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Relevant academic research and scientific papers

Stereoselective synthesis of trans- and cis-2-aryl-3-(hydroxymethyl) aziridines through transformation of 4-aryl-3-chloro-β-lactams and study of their ring opening

trans- and cis-1-Alkyl-4-aryl-3-chloroazetidin-2-ones, prepared through cyclocondensation of chloroketene and the appropriate imines in a diastereoselective way, were transformed into the corresponding non-activated trans- and cis-2-aryl-3-(hydroxymethyl)aziridines via reductive ring contraction using LiAlH4 in Et2O. Furthermore, trans-2-aryl-3- (hydroxymethyl)aziridines were transformed into 2-amino-3-arylpropan-1-ols and anti-2-amino-3-aryl-3-methoxypropan-1-ols by means of an unprecedented ring opening by LiAlH4 and by MeOH, respectively. cis-2-Aryl-3- (hydroxymethyl)aziridines were shown to be highly reluctant to undergo ring opening by LiAlH4 and MeOH under similar reaction conditions.

Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3- triazoles and evaluation of their antimalarial activity

A variety of 2-amino-3-arylpropan-1-ols, anti-2-amino-3-aryl-3- methoxypropan-1-ols and anti-2-amino-1-arylpropan-1,3-diols were prepared selectively through elaboration of trans-4-aryl-3-chloro-β-lactams. In addition, a number of 2-(azidomethyl)-aziridines was converted into novel 2-[(1,2,3-triazol-1-yl)methyl]aziridines by Cu(I)-catalyzed azide-alkyne cycloaddition, followed by microwave-assisted, regioselective ring opening by dialkylamine towards 1-(2,3-diaminopropyl)-1,2,3-triazoles. Although most of these compounds exhibited weak antiplasmodial activity, six representatives showed moderate antiplasmodial activity against both a chloroquine-sensitive and a chloroquine-resistant strain of Plasmodium falciparum with IC 50-values of 25 μM.