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Research Article

Synthesis and theoretical calculations of carbazole substituted chalcone urea derivatives and studies their polyphenol oxidase enzyme activity

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Pages 808-815 | Received 28 Feb 2012, Accepted 14 Apr 2012, Published online: 18 Jul 2012

References

  • Okot-Kotber M, Liavoga A, Yong KJ, Bagorogoza K. Activation of polyphenol oxidase in extracts of bran from several wheat (Triticum aestivum) cultivars using organic solvents, detergents, and chaotropes. J Agric Food Chem 2002;50:2410–2417.
  • Yan Q, Cao R, Yi W, Yu L, Chen Z, Ma L et al. Synthesis and evaluation of 5-benzylidene(thio)barbiturate-beta-D-glycosides as mushroom tyrosinase inhibitors. Bioorg Med Chem Lett 2009;19:4055–4058.
  • Friedman M. Food browning and its prevention: An overview. J Agric Food Chem 1996;44:631–653.
  • Vámos-Vigyázó L. Polyphenol oxidase and peroxidase in fruits and vegetables. Crit Rev Food Sci Nutr 1981;15:49–127.
  • Di Carlo G, Mascolo N, Izzo AA, Capasso F. Flavonoids: old and new aspects of a class of natural therapeutic drugs. Life Sci 1999;65:337–353.
  • Chang TS. An updated review of tyrosinase inhibitors. Int J Mol Sci 2009;10:2440–2475.
  • Anto RJ, Sukumaran K, Kuttan G, Rao MN, Subbaraju V, Kuttan R. Anticancer and antioxidant activity of synthetic chalcones and related compounds. Cancer Lett 1995;97:33–37.
  • Lahtchev KL, Batovska DI, Parushev SP, Ubiyvovk VM, Sibirny AA. Antifungal activity of chalcones: a mechanistic study using various yeast strains. Eur J Med Chem 2008;43:2220–2228.
  • Go ML, Wu X, Liu XL. Chalcones: an update on cytotoxic and chemoprotective properties. Curr Med Chem 2005;12:481–499.
  • Batovska D, Parushev S, Stamboliyska B, Tsvetkova I, Ninova M, Najdenski H. A series of 3-unsubstituted/substituted-4,5-diphenyl-2-oxo-3 H-1,3-oxazole derivatives. Europ J Med Chem 2009;44:2211–2218.
  • Sogawa S, Nihro Y, Ueda H, Miki T, Matsumoto H, Satoh T. Protective effects of hydroxychalcones on free radical-induced cell damage. Biol Pharm Bull 1994;17:251–256.
  • Lee SH, Seo GS, Kim HS, Woo SW, Ko G, Sohn DH. 2′,4′,6′-Tris(methoxymethoxy) chalcone attenuates hepatic stellate cell proliferation by a heme oxygenase-dependent pathway. Biochem Pharmacol 2006;72:1322–1333.
  • Nerya O, Musa R, Khatib S, Tamir S, Vaya J. Chalcones as potent tyrosinase inhibitors: the effect of hydroxyl positions and numbers. Phytochemistry 2004;65:1389–1395.
  • Miranda CL, Aponso GL, Stevens JF, Deinzer ML, Buhler DR. Prenylated chalcones and flavanones as inducers of quinone reductase in mouse Hepa 1c1c7 cells. Cancer Lett 2000;149:21–29.
  • Demir D, Gençer N, Arslan O, Genç H, Zengin M. In vitro inhibition of polyphenol oxidase by some new diarylureas. J Enzyme Inhib Med Chem 2012;27:125–131.
  • Sonmez F, Sevmezler S, Atahan A, Ceylan M, Demir D, Gencer N et al. Evaluation of new chalcone derivatives as polyphenol oxidase inhibitors. Bioorg Med Chem Lett 2011;21:7479–7482.
  • Quiroga J, Trilleras J, Abonía R, Insuasty B, Nogueras M, Cobo J, Torrec JM. 4-aminopyridine-5-carbaldehydes as intermediates in a friedlander type synthesis of 7-arylpyrido[2,3-D]pyrimidines. arkivoc 2009;xiv:9–27.
  • Tu S, Li, C, Shi, F, Zhou, D, Shao, Q, Cao, L, Jiang, B. An efficient chemoselective synthesis of pyrido[2,3-d]pyrimidine derivatives under microwave irradiation. Synthesis 2008;3:369–372.
  • Devi, I, Borah, HN, Bhuyan, PJ. Studies on uracils: a facile one-pot synthesis of oxazino[4,5-d]-,pyrano[2,3-d]-, pyrido[2,3-d]- and pyrimido[4,5-d]pyrimidines using microwave irradiation in the solid state. Tetrahedron Lett. 2004;45:2405–2410.
  • Tang, H, Zhang, Z, Cong, C, Zhang, K. Potential application as optoelectronic material Russ J. of Org. Chem. 2009;45:559–563.
  • Wesche-Ebeling P, Montgomery MW. Strawberry polyphenol oxidase: extraction and partial characterization. J Food Sci 1990;55:1320–1325.
  • Arslan O, Erzengin M, Sinan S, Ozensoy O. Purification of mulberry (Morus alba L.) polyphenol oxidase by affinity chromatography and investigation of its kinetic and electrophoretic properties. Food Chem 2004;88:479–484.
  • Espin JC, Morales M, Varon R, Tudela J, Garcia-Canovas F. A continuous spectrophotometric method for determining the monophenolase and diphenolase activities of apple polyphenol oxidase. Anal Biochem 1995;43:2807–2812.
  • Sayaverde-Soto LA, Montgomery MW. Inhibition of polyphenol oxidase by sulfite. J. Food Sci. 1986;51:1531–1535.
  • Embs RJ, Markakis P. The mechanism of sulphite inhibition of browning caused by polyphenol oxidase. J. Food Sci. 1965;30:753–758.
  • Schwimmer S, Schwimmer S. (ed) Source Book of Food Enzymology. AVI Publishing, Westport. 1981;274:267
  • Chilaka FC, Eze S, Anyadiegwu C, Uvere PO. Browning in processed yams: peroxidase or polyphenol oxidase? J. of the Science of Food and Agriculture 2002;82:899–903.
  • Güllçin I, Küfrevioglu OI, Oktay M. Purification and characterization of polyphenol oxidase from nettle (Urtica dioica L.) and inhibitory effects of some chemicals on enzyme activity. J Enzyme Inhib Med Chem 2005;20:297–302.
  • Ryazanova AD, Alekseev AA, Slepneva IA. The phenylthiourea is a competitive inhibitor of the enzymatic oxidation of DOPA by phenoloxidase. J Enzyme Inhib Med Chem 2012;27:78–83.
  • Gheibi N, Saboury AA, Haghbeen K, Rajaei F, Pahlevan AA. Dual effects of aliphatic carboxylic acids on cresolase and catecholase reactions of mushroom tyrosinase. J Enzyme Inhib Med Chem 2009;24:1076–1081.
  • Alijanianzadeh M, Saboury AA, Mansuri-Torshizi H, Haghbeen K, Moosavi-Movahedi AA. The inhibitory effect of some new synthesized xanthates on mushroom tyrosinase activities. J Enzyme Inhib Med Chem 2007;22:239–246.
  • Gacche RN, Gond DS, Dhole NA, Dawane BS. Coumarin Schiff-bases: as antioxidant and possibly anti-inflammatory agents. J Enzyme Inhib Med Chem 2006;21:157–161.
  • Gheibi N, Saboury AA, Mansuri-Torshizi H, Haghbeen K, Moosavi-Movahedi AA. The inhibition effect of some n-alkyl dithiocarbamates on mushroom tyrosinase. J Enzyme Inhib Med Chem 2005;20:393–399.
  • (a) Gaussian 09, Revision A.1, Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Scalmani, G, Barone, V, Mennucci, B, Petersson, G. A, Nakatsuji, H, Caricato, M, Li, X, Hratchian, H. P, Izmaylov, A. F, Bloino, J, Zheng, G, Sonnenberg, J. L, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Vreven, T, Montgomery, J. A. Jr, Peralta, J. E, Ogliaro, F, Bearpark, M, Heyd, J. J, Brothers, E, Kudin, K. N, Staroverov, V. N, Kobayashi, R, Normand, J, Raghavachari, K, Rendell, A, Burant, J. C, Iyengar, S. S, Tomasi, J, Cossi, M, Rega, N, Millam, J. M, Klene, M, Knox, J. E, Cross, J. B, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Martin, R. L, Morokuma, K, Zakrzewski, V. G, Voth, G. A, Salvador, P, Dannenberg, J. J, Dapprich, S, Daniels, A. D, Farkas, O, Foresman, J. B, Ortiz, J. V, Cioslowski, J, Fox, D. J, Gaussian, Inc, Wallingford CT, 2009. (b) GaussView, Version 5, Dennington, R, Keith, T, Millam, J, Semichem. Inc., Shawnee Mission KS, 2009.
  • Ohno S, Matsumoto N, Watanabe M, Nakajin S. Flavonoid inhibition of overexpressed human 3beta-hydroxysteroid dehydrogenase type II. J Steroid sBiochem Mol Biol 2004;88:175–182.

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