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Research Article

Design, synthesis and bioevaluation of novel umbelliferone analogues as potential mushroom tyrosinase inhibitors

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Pages 874-883 | Received 04 Sep 2014, Accepted 17 Oct 2014, Published online: 03 Feb 2015

References

  • Sánchez-Ferrer A, Rodríguez-López JN, García-Cánovas F, GarcíaCarmona F. Tyrosinase: a comprehensive review of its mechanism. Biochim Biophys Acta 1995;1247:1–11
  • Matsuura R, Ukeda H, Sawamura M. Tyrosinase inhibitory activity of citrus essential oils. J Agric Food Chem 2006;54:2309–13
  • Tripathi RK, Hearing VJ, Urabe K, et al. Mutational mapping of the catalytic activities of human tyrosinase. J Biol Chem 1992;267:23707–12
  • Schallreuter KU, Hasse S, Rokos H, et al. Cholesterol regulates melanogenesis in human epidermal melanocytes and melanoma cells. Exp Dermatol 2009;18:680–8
  • Wood JM, Decker H, Hartmann H, et al. Senile hair graying: H2O2-mediated oxidative stress affects human hair colour by blunting methionine sulfoxide repair. FASEB J 2009;23:2065–75
  • Thanigaimalai P, Hoang TAL, Lee KC, et al. Structural requirement(s) of N-phenylthioureas and benzaldehyde thiosemicarbazones as inhibitors of melanogenesis in melanoma B16 cells. Bioorg Med Chem Lett 2010;20:2991–3
  • Yi W, Cao R, Peng W, et al. Synthesis and biological evaluation of novel 4-hydroxybenzaldehyde derivatives as tyrosinase inhibitors. Eur J Med Chem 2010;45:639–46
  • Seo SY, Sharma VK, Sharma N. Mushroom tyrosinase: recent prospects. J Agric Food Chem 2003;51:2837–53
  • Zhu YJ, Zhou HT, Hu YH, et al. Antityrosinase and antimicrobial activities of 2-phenylethanol, 2-phenylacetaldehyde and 2-phenylacetic acid. Food Chem 2011;124:298–302
  • Loizzo MR, Tundis R, Menichini F. Natural and synthetic tyrosinase inhibitors as antibrowning agents: an update. Compr Rev Food Sci Food Safety 2012;11:378–98
  • Chang TS. An updated review of tyrosinase inhibitors. Int J Mol Sci 2009;10:2440–75
  • Khan MTH. Molecular design of tyrosinase inhibitors: a critical review of promising novel inhibitors from synthetic origins. Pure Appl Chem 2007;79:2277–95
  • Masamoto Y, Murata Y, Baba K, et al. Inhibitory effects of esculetin on melanin biosynthesis. Biol Pharm Bull 2004;27:422–5
  • Bourgaud F, Hehn A, Larbat R, et al. Biosynthesis of coumarins in plants a major pathway still to be unravelled for cytochrome P450 enzymes. Phytochem Rev 2006;5:293–308
  • Mueller RL. First-generation agents: aspirin, heparin and coumarins. Best Pract Res Clin Haematol 2004;17:23–53
  • Khode S, Maddi V, Aragade P, et al. Synthesis and pharmacological evaluation of a novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines as novel anti-inflammatory and analgesic agents. Eur J Med Chem 2009;44:1682–8
  • Belluti F, Fontana G, Bo LD, et al. Design, synthesis and anticancer activities of stilbene-coumarin hybrid compounds: identification of novel proapoptotic agents. Bioorg Med Chem 2010;18:3543–50
  • Chimenti F, Bizzarri B, Bolasco A, et al. Synthesis and antihelicobacter pylori activity of 4-(coumarin-3-yl)thiazol-2-ylhydrazone derivatives. J Heterocycl Chem 2010;47:1269–74
  • Kostova I. Coumarins as inhibitors of HIV reverse transcriptase. Curr HIV Res 2006;4:347–63
  • Neyts J, Clercq DE, Singha R, et al. Structure-activity relationship of new anti-hepatitis C virus agents: heterobicycle-coumarin conjugates. J Med Chem 2009;52:1486–90
  • Ostrov DA, Prada JAH, Corsino PE, et al. Discovery of novel DNA gyrase inhibitors by high-throughput virtual screening. Antimicrob Agents Chemother 2007;51:3688–98
  • Roussaki M, Kontogiorgis CA, Litina DH, et al. A novel synthesis of 3-aryl coumarins and evaluation of their antioxidant and lipoxygenase inhibitory activity. Bioorg Med Chem Lett 2010;20:3889–92
  • Neelakantan S, Raman PV, Tinabaye A. A new and convenient synthesis of 4-methyl-3-phenylcoumarins and 3-phenylcoumarins. Indian J Chem Sect B 1982;21:256–57
  • Rescigno A, Sollai F, Pisu B, et al. Tyrosinase inhibition: general and applied aspects. J Enzyme Inhib Med Chem 2002;17:207–18
  • Reddy SAM, Mudgal J, Bansal P, et al. Antioxidant, anti-inflammatory and anti-hyperglycaemic activities of heterocyclic homoprostanoid derivatives. Bioorg Med Chem 2011;19:384–92
  • Abourashed EA, Mikell JR, Khan IA. Bioconversion of silybin to phase I and II microbial metabolites with retained antioxidant activity. Bioorg Med Chem 2012;20:2784–8
  • Seo WD, Ryu YB, Curtis-Long MJ, et al. Evaluation of anti-pigmentary effect of synthetic sulfonylamino chalcone. Eur J Med Chem 2010;45:2010–17
  • Saghaie L, Pourfarzam M, Fassihi A, Sartippour B. Synthesis and tyrosinase inhibitory properties of some novel derivatives of kojic acid. Res Pharm Sci 2013;8:233–42
  • Matoba Y, Kumagai T, Yamamoto A, et al. Crystallographic evidence that the dinuclear copper center of tyrosinase is flexible during catalysis. J Biol Chem 2006;281:8981–90
  • Chu W, Tu Z, McElveen E, et al. Synthesis and in vitro binding of N-phenyl piperazine analogs as potential dopamine D3 receptor ligands. Bioorg Med Chem 2005;13:77–87
  • Noh JM, Kwak SY, Seo HS, et al. Kojic acid-amino acid conjugates as tyrosinase inhibitors. Bioorg Med Chem Lett 2009;19:5586–9
  • Vilar S, Quezada E, Alcaide C, et al. Quantitative structure vasodilatory activity relationship. Synthesis and “in silico” and “in vitro” evaluation of resveratrol-coumarin hybrids. QSAR Comb Sci 2007;26:317–32

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