Document Detail

Synthesis and biological evaluation of modified purine homo-N-nucleosides containing pyrazole or 2-pyrazoline moiety.
MedLine Citation:
PMID:  23339428     Owner:  NLM     Status:  Publisher    
Abstract 9-Substituted (pyrazol-5-yl)methyl- or (2-pyrazolin-5-yl)methyl-9H-purines were synthesized from 9-allyl-6-chloro-9H-purine through the 1,3-dipolar cycloaddition reaction with nitrile imines, prepared in situ from the corresponding hydrazone and NBS/Et(3)N under MW or from hydrazinoylchloride and Et(3)N under reflux. The coupling of new 6-chloropurines with amines in H(2)O under microwaves resulted quantitatively to modified pyrazol-5-yl- or 2-pyrazolin-5-yl adenine homo-N-nucleosides. The new compounds were tested in vitro for their ability to: (i) interact with 1,1-diphenyl-2-picryl-hydrazyl (DPPH), (ii) inhibit lipid peroxidation, (iii) inhibit the activity of soybean lipoxygenase, (iv) inhibit in vitro thrombin and for (v) their antiproliferative and cytotoxic activity. Pyrazolines were found to be more potent in vitro. Compound 7a exhibited satisfactory combined antioxidant and anti-lipid peroxidation activity, inhibition of lipoxygenase (89%) and thrombin inhibitory ability, whereas compound 7b exhibited high lipoxygenase inhibitory activity in combination to significant anti-thrombin activity. No compound exhibited a significant cytotoxic activity, while all showed moderate antiproliferative activity.
Andreas Thalassitis; Anna-Maria Katsori; Konstantinos Dimas; Dimitra J Hadjipavlou-Litina; Fokion Pyleris; Nikolaos Sakellaridis; Konstantinos E Litinas
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2013-1-23
Journal Detail:
Title:  Journal of enzyme inhibition and medicinal chemistry     Volume:  -     ISSN:  1475-6374     ISO Abbreviation:  J Enzyme Inhib Med Chem     Publication Date:  2013 Jan 
Date Detail:
Created Date:  2013-1-23     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101150203     Medline TA:  J Enzyme Inhib Med Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki , Thessaloniki , Greece .
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