14173-25-2Relevant articles and documents
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.
Cragg et al.
, p. 1701 (1970)
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
