16066-31-2Relevant academic research and scientific papers
2-AMINO-N-(AMINO-OXO-ARYL-LAMBDA6-SULFANYLIDENE)ACETAMIDE COMPOUNDS AND THEIR THERAPEUTIC USE
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, (2021/06/26)
The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain 2-amino-N-(amino-oxo-aryl-λ6- sulfanylidene)acetamide compounds (referred to herein as ANASIA compounds) that, inter alia, inhibit (e.g., selectively inhibit) bacterial aminoacyl-tRNA synthetase (aaRS) (e.g., bacterial leucyl-tRNA synthetase, LeuRS). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit (e.g., selectively inhibit) bacterial aminoacyl-tRNA synthetase; to treat disorders that are ameliorated by the inhibition (e.g., selective inhibition) of bacterial aminoacyl-tRNA synthetase; to treat bacterial infections; etc.
Hydroxylamine-Derived Reagent as a Dual Oxidant and Amino Group Donor for the Iron-Catalyzed Preparation of Unprotected Sulfinamides from Thiols
Chatterjee, Sayanti,Makai, Szabolcs,Morandi, Bill
supporting information, p. 758 - 765 (2020/11/30)
An iron catalyzed reaction for the selective transformation of thiols (-SH) to sulfinamides (-SONH2) by a direct transfer of -O and free -NH2 groups has been developed. The reaction operates under mild conditions using a bench stable hydroxylamine derived reagent, exhibits broad functional group tolerance, is scalable and proceeds without the use of any precious metal catalyst or additional oxidant. This novel, practical reaction leads to the formation of two distinct new bonds (S=O and S?N) in a single step to chemoselectively form valuable, unprotected sulfinamide products. Preliminary mechanistic studies implicate the role of the alcoholic solvent as an oxygen atom donor.
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.
Using sulfinamides as high oxidation state sulfur reagent for preparation of sulfenamides
Ma, Long-jun,Li, Guang-xun,Huang, Jin,Zhu, Jin,Tang, Zhuo
supporting information, p. 1600 - 1603 (2018/03/28)
Traditional preparation of sulfenamides require the use of low oxidation state of sulfur reagent such as RSCl, (RS)2 or RSH, which are toxic, odorous and difficult to deal with due to the harsh reaction conditions. Here high oxidation state of
Synthesis of asymmetrical thioethers with sulfinamides as the sulfenylation agent under metal-free conditions
Ma, Long-jun,Li, Guang-xun,Huang, Jin,Zhu, Jin,Tang, Zhuo
supporting information, p. 4255 - 4258 (2018/10/31)
Using sulfinamides as a new reagent for preparation of asymmetrical thioethers has been developed under metal-free conditions. The reactions proceeded smoothly without the use of stinky thiophenol, highly toxic sulfonyl chloride or oxidant. Such a simple, efficient transformation provides an attractive approach to various diaryl sulfides in good to excellent yields.
Fe(III)/ l -Valine-Catalyzed One-Pot Synthesis of N -Sulfinyl- and N -Sulfonylimines via Oxidative Cascade Reaction of Alcohols with Sulfinamides or Sulfonamides
Zhang, Guofu,Xing, Yunzhe,Xu, Shengjun,Ding, Chengrong,Shan, Shang
supporting information, p. 1232 - 1238 (2018/03/23)
An efficient Fe(III), l -valine, and 4-OH-TEMPO catalytic system was found for the oxidation of alcohols followed by condensation with sulfinamide or sulfonamide in one pot for the synthesis of N -sulfinyl- and N- sulfonylimines compounds under mild conditions. This transformation accommodates a variety of substrates, shows high functional-group tolerance, and affords the corresponding products in good to excellent yields.
2-AMINO-N-(ARYLSULFINYL)-ACETAMIDE COMPOUNDS AS INHIBITORS OF BACTERIAL AMINOACYL-TRNA SYNTHETASE
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Page/Page column 75; 92-93, (2018/04/21)
The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain 2-amino-N-(arylsulfinyl)- acetamide compounds that, inter alia, inhibit (e.g., selectively inhibit) bacterial amino
PLATELET ADP RECEPTOR INHIBITORS
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Paragraph 0078, (2016/08/17)
no abstract published
Synthesis and arylation of unprotected sulfonimidamides
Funes Maldonado, Matías,Sehgelmeble, Fernando,Bjarnemark, Fanny,Svensson, Mats,?hman, Jens,Arvidsson, Per I.
experimental part, 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,
Activated sterically strained C=N bond in N-substituted p-quinone mono- and diimines: XIII. reactions of N-alkyl(aryl, trifl uoromethyl)sulfonyl-, N-arylsulfi nyl-and N-arylsulfanyl-1,4-benzoquinone monoimines with alcohols
Avdeenko,Konovalova,Mikhailichenko,Santalova,Palamarchuk,Shishkin
scheme or table, p. 642 - 650 (2012/10/08)
Steric strains arising between the substituent atoms at nitrogen (S, SO, or SO2) and the methyl group located in positions 3 or 5 of the quinoid ring of 3,5-dimethyl-substituted quinone monoimines lead to the increased angle C=N-S. As a result in these quinone monoimines the reactions of 1,2-addition become thermodynamically possible since the formation of quinolide structures with the sp3-hybridized carbon atom removes the steric strain.
