14173-25-2Relevant academic research and scientific papers
Synthesis of 2-Thio-Substituted 1,6-Diazabicyclo[3.2.1]octane Derivatives, Potent β-Lactamase Inhibitors
Aoki, Toshiaki,Fujiu, Motohiro,Komano, Kazuo,Kusano, Hiroki,Ogawa, Masayoshi,Sato, Jun,Sato, Soichiro,Shibuya, Satoru,Yamawaki, Kenji,Yokoo, Katsuki
, p. 9650 - 9660 (2020)
Approval of avibactam by the FDA has led to the recognition of 1,6-diazabicyclo[3.2.1]octane (DBO) derivatives as attractive compounds for β-lactamase inhibition. We achieved a concise and collective synthesis of 2-thio-substituted DBO derivatives. The synthesis involves diastereoselective photo-induced Barton decarboxylative thiolation, which can be applied to large-scale synthesis. The DBO analogues exhibited strong inhibitory activities against serine β-lactamases and acceptable solution stabilities for clinical development.
Bioactive pyridine-N-oxide disulfides from allium stipitatum
O'Donnell, Gemma,Poeschl, Rosemarie,Zimhony, Oren,Gunaratnam, Mekala,Moreira, Joao B. C.,Neidle, Stephen,Evangelopoulos, Dimitrios,Bhakta, Sanjib,Malkinson, John P.,Boshoff, Helena I.,Lenaerts, Anne,Gibbons, Simon
, p. 360 - 365 (2009)
From Allium stipitatum, three pyridine-N-oxide alkaloids (1-3) possessing disulfide functional groups were isolated. The structures of these natural products were elucidated by spectroscopic means as 2-(methyldithio)pyridine-N- oxide (1), 2-[(methylthiome
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
On the thermal Pummerer rearrangement of substituted sulfoxides
Marzorati, Liliana,Yoshikawa, Eduardo K.C.,Braga, Ataualpa A.C.,Di Vitta, Claudio
, p. 248 - 260 (2014/04/03)
Sulfoxides bearing thioester and ester groups at the position under heating at ca. 140C undergo Pummerer thermal rearrangement. However, for sulfonyl sulfoxide, a complex mixture of products is formed. Plausible mechanism is advanced(equation presented. 2013
Enzyme-catalysed oxidation of 1,2-disulfides to yield chiral thiosulfinate, sulfoxide and cis-dihydrodiol metabolites
Boyd, Derek R.,Sharma, Narain D.,Shepherd, Steven D.,Allenmark, Stig G.,Allen, Christopher C. R.
, p. 27607 - 27619 (2014/07/21)
Enantioenriched and enantiopure thiosulfinates were obtained by asymmetric sulfoxidation of cyclic 1,2-disulfides, using chemical and enzymatic (peroxidase, monooxygenase, dioxygenase) oxidation methods and chiral stationary phase HPLC resolution of racemic thiosulfinates. Enantiomeric excess values, absolute configurations and configurational stabilities of chiral thiosulfinates were determined. Methyl phenyl sulfoxide, benzo[c]thiophene cis-4,5-dihydrodiol and 1,3-dihydrobenzo[c]thiophene derivatives were among unexpected types of metabolites isolated, when acyclic and cyclic 1,2-disulfide were used as substrates for Pseudomonas putida strains. Possible biosynthetic pathways are presented for the production of metabolites from 1,4-dihydrobenzo-2,3-dithiane, including a novel cis-dihydrodiol metabolite that was also derived from benzo[c]thiophene and 1,3-dihydrobenzo[c]thiophene.
On aromatic electrophilic substitution promoted by in situ generated thionium ions
Amici, Rosanaribeiro,Di Vitta, Claudio,Marzorati, Liliana
, p. 798 - 802 (2013/04/23)
α-Sulfanylated α-arylacetates and -thioacetates were prepared via ethylthiomethylation reaction of aromatic compounds. These aromatic electrophilic substitutions were performed by in situ generation of the thionium ions by reacting trifluoroacetic anhydri
Phosphine-catalyzed disulfide metathesis
Caraballo, Remi,Rahm, Martin,Vongvilai, Pornrapee,Brinck, Tore,Ramstroem, Olof
scheme or table, p. 6603 - 6605 (2009/04/20)
The reaction between disulfides and phosphines generates a reversible disulfide metathesis process. The Royal Society of Chemistry 2008.
Sulfur containing compounds
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Page/Page column 25, (2010/11/30)
This invention is directed to novel and known stufur containing compounds and pharmaceutically acceptable salts thereof that have utility as antifungals and as antiproliferative agents against mammalian cells, in particular cancer cells and most particularly leukemia-derived cells. The invention provides a method for synthesizing certain of the sulfur containing compounds that is more efficient than previously known methods.
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.
Cleavage of S-S bond by nitric oxide (NO) in the presence of oxygen: A disproportionation reaction of two disulfides
Tsutsumi,Itoh,Ohsawa
, p. 1524 - 1528 (2007/10/03)
Disulfide bond was cleaved by a catalytic amount of nitric oxide in the presence of oxygen, which was confirmed by experiments employing two symmetrical disulfides. The reaction resulted in the formation of unsymmetrical disulfides in nearly 50% yields. The steric hindrance of alkyl disulfide slowed the reaction rate, and an electron-donating group on the aryl disulfide promoted the reaction. The substituent and S-nitrosothiol effects suggested that the reaction was initialized with an oxidative process by NO+.
