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4-Hydroxy-2'-Nitrodiphenyl Ether Analogues as Novel Tyrosinase Inhibitors

  • Received : 2010.02.16
  • Accepted : 2010.03.17
  • Published : 2010.05.20

Abstract

Tyrosinase ubiquitously existing from microorganisms to animals and plants is known to be the most critical and rate limiting enzyme during melanin biosynthesis. In order to develop new tyrosinase inhibitor we have synthesized 14 diphenyl ether compounds possessing hydroxyl, bromo, and nitro groups in the structure. Among the compounds prepared, 18 and 19 have shown much stronger inhibition of tyrosinase monophenolase function than arbutin used as a positive control. Both compounds 18 and 19 possess para-hydroxyphenyl moiety in their structure, which might reinforce the importance of p-hydroxyphenyl group in the tyrosinase inhibitory process. In the DPPH radical scavenging activity test, none of the compounds even 18 and 19 showed significant antioxidant activity. The results suggest that elaborate adjustment of diphenyl ether analogues with proper substituents have potential to be developed as new skin whitening agents working on the tyrosinase function.

Keywords

References

  1. Schallreuter, K. U.; Kothari, S.; Chavan, B.; Spencer, J. D. Exp. Dermatol. 2007, 17, 395. https://doi.org/10.1111/j.1600-0625.2007.00675.x
  2. Parvez, S.; Kang, M.; Chung, H. S.; Bae, H. Phytother. Res. 2007, 21, 805. https://doi.org/10.1002/ptr.2184
  3. Criton, M.; Le Mellay-Hamon, V. Bioorg. Med. Chem. Lett. 2008, 12, 3607.
  4. Hearing, V. J.; Tsukamoto, K. FASEB. J. 1991, 5, 2902. https://doi.org/10.1096/fasebj.5.14.1752358
  5. Likhitwitayawuid, K. Curr. Sci. 2008, 94, 44.
  6. Kim, Y. J.; No, J. K.; Lee, J. H.; Chung, H. A. Biol. Pharm. Bull. 2005, 28, 323. https://doi.org/10.1248/bpb.28.323
  7. Solano, F.; Briganti, S.; Picardo, M.; Ghanem, G. Pigment Cell Res. 2006, 19, 550. https://doi.org/10.1111/j.1600-0749.2006.00334.x
  8. Menter, J. M.; Etemadi, A. A.; Chapman, W.; Hollins, T. D.; Willis, I. Melanoma Res. 1993, 3, 443. https://doi.org/10.1097/00008390-199311000-00007
  9. Khatib, S.; Nerya, O.; Musa, R.; Shmuel, M.; Tamir, S.; Vaya, J. Bioorg. Med. Chem. 2005, 13, 433. https://doi.org/10.1016/j.bmc.2004.10.010
  10. Passi, S.; Nazzaro-Porro, M. Br. J. Dermatol. 1981, 104, 659. https://doi.org/10.1111/j.1365-2133.1981.tb00752.x
  11. Briganti, S.; Camera, E.; Picardo, M. Pigment Cell Res. 2003, 16, 101. https://doi.org/10.1034/j.1600-0749.2003.00029.x
  12. Ohyama, Y.; Mishima, Y. Fragrance J. 1990, 6, 53.
  13. Tokiwa, Y.; Kitagawa, M.; Raku, T.; Yanagitani, S.; Yoshino, K. Biorg. Med. Chem. Lett. 2007, 17, 3105. https://doi.org/10.1016/j.bmcl.2007.03.039
  14. Hori, I.; Nihei, K.-I.; Kubo, I. Phytother. Res. 2004, 18, 475. https://doi.org/10.1002/ptr.1456
  15. Oozeki, H.; Tajima, R.; Nihei, K.-i. Bioorg. Med. Chem. Lett. 2008, 18, 5252. https://doi.org/10.1016/j.bmcl.2008.08.053
  16. Chomcheon, P.; Wiyakrutta, S.; Sriubolmas, N.; Ngamrojanavanich, N.; Kengtong, S.; Mahidol, C.; Ruchirawat, S.; Kittakoop, P. Phytochem. 2009, 70, 407. https://doi.org/10.1016/j.phytochem.2009.01.007
  17. Marcoux, J.-F.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539. https://doi.org/10.1021/ja971901j
  18. Xu, H.; Jian, K.-Z.; Guan, Q.; Ye, F.; Lv, M. Chem. Pharm. Bull. 2007, 55, 1755. https://doi.org/10.1248/cpb.55.1755
  19. Li, K.; Li, X.-M.; Ji, N.-Y.; Wang, B.-G. Bioorg. Med. Chem. 2007, 15, 6627. https://doi.org/10.1016/j.bmc.2007.08.023
  20. de la Fuente, J. A.; Manzanaro, S.; Martin, M. J.; de Quesada, T. G.; Reymundo, I.; Leungo, S. M.; Gago, F. J. Med. Chem. 2003, 46, 5208. https://doi.org/10.1021/jm030957n
  21. Masamoto, Y.; Ando, H.; Murata, Y.; Shimoishi, Y.; Tada, M.; Tanahata, K. Biosci. Biotechnol. Biochem. 2003, 67, 631. https://doi.org/10.1271/bbb.67.631
  22. Kim, B.-T.; O, K.-J.; Chun, J.-C.; Hwang, K.-J. Bull. Korean Chem. Soc. 2008, 29, 1125. https://doi.org/10.5012/bkcs.2008.29.6.1125

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  1. ChemInform Abstract: 4‐Hydroxy‐2′‐nitrodiphenyl Ether Analogues as Novel Tyrosinase Inhibitors. vol.41, pp.40, 2010, https://doi.org/10.1002/chin.201040068
  2. Synthesis and anti-melanogenic activity of hydroxyphenyl benzyl ether analogues vol.19, pp.7, 2010, https://doi.org/10.1016/j.bmc.2011.02.044