Abstract
Introduction:The 1,3-dipolar cycloaddition reactions of nitrile oxides formed in situ (in the presence of NCS and Et3N) from the oximes of (purin-9-yl)acetaldehyde or (coumarinyloxy)acetaldehyde with allyloxycoumarins or 9-allylpurines, respectively resulted in 3,5-disubstituted isoxazolines. The similar reactions of propargyloxycoumarins or 9-propargylpurines led to 3,5-disubstituted isoxazoles by treatment with PIDA and catalytic amount of TFA.Methods:The new compounds were tested in vitro as antioxidant agents and inhibitors of soybean lipoxygenase LO, AChE and MAO-B.Results:The majority of the compounds showed significant hydroxyl radical scavenging activity. Compounds 4k and 4n presented LO inhibitory activity.Conclusion:Compound 13e presents an antioxidant significant profile combining anti-LO, anti-AChE and anti-MAO-B activities.
Highlights
The 1,3-dipolar cycloaddition reactions of nitrile oxides formed in situ from the oximes ofacetaldehyde oracetaldehyde with allyloxycoumarins or 9-allylpurines, respectively resulted in 3,5disubstituted isoxazolines
The Open Medicinal Chemistry Journal, 2017, Volume 11 197 derivatives [3, 14, 15] and on modified nucleosides [16, 17], we present here the synthesis of new conjugated molecules as modified nucleosides, combining the coumarin and purine moieties through isoxazolines or isoxazoles as spacers
The new compounds were investigated for their antioxidant profile [free radical scavengers, lipid peroxidation and lipoxygenase (LO) inhibitors] as well as for their activity to ChEs and MAO enzymes searching for multipotent compounds
Summary
The 1,3-dipolar cycloaddition reactions of nitrile oxides formed in situ (in the presence of NCS and Et3N) from the oximes of (purin-9-yl)acetaldehyde or (coumarinyloxy)acetaldehyde with allyloxycoumarins or 9-allylpurines, respectively resulted in 3,5disubstituted isoxazolines. Modified nucleosides [1, 2], coumarin derivatives [3 - 5], isoxazolines [6] and isoxazoles [7] represent classes of compounds with interesting broad range biological activities. In continuation to our recent studies on hybrid molecules with purine and coumarin moieties [11 - 13], on coumarin. Hybrid Molecules with Purine, Coumarin and Isoxazoline or Isoxazole. The Open Medicinal Chemistry Journal, 2017, Volume 11 197 derivatives [3, 14, 15] and on modified nucleosides [16, 17], we present here the synthesis of new conjugated molecules as modified nucleosides, combining the coumarin and purine moieties through isoxazolines or isoxazoles as spacers. The new compounds were investigated for their antioxidant profile [free radical scavengers, lipid peroxidation and lipoxygenase (LO) inhibitors] as well as for their activity to ChEs and MAO enzymes searching for multipotent compounds
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