- Carbohydrates as efficient catalysts for the hydration of α-amino nitriles
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Directed hydration of α-amino nitriles was achieved under mild conditions using simple carbohydrates as catalysts exploiting temporary intramolecularity. A broadly applicable procedure using both formaldehyde and NaOH as catalysts efficiently hydrated a variety of primary and secondary susbtrates, and allowed the hydration of enantiopure substrates to proceed without racemization. This work also provides a rare comparison of the catalytic activity of carbohydrates, and shows that the simple aldehydes at the basis of chemical evolution are efficient organocatalysts mimicking the function of hydratase enzymes. Optimal catalytic efficiency was observed with destabilized aldehydes, and with difficult substrates only simple carbohydrates such as formaldehyde and glycolaldehyde proved reliable.
- Chitale, Sampada,Derasp, Joshua S.,Hussain, Bashir,Tanveer, Kashif,Beauchemin, André M.
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supporting information
p. 13147 - 13150
(2016/11/09)
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- SUBSTITUTED (THIAZOLYL-CARBONYL)IMIDAZOLIDINONES AND USE THEREOF
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The present invention relates to novel substituted furancarboxamides, methods for their production, their use for the treatment and/or prevention of diseases, as well as their use for the production of medicaments for the treatment and/or prophylaxis of diseases, especially retroviral diseases, in humans and/or animals.
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Paragraph 0209; 0210; 0211; 0212
(2013/03/26)
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- SUBSTITUTED (THIOPHENYL-CARBONYL)IMIDAZOLIDINONES, AND USE THEREOF
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The present invention relates to novel substituted (thiophenyl-carbonyl)imidazolidinones, methods for their production, their use for the treatment and/or prevention of diseases, as well as their use for the production of medicaments for the treatment and/or prophylaxis of diseases, especially retroviral diseases, in humans and/or animals.
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Page/Page column 11
(2012/02/03)
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- SUBSTITUTED FURANCARBOXAMIDES, AND USE THEREOF
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The present invention relates to novel substituted furancarboxamides, methods for their production, their use for the treatment and/or prevention of diseases, as well as their use for the production of medicaments for the treatment and/or prophylaxis of diseases, especially retroviral diseases, in humans and/or animals.
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Page/Page column 18
(2012/02/03)
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- SUBSTITUTED (PYRAZOLYLCARBONYL)IMIDAZOLIDINONES AND THEIR USE
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The present invention relates to novel substituted (pyrazolylcarbonyl)imidazolidinones, methods for their preparation, their use for the treatment and/or prophylaxis of diseases, as well as their use for the manufacture of medicaments for the treatment and/or prophylaxis of diseases, especially of retroviral diseases, in humans and/or animals.
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Page/Page column 38
(2011/06/19)
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- Conformation of Nα-substituted hydrazino acetamides in CDCl3, the precious help of the analysis of Δδ between amidic hydrogens, and correlation to the conformation of aza-β3- peptides
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We studied the conformation of a series of primary amides in a solution of chloroform. Classical NMR tools such as dilution experiments, influence of DMSO, and 2D-NOESY, together with X-ray diffraction, were combined with an analysis of the difference of the chemical shift Δδ between the geminal amidic protons. This study was addressed in order to understand the conformation adopted by hydrazino acetamides 1a and 1b as model compounds for aza-β3-peptides. In this manner, it was possible to show that the amidic group of these compounds acts as a H-bond donor and interacts with two different H-bond acceptors. We concluded that the hydrazinoturn, a specific bifurcated H-bond system observed in the solid state, is also the preferred conformation of hydrazino acetamides 1a and 1b in solution. Our results show that the short-range interaction with the Nα-nitrogen lone pair not only stabilizes the C8 pseudocycle but could also contribute to the folding process of aza-β3-peptides. In light of this, it could explain why aza-β3-peptides develop a different H-bond network in comparison to their isosteric β3-peptides analogues. Our work is in keeping with the recent interest of hydrazino peptides as an extension of the β-peptide concept.
- Salauen, Arnaud,Favre, Annaick,Le Grel, Barbara,Potel, Michel,Le Grel, Philippe
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p. 150 - 158
(2007/10/03)
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