59830-61-4Relevant academic research and scientific papers
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.
Resolution and absolute configuration of some a-aminoacetals: En route to enantiopure N-protected a-aminoaldehydes
Albalat-Serradeil, Muriel,Primazot, Geraldine,Wilhelm, Didier,Vallejos, Jean-Claude,Vanthuyne, Nicolas,Roussel, Christian
, p. 687 - 696 (2012/09/22)
The first successful resolution of rac-a-aminoacetals via diastereoisomeric salt formation with optically pure N-protected aminoacids is reported. The absolute configuration assignment of a-aminoacetal enantiomers is performed by an entirely non-racemizing chemical correlation method involving N-protection and a new efficient hydrolysis step followed by a reduction of the resulting N-protected a-aminoaldehyde intermediates. A racemization method of optically enriched a-aminoacetals is exemplified to allow valorisation of both enantiomers. Springer-Verlag 2011.
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
PROCESS OF DEACETALISATION OF ALPHA AMINOACETALS
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Page/Page column 23-24, (2008/12/08)
The invention relates to a process for the preparation of N-protected α-aminoaldehydes by deacetalization of the acetal functional group of corresponding N-protected α-aminoacetals using formic acid.
Asymmetric Synthesis of 2- Amino Alcohol Derivatives from (S)-α-Amino Aldehydes via Acetal Templates
Kano, Shinzo,Yokomatsu, Tsutomu,Iwasawa, Haruo,Shibuya, Shiroshi
, p. 1531 - 1534 (2007/10/02)
Titanium tetrachloride mediated addition of allyltrimethylsilane to chiral acetals derived from (S)-α-amino aldehydes and (+)-(2S,4S)-pentane-2,4-diol gave the anti-2-amino alcohol derivatives with considerably high diastereoselectivity.On the other hand,
DIASTEREOSELECTIVE SYNTHESIS OF 2,3-CIS-2-ALKYL-3-OXYGENATED PIPERIDINE DERIVATIVES BY TITANIUM MEDIATED INTRAMOLECULAR CYCLIZATION OF α-AMINOACETAL-ALLYLSILANE SYSTEM
Kano, Shinzo,Yokomatsu, Tsutomu,Iwasawa, Haruo,Shibuya, Shiroshi
, p. 2805 - 2809 (2007/10/02)
(2S,3S)-2-Alkyl-3-oxygenated 5-methylenepiperidines were obtained with high diastereoselectivity by cyclization of N-methoxycarbonyl-N-silylmethallyl-α-alkylaminoacetaldehyde ethyleneacetals with TiCl3(OPri).
