Synthesis and biological evaluation of modified purine homo-N-nucleosides containing pyrazole or 2-pyrazoline moiety

References

• De Clercq E. Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections. J Med Chem 1995;38:2491–517
   PubMed Web of Science ®Google Scholar
• De Clercq E. New developments in anti-HIV chemotherapy. Curr Med Chem 2001;8:1543–72
   PubMed Web of Science ®Google Scholar
• Serhan CN, Ward PA. Molecular and cellular basis of inflammation. In: Cronstein BN, ed. Current inflammation research. Ch. 12. Totowa, NJ: Humana Press Series; 1999: 259
   Google Scholar
• Cronstein BN, Kramer SB, Weissmann G, Hirschhorn R. Adenosine: a physiological modulator of superoxide anion generation by human neutrophils. J Exp Med 1983;158:1160–77
   PubMed Web of Science ®Google Scholar
• Herdewijn P. Conformationally restricted carbohydrate-modified nucleic acids and antisense technology. Biochim Biophys Acta 1999;1489:167–79
   PubMed Web of Science ®Google Scholar
• Chiacchio U, Genovese F, Iannazzo D, et al. Diastereoselective synthesis of homo-N,O-nucleosides. Tetrahedron 2004;60:441–8
   Google Scholar
• Garrido G, Gonzalez D, Delporte C, et al. Analgesic and anti-inflammatory effects of Mangifera indica L. extract (Vimang). Phytother Res 2001;15:18–21
   PubMed Web of Science ®Google Scholar
• Weber V, Coudert P, Rubat C, et al. Novel 4,5-diaryl-3-hydroxy-2(5h)-furanones as anti-oxidants and anti-inflammatory agents. Bioorg Med Chem 2002;10:1647–58
   PubMed Web of Science ®Google Scholar
• Crimmins MT. New developments in the enantioselective synthesis of cyclopentyl carbocyclic nucleosides. Tetrahedron 1998;54:9229–72
   Web of Science ®Google Scholar
• Thalassitis A, Hadjipavlou-Litina DJ, Litinas KE, Miltiadou P. 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. Bioorg Med Chem Lett 2009;19:6433–6
   PubMed Web of Science ®Google Scholar
• Muller K. 5-Lipoxygenase and 12-lipoxygenase: attractive targets for the development of novel antipsoriatic drugs. Arch Pharm (Weinheim) 1994;327:3–19
   PubMed Web of Science ®Google Scholar
• Colotta F, Allavena P, Sica A, et al. Cancer-related inflammation, the seventh hallmark of cancer: links to genetic instability. Carcinogenesis 2009;30:1073–81
   PubMed Web of Science ®Google Scholar
• Mantovani A, Allavena P, Sica A, Balkwill F. Cancer-related inflammation. Nature 2008;454:436–44
   PubMed Web of Science ®Google Scholar
• Aggarwal BB. Inflammation, a silent killer in cancer is not so silent! Curr Opin Pharmacol 2009;9:347–50
   PubMedGoogle Scholar
• Kashfi K, Enna SJ, Michael W. Anti-inflammatory agents as cancer therapeutics. Adv Pharmacol 2009;57:31–89
   PubMedGoogle Scholar
• Kumar S, Bawa S, Drabu S, et al. Recent patents on anti-infective drugs. Drug Discovery 2009;4:154–63
   Google Scholar
• Johnson M, Younglove B, Lee L, et al. Design, synthesis, and biological testing of pyrazoline derivatives of combretastatin-A4. Bioorg Med Chem Lett 2007;17:5897–901
   PubMed Web of Science ®Google Scholar
• Oezdemir Z, Kandilci HB, Guemuesel B, et al. Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-furyl)-pyrazoline derivatives. Eur J Med Chem 2007;42:373–9
   PubMedGoogle Scholar
• Elguero J. In comprehensive heterocyclic chemistry. Oxford: Pergamon Press; 1984
   Google Scholar
• Amir M, Kumar H, Khan SA. Synthesis and pharmacological evaluation of pyrazoline derivatives as new anti-inflammatory and analgesic agents. Bioorg Med Chem Lett 2008;18:918–22
   PubMed Web of Science ®Google Scholar
• Gok S, Demet MM, Ozdemir A, Turan-Zitouni G. Evaluation of antidepressant-like effect of 2-pyrazoline derivatives. Med Chem Res 2010;19:94–101
   Google Scholar
• Siddiqui AA, Rahman MA, Shaharyar M, Mishra R. Synthesis and anticonvulsant activity of some substituted 3,5-diphenyl-2-pyrazoline-1-carboxamide derivatives. Chem Sci J 2010;8:1–10
   Google Scholar
• Husain K, Abid M, Azam A. Novel Pd(II) complexes of 1-N-substituted 3-phenyl-2-pyrazoline derivatives and evaluation of antiamoebic activity. Eur J Med Chem 2008;43:393–403
   PubMedGoogle Scholar
• Shih S-R, Chu TY, Reddy GR, et al. Pyrazole compound BPR1P0034 with potent and selective anti-influenza virus activity. J Biomed Sci 2010;17:13
   PubMed Web of Science ®Google Scholar
• Abunada NM, Hassaneen HM, Abu Samaha ASM, Miqdad OA. Synthesis and antimicrobial evaluation of some new pyrazole, pyrazoline and chromeno[3,4-c]pyrazole derivatives. J Braz Chem Soc 2009;20:975–87
   Google Scholar
• Padwa A, Pearson WH, eds. Synthetic applications of 1,3-dipolar cycloaddition chemistry toward heterocycles and natural products. Hoboken, ΝJ: John Wiley & Sons; 2003
   Google Scholar
• Huisgen R. Kinetics and mechanism of 1,3-dipolar cycloadditions. Angew Chem Int Ed 1963;2:633–45
   Google Scholar
• Loupy A, ed. Microwaves in organic synthesis. Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA; 2002
   Google Scholar
• Ju Y, Varma RS. Aqueous N-heterocyclization of primary amines and hydrazines with dihalides: microwave-assisted syntheses of N-azacycloalkanes, isoindole, pyrazole, pyrazolidine, and phthalazine derivatives. J Org Chem 2006;71:135–41
   PubMed Web of Science ®Google Scholar
• Kost AN, Grandberg II. Progress in pyrazole chemistry. Adv Heterocycl Chem 1966;6:347–429
   Google Scholar
• Corradi A, Leonelli C, Rizzuti A, et al. New “Green” approaches to the synthesis of pyrazole derivatives. Molecules 2007;12:1482–95
   PubMed Web of Science ®Google Scholar
• Fulton JR, Aggarwal VK, De Vicente J. The use of tosylhydrazone salts as a safe alternative for handling diazo compounds and their applications in organic synthesis. Eur J Org Chem 2005;1479–92
   Google Scholar
• Aggarwal VK, De Vicente J, Bonnert RV. A novel one-pot method for the preparation of pyrazoles by 1,3-dipolar cycloadditions of diazo compounds generated in situ. J Org Chem 2003;68:5381–3
   PubMed Web of Science ®Google Scholar
• Symeonidis T, Chamilos M, Hadjipavlou-Litina DJ, et al. Synthesis of hydroxycoumarins and hydroxybenzo[f]-or [h]coumarins as lipid peroxidation inhibitors. Bioorg Med Chem Lett 2009;19:1139–42
   PubMed Web of Science ®Google Scholar
• Michaelidou A, Hadjipavlou-Litina DJ, Matsini I, Tsitsogianni E. Heterocyclic aryl(phenyl)acetic acid and aryl acetohydroxamic acids as antiinflammatory antioxidant agents and inhibitors of lipoxygenase and serine proteases. Med Chem 2007;3:439–45
   PubMedGoogle Scholar
• Dimas K, Papadaki M, Tsimplouli C, et al. Labd-14-ene-8,13-diol (sclareol) induces cell cycle arrest and apoptosis in human breast cancer cells and enhances the activity of anticancer drugs. Biomed Pharmacother 2006;60:127–33
   PubMedGoogle Scholar
• Dimas K, Demetzos C, Mitaku S, et al. Cytotoxic activity of kaempferol glycosides against human leukaemic cell lines in vitro. Pharm Res 2000;41:85–8
   Google Scholar
• Dimas K, Hatziantoniou S, Tseleni S, et al. Sclareol induces apoptosis in human HCT116 colon cancer cells in vitro and suppression of HCT116 tumor growth in immunodeficient mice. Apoptosis 2007;12:685–94
   PubMed Web of Science ®Google Scholar
• Biobyte Corp. C-QSAR database. Claremont CA, CSlifornia. Available form: www.biobyte.com
   Google Scholar
• De la Cruz P, Diaz-Ortiz A, Garcia JJ, et al. Synthesis of new C-60-donor dyads by reaction of pyrazolylhydrazones with [60]fullerene under microwave irradiation. Tetrahedron Lett 1999;40:1587–90
   Web of Science ®Google Scholar
• Huisgen R, Seidel M, Wallbillich G, Knupfer H. Diphenyl-nitrilimin und seine 1.3-dipolaren additionen an alkene und alkine. Tetrahedron 1962;17:3–29
   Google Scholar
• Nigam S, Schewe T. Phospholipase A(2)S and lipid peroxidation. Biochim Biophys Acta 2000;1488:167–81
   PubMed Web of Science ®Google Scholar
• Kulisic T, Radonic A, Katalinic V, Milos M. Use of different methods for testing antioxidative activity of oregano essential oil. Food Chem 2004;85:633–40
   Web of Science ®Google Scholar
• Molyneux P. The use of the stable free radical diphenylpicrylhydrazyl (DPPH) for estimating antioxidant activity. Songklanakarin J Sci Technol 2004;26:211–19
   Google Scholar
• Koleva II, Van Beek TA, Linssen JPH, et al. Screening of plant extracts for antioxidant activity: a comparative study on three testing methods. Phytochem Anal 2001;13:8–17
   Web of Science ®Google Scholar
• Liegois C, Lermusieau G, Colin S. Measuring antioxidant efficiency of wort, malt, and hops against the 2,2′-azobis(2-amidinopropane) dihydrochloride-induced oxidation of an aqueous dispersion of linoleic acid. J Agric Food Chem 2000;48:1129–34
   PubMed Web of Science ®Google Scholar
• Pontiki E, Hadjipavlou-Litina D. Review in QSARs on LOX inhibitors. Mini Rev Med Chem 2003;3:487–99
   PubMed Web of Science ®Google Scholar
• Pontiki E, Hadjipavlou-Litina D. Quantitative Structure Activity Relationships (QSARs) on lipoxygenase inhibitors. Curr Med Chem – Anti-Inflammatory Anti-Allergy Agents 2004;3:139–56
   Google Scholar
• Pontiki E, Hadjipavlou-Litina D. Lipoxygenase inhibitors: A comparative QSAR study review and evaluation of new QSARs. Med Res Rev 2008;28:39–117
   PubMed Web of Science ®Google Scholar
• Viles-Gonzalez JF, Badimon JJ. Atherothrombosis: the role of tissue factor. Int J Biochem Cell Biol 2004;36:25–30
   PubMed Web of Science ®Google Scholar
• Maraganore MD. Thrombin, thrombin inhibitors, and the arterial thrombotic process. Thromb Haemostasis 1993;70:208–11
   PubMed Web of Science ®Google Scholar
• Nyby MD, Sasaki M, Ideguchi Y, et al. Platelet lipoxygenase inhibitors attenuate thrombin- and thromboxane mimetic-induced intracellular calcium mobilization and platelet aggregation. J Pharm Exp Therap 1996;278:503–9
   PubMed Web of Science ®Google Scholar