861889-26-1Relevant academic research and scientific papers
Synthesis and in vitro antimycobacterial activity of compounds derived from (R)- and (S)-2-amino-1-butanol - The crucial role of the configuration
Dobrikov, Georgi M.,Valcheva, Violeta,Stoilova-Disheva, Margarita,Momekov, Georgi,Tzvetkova, Pavleta,Chimov, Angel,Dimitrov, Vladimir
supporting information; experimental part, p. 45 - 56 (2012/03/26)
The synthesis of 47 structurally diverse compounds incorporating the (R)-2-amino-1-butanol motif has been realized. Ten of these compounds were found to exhibit in vitro specific activity against Mycobacterium tuberculosis H37Rv in a MIC range of 0.65 μM-14.03 μM. Five of the most active compounds 11, 22, 23, 31 and 42 (5.7-11.1 fold more active than ethambutol) can be outlined with very low cytotoxicity towards human embryonal kidney non-tumour cells (SI ranging from 91.2 to 375.4). For the purpose of comparison the (S)-enantiomers of these most active compounds have been synthesized and evaluated towards M. tuberculosis H37Rv showing no activity even at 20-32 fold higher concentrations.
Enantioselective synthesis of β-amino alcohols and α-amino acids via a copper catalyzed addition of diorganozinc reagents to N-phosphinoylimines
Desrosiers, Jean-Nicolas,C?té, Alexandre,Charette, André B.
, p. 6186 - 6192 (2007/10/03)
Enantioenriched β-amino alcohols were prepared via an asymmetric addition of diethylzinc, catalyzed by the BozPHOS·Cu(I) complex, on in situ formed N-phosphinoylimines. The nature of the hydroxyl protecting groups was found to affect the enantioselectivities. Subsequent deprotection and oxidation of N-phosphinoyl β-amino alcohols afforded optically active α-amino acids (97% ee).
