Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 19, Issue 22, Pages 6433-6436Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2009.09.040
Keywords
Homo-N-nucleosides; 9-Allylpurines; Lipid peroxidation inhibitors; Thrombin inhibitors; 1,3-Dipolar cycloaddition reaction; Mesityl nitrile oxide
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9-(3-Mesityl-4,5-dihydroisoxazol-5-yl) homo-N-nucleosides were prepared from the 1,3-dipolar cyclo-addition reactions of mesityl nitrile oxide with 9-allyl derivatives of 6-chloropurine, 6-piperidinylpurine, 6-morpholinylpurine, 6-pyrrolidinylpurine, and 6-N,N-dibenzoyladenine. The new compounds were tested in vitro for their ability: (i) to interact with 1,1-diphenyl-2-picryl-hydrazyl (DPPH) stable free radical, (ii) to inhibit lipid peroxidation, (iii) to scavenge the superoxide anion, (iv) to inhibit the activity of soybean lipoxygenase, and (v) to inhibit in vitro thrombin. Most of them found to be potent thrombin inhibitors and to inhibit in vitro lipid peroxidation. The majority of the compounds showed significant lipoxygenase inhibitory activity. (C) 2009 Elsevier Ltd. All rights reserved.
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