Synthesis of new glycyrrhetinic acid (GA) derivatives and their effects on tyrosinase activity

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 24, 2003, Pages 5345-5352

  Um, Soo Jong ^a   Park, Myoung Soon ^a   Park, Si Ho ^a   Han, Hye Sook ^a   Kwon, Youn Ja ^a   Sin, Hong Sig ^a  

^a Sejong University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

10 HYDROXY 2,4A,6A,6B,9,9,12A HEPTAMETHYL 1,2,3,4,4A,5,6,6A,6B,7,8,8A,9,10,11,12,12A,12B,13,14B EICOSAHYDROPICENE 2 CARBOXYLIC ACID [1 (PYRROLIDINE 2 CARBONYL)PIPERIDIN 4 YL]AMIDE; 10 HYDROXY 2,4A,6A,6B,9,9,12A HEPTAMETHYL 13 OXO 1,2,3,4,4A,5,6,6A,6B,7,8,8A,9,10,11,12,12A,12B,13,14B EICOSAHYDROPICENE 2 CARBOXYLIC ACID 4 FLUOROBENZYL ESTER; 10 HYDROXY 2,4A,6A,6B,9,9,12A HEPTAMETHYL 13 OXO 1,2,3,4,4A,5,6,6A,6B,7,8,8A,9,10,11,12,12A,12B,13,14B EICOSAHYDROPICENE 2 CARBOXYLIC ACID [1 (PYRROLIDINE 2 CARBONYL)PIPERIDIN 4 YL]AMIDE; 10 HYDROXY 2,4A,6A,6B,9,9,12A HEPTAMETHYL 13 OXO 1,2,3,4,4A,5,6,6A,6B,7,8,8A,9,10,11,12,12A,12B,13,14B, EICOSAHYDROPICENE 2 CARBOXYLIC ACID 4 FLUOROBENZYL ESTER; 10 HYDROXY 2,4A,6A,6B,9,9,12A, HEPTAMETHYL 1,2,3,4,4A,5,6,6A,6B,7,8,8A,9,10,11,12,12A,12B,13,14B EICOSAHYDROPICENE 2 CARBOXYLIC ACID 4 FLUOROBENZYL ESTER; 11 HYDROXYMETHYL 4,4,6A,6B,8A,11,14B HEPTAMETHYL 1,2,3,4,4A,5,6,6A,6B,7,8,8A,9,10,11,12,12A,14,14A,14B EICOSAHYDROPICEN 3 OL; ACETIC ACID 11 FORMYL 4,4,6A,6B,8A,11,14B HEPTAMETHYL 1,2,3,4,4A,5,6,6A,6B,7,8,8A,9,10,11,12,12A,14,14A,14B EICOSAHYDROPICEN 3 YL ESTER; ALCOHOL; ALDEHYDE; ASCORBIC ACID; BROMINE DERIVATIVE; CARBON 11; CARBOXYLIC ACID; ENZYME INHIBITOR; GLYCYRRHETINIC ACID DERIVATIVE; HYDROXY 2,4A,6A,6B,9,9,12A HEPTAMETHYL 1,2,3,4,4A,5,6,6A,6B,7,8,8A,9,10,11,12,12A,12B,13,14B EICOSAHYDROPICENE 2 CARBOXYLIC ACID; KETONE; KOJIC ACID; MONOPHENOL MONOOXYGENASE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; DRUG EFFECT; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INHIBITION; IC 50;

EID: 0345283017     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2003.09.046     Document Type: Article

References (28)

1. Finney R.S.H., Tarknoy A.L. J. Pharm. Pharmacol. 12:1960;49.
2. Pompei R., Flore O., Marcialis M.A., Pani A., Loddo B. Nature. 281:1979;689.
3. Tanaka S., Uno C., Akimoto M., Tabata M., Honda C., Kamisako W. Planta Med. 57:1991;527.
4. Nishino H., Kitagawa K., Iwashima A. Carcinogenesis. 5:1984;1529.
5. Yi H., Nakashima I., Isobe K. Am. J. Clin. Med. 24:1996;271.
6. Abe H., Ohya N., Yamamoto K.F., Shibuya T., Arichi S., Odashima S. Eur. J. Cancer Clin. Oncol. 23:1987;1549.
7. (a) Deckner G.E., SaNogueira J.P. Jr., Zukowski J.M. US Patent 5 968 528. 1999;
8. (b) Randall W.B., Prida C.L. US Patent. 1999;5 939 082.
9. Garcia-Borron J.C., Solano F. Pigment Cell Res. 15:2002;162.
10. Riley P.A. Pigment Cell Res. 6:1993;182.
11. Hansson C., Rorsman H., Rosengren E. Acta Derm. Venereol. 61:1981;147.
12. Cabanes J., Chazarra S., Garcia-Carmona F. J. Pharm. Pharmacol. 46:1994;982.
13. Morisaki K., Ozaki S. Chem. Pharm. Bull. (Tokyo). 44:1996;1647.
14. (a) Chung Y.J., Kim Y.-C., Park H.-J. Bull. Kor. Chem. Soc. 23:2002;1481
15. (b) den Branden S.V., Compernolle F., Hoornaert G.J. J. Chem. Soc., Perkin Trans. 1. 1992;1035.
16. Sin H.S., Kwon Y.J., Han H.S., Park S.H., Park M.S., Rho Y.S., Um S.J. Bull. Kor. Chem. Soc. 23:2002;1806.
17. Saito S., Nagase S., Kawase M., Nagamura Y. Eur. J. Med. Chem. 31:1996;557.
18. Tierney M.T., Grinstaff M.W. J. Org. Chem. 65:2000;5355.
19. Saari W.S., Schwering J.E., Lyle P.A., Smith S.J., Engelhardt E.L. J. Med. Chem. 33:1990;97.
20. Takahashi K., Shibata S., Yano S., Harada M., Saito H., Tamura Y., Kumagai A. Chem. Pharm. Bull. 28:1980;3449.
21. Gopinath R., Patel B.K. Org. Lett. 2:2000;4177.
22. Fürstner A., Mlynarski J., Albert M. J. Am. Chem. Soc. 124:2002;10274.
23. Abiko A., Roberts J.C., Takemasa T., Masamune S. Tetrahedron Lett. 27:1986;4537.
24. Morrison J.E. Trends Biochem. Sci. 7:1982;102.
25. Cabanes J., Garcia-Carmona F., Garcia-Canovas F., Iborra J.L., Lozano J.A. Biochim. Biophys. Acta. 790:1984;101.
26. Cabanes J., Garcia-Canovas F., Tudela J., Lozano J.A., Garciaa-Carmona F. Phytochemistry. 26:1987;917.
27. Jung G.D., Yang J.Y., Song E.S., Park J.W. Exp. Mol. Med. 33:2001;131.
28. Yokota T., Nishio H., Kubota Y., Mizoguchi M. Pigment Cell Res. 11:1998;355.