/12/07)
The present invention provides N-alkylthio β-lactams and disulfide compounds (e.g., alkyl-coenzyme A asymmetric disulfides or aryl-alkyl disulfides), compositions containing such compounds, and method of their use as anti-bacterial agents.
New and more potent antifungal bisulfides
Baerlocher, Felix Jakob,Baerlocher, Mark Otto,Langler, Richard Francis,MacQuarrie, Stephanie Lee,Marchand, Maurice Emile
, p. 1 - 5 (2007/10/03)
From a design principle described in an earlier paper, a new series of substituted aryl methyl disulfides have been prepared and tested against Aspergillus niger and Aspergillus flavus. Methyl p-nitrophenyl disulfide is more potent (by an order of magnitude) than the fungitoxic natural product (CH3SCH2S)2. With the present rationale in hand, one can anticipate which Polycarpamine is an effective antifungal agent. CSIRO 2000.
Formation of Stable Aryldisulphide Ions in Dimethylacetamide from the Reaction of Sulphur with Thiolate Ions
Benaichouche, Meriem,Bosser, Gerard,Paris, Jacky,Auger, Jacques,Plichon, Vincent
, p. 31 - 36 (2007/10/02)
The conditions for the formation of aryldisulphide ions, RS2- during the direct reaction of sulphur with thiolate ions RS- have been studied by the use of spectroelectrochemistry in dimethylacetamide.The series of derivatives examined was R = p-tolyl (1), phenyl (2), 8-quinolyl (3), 2- and 4-pyridyl (4), (5), N-oxido 4-pyridyl (6), 2- and 4-nitrophenyl (7), (8), and 2-(5-nitropyridyl) (9).Sulphur reaction leads to RS2- ions and preceded the oxidation to diaryldisulphide RS2R and polysulphide ions Sx-.With derivatives (1)-(3), both reactions are successive and practically stoicheiometric, while for derivatives containing electron-withdrawing groups (6)-(9), the equilibrium constants have been measured.Analysis of the reaction products by methylation of several solutions of thiolate ions in the presence of sulphur confirmed the possibility of obtaining aryldisulphide ions stabilized in aprotic dipolar media.
Stabilisation of Nitrophenyl Disulphide Ions in Dimethylacetamide
Bosser, Gerard,Paris, Jacky,Plichon, Vincent
, p. 720 - 721 (2007/10/02)
2-Nitrophenyl and 4-nitrophenyl disulphide ions are stabilised in aprotic dipolar solvents and solutions of these ions are obtained in dimethylacetamide by nucleophilic attack of sulphur by the corresponding thiolates.
