70975-34-7Relevant academic research and scientific papers
N -Trifluoromethylthiolated Sulfoximines
Bohnen, Christian,Bolm, Carsten
, p. 3011 - 3013 (2015)
Air- and moisture-stable N-trifluoromethylthio sulfoximines have been prepared from N-H-sulfoximines via the corresponding N-Br derivatives in excellent yields. The two-step process starts with an easy-to-perform bromination at the sulfoximine nitrogen, followed by a reaction with silver trifluoromethanethiolate. A one-pot reaction sequence allows difficult to prepare products to be obtained.
N-Trifluoromethylthiolated Sulfonimidamides and Sulfoximines: Anti-microbial, Anti-mycobacterial, and Cytotoxic Activity
Thota, Niranjan,Makam, Parameshwar,Rajbongshi, Kamal K.,Nagiah, Savania,Abdul, Naeem Sheik,Chuturgoon, Anil A,Kaushik, Amit,Lamichhane, Gyanu,Somboro, Anou M.,Kruger, Hendrik G.,Govender, Thavendran,Naicker, Tricia,Arvidsson, Per I
supporting information, p. 1457 - 1461 (2019/10/11)
Herein we demonstrate the expanded utility of a recently described N-trifluoromethylthiolation protocol to sulfonimidamide containing substances. The novel N-trifluoromethylthio sulfonimidamide derivatives thus obtained were evaluated for antibacterial activity against Mycobacterium tuberculosis (M. tb.) and Mycobacterium abscessus and Gram + Ve (Streptococcus aureus, Bacillus subtilis), and Gram - Ve (Escherichia coli, Pseudomonas aeruginosa) bacteria. Two compounds, 13 and 15 showed high antimycobacterial activity with MIC value of 4-8 μg/mL; i.e. comparable to WHO recommended first line antibiotic for TB infection ethambutol. The same compounds were also found to be cytotoxic in HepG2 cells (compound 13 IC50 = 15 μg/mL; compound 15 IC50 = 65 μg/mL). A structure activity relationship, using matched pair analysis, gave the unexpected conclusion that the trifluoromethylthio moiety was responsible for the cellular and bacterial toxicity. Given the increasing use of the trifluoromethylthio group in contemporary medicinal chemistry, this observation calls for considerations before implementation of the functionality in drug design.
Homolytic Reaction of N-Halogenosulphoximides with Olefins and Toluene
Akasaka, Takeshi,Furukawa, Naomichi,Oae, Shigeru
, p. 1257 - 1261 (2007/10/02)
Homolytic addition reaction of N-halogenosulphoximides, i.e. diphenyl-N-chlorosulphoximide (1), diphenyl-N-bromosulphoximide (2), and methylphenyl-N-chlorosulphoximide (3), to olefins such as t-butylethylene and cyclohexene under both u.v. irradiation and thermolysis in the presence of a radical initiator was found to afford the corresponding N-alkylated sulphoximides, which are presumed to be formed via the initial addition of the sulphoximidoyl radical.Meanwhile, homolytic bromination of toluene with N-bromosulphoximide (2) proceeded readily by u.v. irradiation, or by thermal reaction in the presence of a radical initiator, to afford benzyl bromide.However, chlorination of toluene was sluggish with N-chlorosulphoximides (1) and (3). α-Bromination was interpreted in terms of a chain process involving bromine molecules like the 'Goldfinger mechanism', but not via that involving the sulphoximidoyl radical.
