55707-43-2Relevant articles and documents
Modular construction of quaternary hemiaminal-based inhibitor candidates and their in cellulo assessment with HIV-1 protease
Gros, Guillaume,Martinez, Lorena,Gimenez, Anna Servat,Adler, Paula,Maurin, Philippe,Wolkowicz, Roland,Falson, Pierre,Hasserodt, Jens
supporting information, p. 5407 - 5413 (2013/09/02)
Non-peptidomimetic drug-like protease inhibitors have potential for circumventing drug resistance. We developed a much-improved synthetic route to our previously reported inhibitor candidate displaying an unusual quaternized hemi-aminal. This functional group forms from a linear precursor upon passage into physiological media. Seven variants were prepared and tested in cellulo with our HIV-1 fusion-protein technology that result in an eGFP-based fluorescent readout. Three candidates showed inhibition potency above 20 μM and toxicity at higher concentrations, making them attractive targets for further refinement. Importantly, our class of original inhibitor candidates is not recognized by two major multidrug resistance pumps, quite in contrast to most clinically applied HIV-1 protease inhibitors.
PROCESS FOR PREPARING ALPHA AMINOACETALS IN RECEMIC FORM
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Page/Page column 17-18, (2010/04/25)
The invention relates to a process for preparing an α-aminoacetal, or addition salts thereof, of formula (I) in recemic form comprising the steps consisting in: reacting a glyoxal monoacetal of formula (II) with an arylalkylamine of formula (III) in such a way as to obtain an imine of formula (IV); adding a Grignard reagent of formula R3-Mg-HaI to said imine of formula (IV) so as to obtain an amine of formula (V), and - deprotecting the amine of formula (V) in such a way as to obtain the compound of formula (I) in racemic form, and, where appropriate, adding an inorganic or organic acid in order to obtain an addition salt of the α-aminoacetal of formula (I).
Diversity-oriented synthesis of a drug-like system displaying the distinctive N→C=O interaction
Waibel, Michael,Hasserodt, Jens
, p. 6119 - 6126 (2008/12/22)
(Chemical Equation Presented) This study describes the syntheses and characterization of two hydrazino ureas. These fold into a six-membered ring by virtue of the infrequently observed δ+N→C=O δ- interaction when solvated by polar pr