Syntheses of hydroxy substituted 2-phenyl-naphthalenes as inhibitors of tyrosinase

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 2, 2007, Pages 461-464

  Song, Suhee ^a   Lee, Hyojin ^a   Jin, Youngeup ^a   Ha, Young Mi ^a   Bae, Sungjin ^a   Chung, Hae Young ^a   Suh, Hongsuk ^a  

^a Pusan National University   (South Korea)

Author keywords

Oxyresveratrol; Resveratrol; Tyrosinase; X ray structure

Indexed keywords

4 (6 HYDROXY 2 NAPHTHYL) 1,3 BENZENEDIOL; 5 (6 HYDROXY 2 NAPHTHYL) 1,3 BENZENEDIOL; 7 (3,5 DIHYDROXYPHENYL) 1,3 NAPHTHALENEDIOL; ADENOSINE TRIPHOSPHATASE; MONOPHENOL MONOOXYGENASE; NAPHTHALENE DERIVATIVE; OXYRESVERATROL; PROSTAGLANDIN SYNTHASE; RESVERATROL; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; IC 50; LIVER MITOCHONDRION; MUSHROOM; NONHUMAN; RAT;

AGARICALES; CRYSTALLOGRAPHY, X-RAY; DEALKYLATION; ENZYME INHIBITORS; HYDROQUINONES; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MODELS, MOLECULAR; MONOPHENOL MONOOXYGENASE; MORUS; NAPHTHALENES; PYRONES; STILBENES;

BASIDIOMYCOTA; RATTUS;

EID: 33846070701     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.10.025     Document Type: Article

References (31)

1. Qiu F., Komtasu K.I., Saito K.I., Kawasaki K., Yao X., and Kano Y. Biol. Pharm. Bull. 19 (1996) 1463
2. Kim Y.M., Yun J., Lee C.K., Lee H., Min K.R., and Kim Y. J. Biol. Chem. 277 (2002) 16340
3. Katsuki, O. Jpn Patent 6,256,150, 1994.
4. Shin N.H., Ryu S.Y., Choi E.J., Kang S.H., Chang I.M., Min K.R., and Kim Y. Biochem. Biophys. Res. Commun. 243 (1998) 801
5. Shin N.H., Ryu S.Y., Lee H.S., Min K.R., and Kim Y.S. Planta Med. 64 (1998) 283
6. Nimmanpisut S., Chudapongse P., and Ratanabanangkoon K. Biochem. Pharmacol. 25 (1976) 1248
7. Riley P. J. Theor. Biol. 203 (2000) 1
8. Palumbo A., d'Ischia M., Misuraca G., and Prota G. Biochem. Biophys. Acta 1073 (1991) 85
9. Smit N., Vicanova J., Cramers P., Vrolijk H., and Paverl S. Skin Pharmacol. Physiol. 17 (2004) 238
10. Lim J.T. Dermatol. Surg. 25 (1999) 292
11. Maeda K., and Fukuda M. J. Pharmacol. Exp. Ther. 276 (1996) 765
12. Ohguchi K., Tanaka T., Ito T., Iinuma M., Matsumoto K., Akao Y., and Nozawa Y. Biosci. Biotechnol. Biochem. 67 (2003) 1587
13. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 615494. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (0)1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
14. 4 300.1362).
15. 6) δ 55.3, 55.4, 55.6, 98.2, 99.6, 104.2, 106.7, 118.7, 125.8, 129.0, 130.9, 139.6, 158.3, 160.4, 160.5.
16. 4 324.1362).
17. 4 268.0736).
18. 3 294.1256).
19. 4 324.1362).
20. 2 264.1150).
21. 3 294.1256).
22. 3 252.0786).
23. 4 268.0736).
24. 2 236.0837).
25. 3 252.0786).
26. Li X.M., Hung K.S., Lin M., and Zhou L.X. Tetrahedron 59 (2003) 4405
27. Gerber N.N. Phytochemistry 25 (1986) 1697
28. Minutolo F., Sala G., Bagnacani A., Bertini S., Carboni I., Placanica G., Prota G., Rapposelli S., Sacchi N., Macchia M., and Ghiconi R. J. Med. Chem. 48 (2005) 6783
29. Roberti M., Pizzirani D., Recanatini M., Simoni D., Grimaudo S., Antonietta D.C., Abbadessa V., Gebbia N., and Tolomeo M. J. Med. Chem. 49 (2006) 3012
30. Mewshaw R.E., Edsall R.J., Yang C., Manas E.S., Xu Z.B., Henderson R.A., Keith J.C., and Harris H.A. J. Med. Chem. 48 (2005) 3953
31. 492) in a microplate leader (Hewlett-Packard).