1394013-23-0Relevant academic research and scientific papers
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
, 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.
Sulfoximine-based modular enantioselective synthesis of azaspirocycles featuring sulfoximine displacement, dianion cycloalkylation, RCM and N-acyliminium ion formation
Koehler, Adeline,Raabe, Gerhard,Runsink, Jan,Koehler, Franz,Gais, Hans-Joachim
, p. 3355 - 3371 (2014/06/09)
We describe a modular, enantioselective synthesis of functionalised azaspirocycles with a range of ring sizes. The synthesis exploits the special features of sulfoximines, including chirality, carbanion-stabilisation, nucleophilicity, and nucleofugacity.
Synthesis and arylation of unprotected sulfonimidamides
Funes Maldonado, Matías,Sehgelmeble, Fernando,Bjarnemark, Fanny,Svensson, Mats,?hman, Jens,Arvidsson, Per I.
, p. 7456 - 7462 (2012/09/22)
Herein we evaluate different methodologies for the synthesis of unprotected sulfonimidamides. Three different procedures that allow orthogonal deprotection of the imine nitrogen under acidic, nucleophilic, and basic conditions were established. Moreover,
