776
Views
5
CrossRef citations to date
0
Altmetric
Research Article

Synthesis, antielastase, antioxidant and radical scavenging activities of 4-(aza substituted) methylene substituted dihydroxy coumarines

, , , , , & show all
Pages 870-875 | Received 30 Mar 2012, Accepted 04 May 2012, Published online: 18 Jul 2012

References

  • Aruoma IO, Cuppette SL. Antioxidant methodology: in vivo and in vitro concepts. Illinois: AOAS Press 1997.
  • Prakash D, Upadhyay G, Singh BN, Sing HB. Antioxidant and free radical-scavenging activities of seeds anda gri-wastes of some varieties of soybean (Glycine Max). Food Chem 2007; 104:783–790.
  • Hussain HH, Babic G, Durst T, Wright JS, Flueraru M, Chichirau A et al. Development of novel antioxidants: design, synthesis, and reactivity. J Org Chem 2003;68:7023–7032.
  • Siedle LG, Gustavsoon L, Johansson S, Murillo R, Castro V, Bohlin L, Merfot I. The effect of sesquiterpene lactones on the release of human neutrophil elastase. Biochem Pharmacol 2003; 65: 897–903.
  • Siedle B, Hrenn A, Merfort I. Natural compounds as inhibitors of human neutrophil elastase. Planta Med 2007;73:401–420.
  • Khlebnikov AI, Schepetkin IA, Quinn MT. Structure-activity relationship analysis of N-benzoylpyrazoles for elastase inhibitory activity: a simplified approach using atom pair descriptors. Bioorg Med Chem 2008;16:2791–2802.
  • Abboud RT, Vimalanathan S. Pathogenesis of COPD. Part I. The role of protease-antiprotease imbalance in emphysema. Int J Tuberc Lung Dis 2008;12:361–367.
  • Voynow JA, Fischer BM, Zheng S. Proteases and cystic fibrosis. Int J Biochem Cell Biol 2008;40:1238–1245.
  • Hashimoto S, Okayama Y, Shime N, Kimura A, Funakoshi Y, Kawabata K et al. Neutrophil elastase activity in acute lung injury and respiratory distress syndrome. Respirology 2008;13:581–584.
  • Uchida Y, Freitas MC, Zhao D, Busuttil RW, Kupiec-Weglinski JW. The protective function of neutrophil elastase inhibitor in liver ischemia/reperfusion injury. Transplantation 2010;89:1050–1056.
  • Melagraki G, Afantitis A, Igglessi-Markopoulou O, Detsi A, Koufaki M, Kontogiorgis C et al. Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3-aminoamides and their α-lipoic acid adducts. Eur J Med Chem 2009;44:3020–3026.
  • Maxwell A. The interaction between coumarin drugs and DNA gyrase. Mol Microbiol 1993;9:681–686.
  • Musicki B, Periers AM, Laurin P, Ferroud D, Benedetti Y, Lachaud S et al. Improved antibacterial activities of coumarin antibiotics bearing 5′,5′-dialkylnoviose: biological activity of RU79115. Bioorg Med Chem Lett 2000;10:1695–1699.
  • Chimichi S, Boccalini M, Cosimelli B, Viola G, Vedaldi D, Dall’Acqua F. New geiparvarin analogues from 7-(2-oxoethoxy)coumarins as efficient in vitro antitumoral agents. Tetrahedron Lett 2002; 43: 7473–7476.
  • Yoakim C, Bonneau PR, Déziel R, Doyon L, Duan J, Guse I et al. Novel nevirapine-like inhibitors with improved activity against NNRTI-resistant HIV: 8-heteroarylthiomethyldipyridodiazepinone derivatives. Bioorg Med Chem Lett 2004;14:739–742.
  • Uchiumi F, Hatano T, Ito H, Yoshida T, Tanuma S. Transcriptional suppression of the HIV promoter by natural compounds. Antiviral Res 2003;58:89–98.
  • Yu D, Suzuki M, Xie L, Morris-Natschke SL, Lee KH. Recent progress in the development of coumarin derivatives as potent anti-HIV agents. Med Res Rev 2003;23:322–345.
  • Jeddy AS, Gleason BL. Aspirin and warfarin versus aspirin monotherapy after myocardial infarction. Ann Pharmacother 2003;37:1502–1505.
  • Pineo G, Hull RD. Coumarin therapy in thrombosis. Hematol Oncol Clin North Am 2003;17:201–16, viii.
  • Guiotto A, Chilin A, Manzini P, Dall’Acqua F, Bordin F, Rodighiero P. Synthesis and antiproliferative activity of furocoumarin isosters. Farmaco 1995;50:479–488.
  • Kontogiorgis CA, Hadjipavlou-Litina DJ. Synthesis and biological evaluation of novel coumarin derivatives with a 7-azomethine linkage. Bioorg Med Chem Lett 2004;14:611–614.
  • Kamal A, Adil SF, Tamboli JR, Siddardha B, Murthy USN. Synthesis of cyclodextrin derivatives of amino-(thiazolyl) coumarins as potential antimicrobial agents. Lett Drug Des Discov 2009; 6: 201–209.
  • Ito C, Itoigawa M, Mishina Y, Filho VC, Enjo F, Tokuda H et al. Chemical constituents of Calophyllum brasiliense. 2. Structure of three new coumarins and cancer chemopreventive activity of 4-substituted coumarins. J Nat Prod 2003;66:368–371.
  • Kontogiorgis CA, Hadjipavlou-Litina DJ. Synthesis and antiinflammatory activity of coumarin derivatives. J Med Chem 2005;48:6400–6408.
  • Ghate M, Manohar D, Kulkarni V, Shobha R, Kattimani SY. Synthesis of vanillin ethers from 4-(bromomethyl) coumarins as anti-inflammatory agents. Eur J Med Chem 2003;38:297–302.
  • Silván AM, Abad MJ, Bermejo P, Sollhuber M, Villar A. Antiinflammatory activity of coumarins from Santolina oblongifolia. J Nat Prod 1996;59:1183–1185.
  • Kulkarni GM, Kulkarni MV, Patil VD. ChemInform Abstract: Synthesis and antiinflammatory activity of some new triheterocyclic thiazoles. Rev Roum Chim. 1990; 35: 549–554.
  • Deana AA, Stokker GE, Schultz EM, Smith RL, Cragoe EJ Jr, Russo HF et al. 2-(Aminomethyl)phenols, a new class of saluretic agents. 5. Fused-ring analogues. J Med Chem 1983;26:580–585.
  • Tyagi YK, Kumar A, Raj HG, Vohra P, Gupta G, Kumari R, Kumar P, Gupta RK. Synthesis of novel amino and acetyl amino-4-methyl coumarins and evaluation of their antioxidant activity. Eur J Med Chem 2005;40:413–420.
  • Gumus A, Karadeniz S, Ugras HI, Bulut M, Cakir U, Goren AC. Synthesis, complexation, and biological activity studies of 4-aminomethyl-7,8-dihydroxy coumarines and their crown ether derivatives. J Heterocyclic Chem 2010; 47: 1127–1133.
  • Brands-Williams W, Cuvelier ME, Berset C. Use of a free radical method to evaluate antioxidant activity. Lebensm-Wiss Technol 1995; 28: 25–30.
  • Arnao MB, Cano A, Acosta M. The hydrophilic and lipophilic contribution to total antioxidant activity. Food Chem 2001; 3: 239–244.
  • Oyaizu M. Studies on product of browning reaction prepared from glucose amine. Jap J Nutr 1986; 44: 307–315.
  • Apak R, Güçlü K, Ozyürek M, Esin Karademir S, Erçag E. The cupric ion reducing antioxidant capacity and polyphenolic content of some herbal teas. Int J Food Sci Nutr 2006;57:292–304.
  • James AE, Timothy DW, Gordon L. Inhibition of human leukocyte and pancreatic elastase by homologues of bovine pancreatic trypsin inhibitors. Biochemistry 1996; 35: 9090–9096.
  • Soares JR, Dinis TC, Cunha AP, Almeida LM. Antioxidant activities of some extracts of Thymus zygis. Free Radic Res 1997;26:469–478.
  • Villaño D, Fernández-Pachón MS, Moyá ML, Troncoso AM, García-Parrilla MC. Radical scavenging ability of polyphenolic compounds towards DPPH free radical. Talanta 2007;71:230–235.
  • Leong LP, Shui G. An investigation of antioxidant capacity of fruits in Singapore markets. Food Chem 2002; 76: 69–75.
  • Halliwell B, Gutteridge JM. Oxygen toxicity, oxygen radicals, transition metals and disease. Biochem J 1984;219:1–14.
  • Peksel A, Celik C, Ocal N, Yanardag R. Antioxidant and radical scavenging activities of some norcantharidin and bridged perhydroisoindole derivatives. J Serbian Chem Soc 2012;77. DOI: 10.2298/JSC120123036P.
  • Köksal E, Gülçin I, Beyza S, Sarikaya O, Bursal E. In vitro antioxidant activity of silymarin. J Enzyme Inhib Med Chem 2009;24:395–405.
  • Pochet L, Frédérick R, Masereel B. Coumarin and isocoumarin as serine protease inhibitors. Curr Pharm Des 2004;10:3781–3796.
  • Pochet L, Doucet C, Dive G, Wouters J, Masereel B, Reboud-Ravaux M et al. Coumarinic derivatives as mechanism-based inhibitors of α-chymotrypsin and human leukocyte elastase. Bioorg Med Chem 2000;8:1489–1501.
  • Bissonnette EY, Tremblay GM, Turmel V, Pirotte B, Reboud-Ravaux M. Coumarinic derivatives show anti-inflammatory effects on alveolar macrophages, but their anti-elastase activity is essential to reduce lung inflammation in vivo. Int Immunopharmacol 2009;9:49–54.
  • Sokmen BB, Gumrukcuoglu N, Ugras S, Ugras HI, Yanardag R. Synthesis, antibacterial, antielastase, antiurease and antioxidant activities of new methoxy substitued bis-1,2,4-triazole derivatives. J Enzyme Inhib Med Chem doi:10.3109/14756366.2011.631536

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.