Browsing by Subject "RING"

Sort by: Order: Results:

Now showing items 1-3 of 3
  • Luecke, Ana-Luiza; Wiechmann, Sascha; Freese, Tyll; Nieger, Martin; Foeldes, Tamas; Papai, Imre; Gjikaj, Mimoza; Adam, Arnold; Schmidt, Andreas (2018)
    Unstable N-heterocyclic carbenes can be masked and stabilized as pseudo-cross-conjugated hetarenium-carboxylates which decarboxylate on warming. This study deals with the decarboxylation of carboxylates of mesoionic compounds to generate anionic N-heterocyclic carbenes. Lithium sydnone-4-carboxylates were therefore prepared via 4-bromosydnones by halogen-lithium exchange with nBuLi and subsequent treatment with carbon dioxide. Protonation gave the corresponding sydnone-4-carboxylic acids. Thermogravimetric measurements in addition to temperature dependent IR spectroscopy proved the decarboxylation of lithium sydnone-4-carboxylates and formation of the corresponding sydnone anions which can be represented as anionic N-heterocyclic carbenes. In DMSO-d6 solution, water favors the decarboxylation. Calculations have been performed to elucidate the mechanism of the decarboxylation in the absence and presence of water. (C) 2018 Elsevier Ltd. All rights reserved.
  • Cruz, Cristina D; Wrigstedt, Pauli; Moslova, Karina; Iashin, Vladimir; Mäkkylä, Heidi; Ghemtio, Leo; Heikkinen, Sami; Tammela, Päivi; Perea-Buceta, Jesus Enrique (2021)
    N-aryl-oxazolidinones is a prominent family of antimicrobials used for treating infections caused by clinically prevalent Gram-positive bacteria. Recently, boron-containing compounds have displayed intriguing potential in the antibiotic discovery setting. Herein, we report the unprecedented introduction of a boron-containing moiety such as an aryl boronic acid in the external region of the oxazolidinone structure via a chemoselective acyl coupling reaction. As a result, we accessed a series of analogues with a distal aryl boronic pharmacophore on the oxazolidinone scaffold. We identified that a peripheric linear conformation coupled with freedom of rotation and no further substitution on the external aryl boronic ring, an amido linkage with hydrogen bonding character, in addition to a para-relative disposition between boronic group and linker, are the optimal combination of structural features in this series for antimicrobial activity. In comparison to linezolid, the analogue comprising all those features, compound 20b, displayed levels of antimicrobial activity augmented by an eight-fold to a thirty-two-fold against a panel of Gram-positive strains, and a near one hundred-fold against Escherichia coli JW5503, a Gram-negative mutant strain with a defective efflux capability.
  • Turner, D. L.; Kilpua, E. K. J.; Hietala, H.; Claudepierre, S. G.; O'Brien, T. P.; Fennell, J. F.; Blake, J. B.; Jaynes, A. N.; Kanekal, S.; Baker, D. N.; Spence, H. E.; Ripoll, J.-F.; Reeves, G. D. (2019)
    A statistical study was conducted of Earth's radiation belt electron response to geomagnetic storms using NASA's Van Allen Probes mission. Data for electrons with energies ranging from 30 keV to 6.3 MeV were included and examined as a function of L-shell, energy, and epoch time during 110 storms with SYM-H 1 MeV also revealed a marked increase in likelihood of a depletion at all L-shells through the outer belt (3.5 1-MeV electrons throughout the outer belt, while storms driven by full CMEs and stream interaction regions are most likely to produce an enhancement of MeV electrons at lower (L <similar to 5) and higher (L > similar to 4.5) L-shells, respectively. CME sheaths intriguingly result in a distinct enhancement of similar to 1-MeV electrons around L similar to 5.5, and on average, CME sheaths and stream interaction regions result in double outer belt structures.