Synthesis of modified homo-N-nucleosides from the reactions of mesityl nitrile oxide with 9-allylpurines and their influence on lipid peroxidation and thrombin inhibition.
9-(3-Mesityl-4,5-dihydroisoxazol-5-yl) homo-N-nucleosides were prepared from the 1,3-dipolar cycloaddition 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.
Thalassitis
Andreas
A
Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece.
Hadjipavlou-Litina
Dimitra J
DJ
Litinas
Konstantinos E
KE
Miltiadou
Panagiotis
P
D000975:Antioxidants / Q000378:metabolism / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000737:chemistry; D006588:Hexanones / Q000737:chemistry; D015227:Lipid Peroxidation / Q000187:drug effects*; D009570:Nitriles / Q000737:chemistry; D009705:Nucleosides / Q000737:chemistry*; D011687:Purines / Q000737:chemistry*; D013481:Superoxides / Q000737:chemistry; D013917:Thrombin / Q000037:antagonists & inhibitors* / Q000737:chemistry
D000975:Antioxidants; D016166:Free Radical Scavengers; D006588:Hexanones; D009570:Nitriles; D009705:Nucleosides; D011687:Purines; D013481:Superoxides; C008374:mesityl oxide; D013917:Thrombin; C079308:6-chloropurine