80466-51-9Relevant academic research and scientific papers
Cyclic Sulfamidite as Simultaneous Protecting Group for Amino Alcohols: Development of a Mild Deprotection Protocol Using Thiophenol
Sakata, Juri,Akita, Kazunari,Sato, Manabu,Shimomura, Masashi,Tokuyama, Hidetoshi
, p. 996 - 1000 (2020/11/03)
This study describes the novel utility of cyclic sulfamidite as a simultaneous protecting group for 1,2- or 1,3-amino alcohols. An exceptionally mild and neutral condition for the removal of the cyclic sulfamidite was developed. The deprotection condition demonstrated a broad range of functional-group compatibility, including a substrate bearing a Z-enyne structure without any loss of double-bond stereochemistry.
Zinc-Catalyzed Esterification of N-β-Hydroxyethylamides: Removal of Directing Groups under Mild Conditions
Nishii, Yuji,Hirai, Takahiro,Fernandez, Sarah,Knochel, Paul,Mashima, Kazushi
supporting information, p. 5010 - 5014 (2017/09/21)
Amide transformations involving C–N bond cleavage are recognized as difficult reactions owing to the inert nature of amides resulting from resonance. Accordingly, a strong inductive effect and geometrical distortion reasonably decrease the resonance stabilization to attenuate the C–N linkage. Although the conversion of such activated amides has been studied intensively, reaction systems for “unactivated” amides are underdeveloped. We herein report that a zinc(II) trifluoromethanesulfonate [Zn(OTf)2] catalyst achieves the esterification of a wide range of unactivated tertiary amides with the assistance of intramolecular acyl rearrangement. The reaction was applied to the one-pot removal of various amide-based directing groups under mild reaction conditions to afford the corresponding esters in high yields.
2-(2-Oxo-morpholin-3-yl)-acetamide derivatives as broad-spectrum antifungal agents
Bardiot, Dorothée,Thevissen, Karin,De Brucker, Katrijn,Peeters, Annelies,Cos, Paul,Taborda, Carlos P.,McNaughton, Michael,Maes, Louis,Chaltin, Patrick,Cammue, Bruno P. A.,Marchand, Arnaud
supporting information, p. 1502 - 1512 (2015/03/04)
From a fungicidal screen, we identified 2-(2-oxo-morpholin-3-yl)-acetamide derivatives as fungicidal agents against Candida species, additionally characterized by antifungal activity against Aspergillus species. However, development of this series was hampered by low plasmatic stability. Introduction of a gem-dimethyl on the 6-position of the morpholin-2-one core led to considerable improvement in plasmatic stability while maintaining in vitro antifungal activity. Further optimization of the series resulted in the discovery of N-(biphenyl-3-ylmethyl)-2-(4-ethyl-6,6-dimethyl-2-oxomorpholin-3-yl)acetamide (87), which, in addition to fungicidal activity against Candida species, shows promising and broad antifungal in vitro activity against various fungi species, such as molds and dermatophytes. In vivo efficacy was also demonstrated in a murine model of systemic Candida albicans infection with a significant fungal load reduction in kidneys.
ANTIFUNGAL COMPOUNDS
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Page/Page column 38, (2012/10/08)
The present invention relates to a series of novel compounds which have been shown to possess antifungal activity. The invention therefore relates to the new compounds, methods for their preparation, pharmaceutical compositions comprising them and to the compounds for use as a medicament, more in particular antifungal medicament.
ANTIFUNGAL COMPOUNDS
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Page/Page column 71, (2011/07/07)
The present invention relates to a series of novel compounds which have been shown to possess antifungal activity. The invention therefore relates to the new compounds, methods for their preparation, pharmaceutical compositions comprising them and to the compounds for use as a medicament, more in particular antifungal medicament.
