154170-05-5Relevant articles and documents
Synthesis, antimicrobial and molecular docking studies of enantiomerically pure N-alkylated β-amino alcohols from phenylpropanolamines
Chennakesava Rao,Arun,Easwaramoorthi,Balachandran,Prakasam,Eswara Yuvaraj,Perumal
, p. 3057 - 3063 (2014/06/24)
Enantiomerically pure N-alkylated β-amino alcohols 1a, 1a′, 1c, 1c′, 1d, 1d′, 1e and 1e′, with ee 100% have been synthesized from phenylpropanolamines 2. Effect of the neighboring chiral environment on the newly formed chiral center has been studied experimentally and concluded that the newly formed chiral center's absolute configuration is opposite to the adjacent (α- or β-) chiral environment. The antimicrobial activity of the synthesized β-amino alcohols were screened using in vitro disc diffusion method and variable antimicrobial activities were shown for 1a, 1a′, 1c, 1c′, 1d, 1d′, 1e & 1e′ and amongst them 1d & 1d′ exhibited significant activity against bacteria and fungi. In silico studies revealed all the synthesized β-amino alcohols 1a-e and 1a′-e′ have shown good binding energies ranging from -7.38 to -6.09 kJ/mol towards the target receptor DNA topoisomerase IV and 1d′ has shown maximum binding energy -7.38 kJ/mol.
Efficient synthesis of Ephedra alkaloid analogues using an enantiomerically pure N-[(R)-(+)-α-methylbenzyl]aziridine-2-carboxaldehyde
Hwang, Gwon-Il,Chung, Jae-Ho,Lee, Won Koo
, p. 6183 - 6188 (2007/10/03)
Efficient preparation of enantiomerically pure (2S)-aziridine-2-carboxaldehyde 9 and its 2(R) isomer and highly diastereoselective addition of organolithium reagents to the aldehyde 9 are described. The diastereoselectivity in additions of the lithium reagents seems to come from 'chelation-controlled' carbon-carbon bond formation and is influenced by the source of the organometallic compound, solvent, and the presence of a Li salt. The C(3)-N bond of the aziridine ring of the addition products was regioselectively reduced by catalytic hydrogenation in the presence of Pearlman's catalyst te provide enantiomerically pure 1,2-amino alcohols. The absolute stereochemistries of the amino alcohol 13a were assigned as (1S,2S) when the C-1 substituent was phenyl by comparison with those of commercially available norpseudoephedrine.