Synthesis of 4-hydroxycoumarin and 2,4-quinolinediol derivatives and evaluation of their effects on the viability of HepG2 cells and human hepatocytes culture

European Journal of Medicinal Chemistry

Volumn 39, Issue 11, 2004, Pages 931-937

  Refouvelet, Bernard ^a   Guyon, Catherine ^a   Jacquot, Yves ^a   Girard, Corinne ^a   Fein, Hervé ^a   Bévalot, Françoise ^a   Robert, Jean François ^a   Heyd, Bruno ^b   Mantion, Georges ^b   Richert, Lysiane ^a   Xicluna, Alain ^a  

^a UNIVERSITÉ DE FRANCHE COMTÉ   (France)

^b UNIVERSITY HOSPITAL JEAN MINJOZ   (France)

Author keywords

Cell viability; Coumarins; Human liver cells; Quinolones

Indexed keywords

2,4 DIHYDRO 1 METHYL 3 BENZYLIDENEQUINOLIN 2,4 DIONE; 2,4 DIHYDRO 3 (4 METHOXYBENZYLIDENE)BENZOPYRAN 2,4 DIONE; 2,4 DIHYDRO 3 BENZYLIDENEBENZOPYRAN 2,4 DIONE; 2,4 DIHYDRO 3 BENZYLIDENEQUINOLIN 2,4 DIONE; 4 HYDROXYCOUMARIN DERIVATIVE; 5 METHYL 6,12 DIHYDROQUINOLO[3,4 B][1,4]BENZOTHIAZIN 6 ONE; 6,12 DIHYDRO 3 METHOXYBENZOPYRANO[3,4 B][1,4]BENZOTHIAZIN 6 ONE; 6,12 DIHYDROBENZOPYRANO[3,4 B][1,4]BENZOTHIAZIN 6 ONE; 6,12 DIHYDROQUINOLO[3,4 B][1,4]BENZOTHIAZIN 6 ONE; BENZOPYRAN DERIVATIVE; BENZOPYRONE; BENZYLIDENE DERIVATIVE; HETEROCYCLIC COMPOUND; NITROGEN; QUINOLINE DERIVATIVE; QUINOLONE; SULFUR; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CELL DEATH; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG EFFECT; DRUG SCREENING; DRUG SYNTHESIS; HEPATOMA CELL; HUMAN; HUMAN CELL; LIVER CELL CULTURE; LIVER PROTECTION; OXIDATIVE STRESS;

4-HYDROXYCOUMARINS; CARCINOMA, HEPATOCELLULAR; CELL SURVIVAL; CELLS, CULTURED; HEPATOCYTES; HUMANS; LIVER NEOPLASMS; OXIDATIVE STRESS; PROTECTIVE AGENTS; QUINOLINES; TERT-BUTYLHYDROPEROXIDE;

EID: 6344291379     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejmech.2004.07.006     Document Type: Article

References (37)

1. Micheli R.A., Booth A.N., Livingston A.L., and Bickoff E.M. J. Med. Chem. 5 1962 321 329
2. Nishimura S., Taki M., Takaishi S., Lijima Y., and Akiyama T. Chem. Pharm. Bull. 48 2000 505 508
3. Jacquot Y., Bermont L., Giorgi H., Refouvelet B., Adessi G.L., Daubrosse E., and Xicluna A. Eur. J. Med. Chem. 36 2001 127 136
4. Cao S.-G., Wu X.-H., Sim K.-Y., Tan B.H.K., Vittal J.J., Pereira J.T., and Goh S.-H. Helv. Chim. Acta 81 1998 1404 1407
5. Fujioka T., Furumi K., Fujii H., Okabe H., Mihashi K., Nakano Y., Matsunaga H., Katano M., and Mori M. Chem. Pharm. Bull 47 1999 96 100
6. Woo L.W.L., Purohit A., Malini B., Reed M.J., and Potter B.V.L. Chem. Biol. 7 2000 773 791
7. Purohit A., Woo L.W.L., Barrox D., Hejaz H.A.M., Nicholson R.I., Potter B.V.L., and Reed M.J. Mol. Cell. Endocrinol. 171 2001 129 135
8. Jacquot Y., Cleeren A., Laios J., Ma Y., Boulahdour A., Bermont L., Refouvelet B., Adessi G., Leclercq G., and Xicluna A. Biol. Pharm. Bull. 25 2002 335 341
9. Jacquot Y., Refouvelet B., Bermont L., Adessi G.L., Leclercq G., and Xicluna A. Pharmazie 57 2002 233 237
10. Iannone A., Bini A., Jin G., Vannini V., and Tomasi A. Free Radical Res. Comm. 19 1993 141 147
11. Sies H., and Summer K.H.H. Eur. J. Biochem. 57 1975 503 512
12. Nicod L., Viollon C., Regnier A., Jacqueson A., and Richert L. Hum. Exp. Toxicol. 16 1997 28 34
13. Alexandre E., David P., Viollon-Abadie C., Azimzadeh A., Wolf P., Jaeck D., Nicod L., Boudjema K., and Richert L. Toxicol. In Vitro 13 1999 427 435
14. Goll V., Viollon-Abadie C., Nicod L., and Richert L. Hum. Exp. Toxicol. 19 2000 193 202
15. Colombain M., Goll V., Muyard F., Girard C., Bévalot F., and Richert L. Planta Med. 67 2001 644 646
16. Gore M.A., Morshedi M.M., and Reidhaar-Olson J.F. Funct. Integ. Genomics 1 2000 114 126
17. Yamamoto Y., Bnakajima M., Yamazaki H., and Yokoi T. Life Sci. 70 2001 471 482
18. Carubbi F., Guicciardi M.E., Concazri M., Loria P., Bertolotti M., and Carilli N. Bicochem. Biophys. Acta 1580 2002 31 39
19. Martin K.R., Failla M.L., and Smith J.C. J. Nutr. 126 1996 2098 2106
20. Kim J.A., Kang Y.S., Lee S.H., and Lee Y.S. Free Radical Res. 33 2000 267 277
21. Feg Q., Torii Y., Uchda K., Nakamura Y., Hara Y., and Osawa T. J. Agric. Food Chem. 2 2002 213 220
22. Jayashree A., Rao V.S., and Darbarwar M. Synth. Commun. 20 7 1990 919 924
23. Buu-Ho N.P., Mangane M., and Jacquignon P. J. Chem. Soc. (C) 1966 50 52
24. Vanhaelen M., and Vanhaelen-Fastré R. Pharm. Acta Helv. 51 1976 307 312
25. Tabakovic K., Tabakovic I., Trkovnik M., Juric A., and Trinajstic N. J. Heterocyclic Chem. 17 1980 801 803
26. Reddy B.S., and Darbarwar M. J. Indian Chem. Soc. 62 1985 377 379
27. Maurel P. Drug Delivery Rev. 22 1996 105 132
28. David P., Viollon-Abadie C., Alexandre E., Nicod L., Wolf P., Jeack D., Boudjema K., and Richert L. Hum. Exp. Toxicol. 17 1998 544 553
29. Goll V., Alexandre E., Viollon-Abadie C., Nicod L., Jaeck D., and Richert L. Toxicol. Appl. Pharmacol. 160 1999 21 32
30. Da Settimo A., Marini A.-M., Primofiore G., Da Settimo F., Salerno S., La Mota C., Pardit G., Ferrarini P.L., and Mori C. J. Heterocyclic Chem. 37 2000 379 382
31. Davey W., and Gwilt J.E. J. Chem. Soc. 1957 1008 1019
32. Clement A.M., and Chipman J.K. Carcinogenesis 19 9 1998 1583 1589
33. Wang H., and Joseph J.A. Free Radical Biol. Med. 27 5and 6 1999 683 694
34. Sugihara N., Arakawa T., Onhnishi M., and Furuno K. Free Radical Biol. Med. 27 11and 12 1999 1313 1323
35. Nagata H., Takekoshi S., Takagi T., Honma T., and Watanabe K. J. Tokai, Exp. Clin. Med. 24 1 1999 1 11
36. Richert L., Binda D., Hamilton G., Viollon-Abadie C., Alexandre E., Bigot-Lasserre D., Bars R., Cassolo P., and LeCluyse E. Toxicol. In Vitro 16 2002 89 99
37. Carmichael J., DeGraff W.G., Gazdar A.F., Minna J.D., and Mitchell J.B. Cancer Res. 47 1987 936 942