Synthesis, antimicrobial and molecular docking studies of enantiomerically pure N-alkylated β-amino alcohols from phenylpropanolamines

Article abstract of DOI:10.1016/j.bmcl.2014.05.027

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.