期刊
BIOMOLECULES
卷 10, 期 1, 页码 -出版社
MDPI
DOI: 10.3390/biom10010095
关键词
lactones; halolactonisation; kinetic resolution ofalcohols; antimicrobial activity; antiproliferative activity; hemolytic activity; erythrocytes; biological membranes
资金
- Department of Chemistry, Wroclaw University of Environmental and Life Sciences
Starting from 1-acetyl-1-cyclohexene, three enantiomeric pairs (ee >= 99%) of bicyclic delta-halo-gamma-lactones with cyclohexane ring were obtained in five-step synthesis. The key stereochemical steps were lipase-catalyzed kinetic resolution of racemic 1-(cyclohex-1-en-1-yl) ethanol followed by transfer of chirality to ethyl 2-(2-ethylidenecyclohexyl) acetate in the Johnson-Claisen rearrangement. Synthesized halolactones exhibited antiproliferative activity towards canine B-cell leukemia cells (GL-1) and canine B-cell chronic leukemia cells (CLB70) and the most potent (IC50 18.43 +/- 1.46 mu g/mL against GL-1, IC50 11.40 +/- 0.40 mu g/mL against CLB70) comparable with the control etoposide, was (1R,6R,1 ' S)-1-(1 '-chloroethyl)-9-oxabicyclo[4.3.0]nonan-8-one (8b). All halolactones did not have a toxic effect on erythrocytes and did not change the fluidity of membranes in the hydrophobic region of the lipid bilayer. Only weak changes in the hydrophilic area were observed, like the degree of lipid packing and associated hydration. The racemic halolactones were also tested for their antimicrobial properties and found to exhibit selectivity towards bacteria, in particular, towards Proteus mirabilis ATCC 35659.
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