Synthesis and anti-hepatitis B virus evaluation of novel ethyl 6-hydroxyquinoline-3-carboxylates in vitro

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 13, 2008, Pages 6522-6527

  Liu, Yajing ^a   Zhao, Yanfang ^a   Zhai, Xin ^a   Feng, Xusheng ^a   Wang, Jinxin ^a   Gong, Ping ^a  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Ethyl 6 hydroxyquinoline 3 carboxylates; Hepatitis B virus; HepG2.2.15 cells; Synthesis

Indexed keywords

5 HYDROXY 1H INDOLE 2 CARBOXYLATE DERIVATIVE; 6 HYDROXYQUINOLINE 3 CARBOXYLATE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ETHYL 2 [(2 METHOXYPHENYLTHIO)METHYL] 5 [(DIMETHYLAMINO)METHYL] 6 HYDROXY 7 METHOXYQUINOLINE 3 CARBOXYLIC ACID; ETHYL 2 [(3,3 DIFLUOROPHENYLTHIO)METHYL] 6 HYDROXY 7 METHOXY 5 (MORPHOLINOMETHYL)QUINOLINE 3 CARBOXYLIC ACID; ETHYL 2 [(3,4 DIFLUOROPHENYLSULFINYL)METHYL] 6 HYDROXY 7 METHOXY 5 [(PYRROLIDIN 1 YL)METHYL]QUINOLINE 3 CARBOXYLIC ACID; ETHYL 2 [(3,4 DIFLUOROPHENYLTHIO)METHYL] 6 HYDROXY 7 METHOXY 5 [(4 METHYLPIPERAZIN 1 YL)METHYL]QUINOLINE 3 CARBOXYLIC ACID; ETHYL 2 [(3,4 DIFLUOROPHENYLTHIO)METHYL] 6 HYDROXY 7 METHOXY 5 [(PIPERIDIN 1 YL)METHYL]QUINOLINE 3 CARBOXYLIC ACID; ETHYL 2 [(4 FLUOROPHENYLSULFINYL)METHYL] 5 [(DIMETHYLAMINO)EMINO] 6 HYDROXY 7 METHOXYQUINOLINE 3 CARBOXYLIC ACID; ETHYL 2 [(4 FLUOROPHENYLSULFINYL)METHYL] 6 HYDROXY 7 METHOXY 5 [(PYRROLIDIN 1 YL)METHYL]QUINOLINE 3 CARBOXYLIC ACID; ETHYL 2 [(4 FLUOROPHENYLTHIO)METHYL] 5 [(DIMETHYLAMINO)METHYL] 6 HYDROXY 7 METHOXYQUINOLINE 3 CARBOXYLIC ACID; ETHYL 2 [(4 FLUOROPHENYLTHIO)METHYL] 6 HYDROXY 7 METHOXY 5 (2 METHYL 1H IMIDAZOL 1 YL)QUINOLINE 3 CARBOXYLIC ACID; ETHYL 2 [(4 FLUOROPHENYLTHIO)METHYL] 6 HYDROXY 7 METHOXY 5 [(PYRROLIDIN 1 YL)METHYL]QUINOLINE 3 CARBOXYLIC ACID; ETHYL 5 [(1H IMIDAZOLE 1 YL)METHYL] 2 [(3 METHOXYPHENYLSULFINYL)METHYL] 6 HYDROXY 7 METHOXYQUINOLINE 3 CARBOXYLIC ACID; ETHYL 5 [(1H IMIDAZOLE 1 YL)METHYL] 2 [(3 METHOXYPHENYLTHIO)METHYL] 6 HYDROXY 7 METHOXYQUINOLINE 3 CARBOXYLIC ACID; ETHYL 5 [(1H IMIDAZOLE 1 YL)METHYL] 2 [(3,4 DIFLUOROPHENYLSULFINYL)METHYL] 6 HYDROXY 7 METHOXYQUINOLINE 3 CARBOXYLIC ACID; ETHYL 5 [(1H IMIDAZOLE 1 YL)METHYL] 2 [(3,4 DIFLUOROPHENYLTHIO)METHYL] 6 HYDROXY 7 METHOXYQUINOLINE 3 CARBOXYLIC ACID; ETHYL 5 [(1H IMIDAZOLE 1 YL)METHYL] 2 [(3,4 DIMETHOXYPHENYLTHIO)METHYL] 6 HYDROXY 7 METHOXYQUINOLINE 3 CARBOXYLIC ACID; ETHYL 5 [(1H IMIDAZOLE 1 YL)METHYL] 2 [(4 FLUOROPHENYLSULFINYL)METHYL] 6 HYDROXY 7 METHOXYQUINOLINE 3 CARBOXYLIC ACID; ETHYL 5 [(1H IMIDAZOLE 1 YL)METHYL] 2 [(4 FLUOROPHENYLTHIO)METHYL] 6 HYDROXY 7 METHOXYQUINOLINE 3 CARBOXYLIC ACID; ETHYL 6 HYDROXY 7 METHOXY 2 [(PHENYLTHIO)METHYL] 5 [(PIPERIDIN 1 YL)METHYL]QUINOLINE 3 CARBOXYLIC ACID; ETHYL 6 HYDROXY 7 METHOXY 2 [(PYRIDIN 2 YLSULFINYL)METHYL] 5 [(PYRROLIDIN 1 YL)METHYL]QUINOLINE 3 CARBOXYLIC ACID; ETHYL 6 HYDROXY 7 METHOXY 2 [(PYRIDIN 2 YLTHIO)METHYL] 5 [(PYRROLIDIN 1 YL)METHYL]QUINOLINE 3 CARBOXYLIC ACID; ETHYL 6 HYDROXYQUINOLINE 3 CARBOXYLATE DERIVATIVE; HEPATITIS B ANTIBODY; HEPATITIS B SURFACE ANTIGEN; HEPATITIS B(E) ANTIGEN; LAMIVUDINE;

ANTIGEN EXPRESSION; ANTIVIRAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY; DNA REPLICATION; DRUG STRUCTURE; DRUG SYNTHESIS; HEPATITIS B VIRUS; HUMAN; HUMAN CELL; IN VITRO STUDY; LIVER CELL; MANNICH REACTION; STRUCTURE ACTIVITY RELATION; VIRUS REPLICATION;

ANTIVIRAL AGENTS; CELL LINE, TUMOR; HEPATITIS B VIRUS; HUMANS; HYDROXYQUINOLINES; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

HEPATITIS B VIRUS;

EID: 44849136274     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.05.029     Document Type: Article

References (15)

1. Custer B., Sullivan S.D., Hazlet T.K., Iloeje U., Veenstra D.L., and Kowdley K.V. J. Clin. Gastroenterol. 38 (2004) S158
2. Fattovich G., Brollo L., Alberti A., Pontisso P., Giustina G., and Realdi G. Hepatology 8 (1988) 1651
3. Fischer K.P., Gutfreund K.S., and Tyrrell D.L. Drug Resist. Updat. 4 (2001) 98
4. Danta M., and Dusheiko G. Int. J. Clin. Practice 58 (2004) 877
5. Colonno R.J., Rose R., Baldick C.J., Levine S., Podornowski K., Yu C.F., Walsh A., Fang J., Hsu M., Mazzucco C., Eggers B., Zhang S., Plym M., Klesczewski K., and Tenney D.J. Hepatology 44 (2006) 1656
6. Sims K.A., and Woodland A.M. Pharmacotherapy 26 (2006) 1745
7. Chai H.F., Zhao Y.F., Zhao C.S., and Gong P. Bioorg. Med. Chem. 14 (2006) 911
8. Zhao C.S., Zhao Y.F., Chai H.F., and Gong P. Bioorg. Med. Chem. 14 (2006) 2552
9. Sumiaki K., Hirofumi T., Tetsuya K., Kiyoharu N., and Manabu N. Tetrahedron 60 (2004) 4901
10. Patteux C., Foucout L., Bohn P., Dupas G., Leprince J., Tonon M.C., Dehouck B., Marsais F., Papamicael C., and Levacher V. Org. Biomol. Chem. 4 (2006) 817
11. Friedländer P., and Gohring C.F. Ber. Dtsch. Chem. Ges. 16 (1883) 1833
12. -1) 3437 (OH), 1710 (C{double bond, long}O).
13. Korba B.E., and Milman G. Antiviral Res. 15 (1991) 217
14. Sells M.A., Zelent A.Z., Shvartsan M., and Acs G. Biochem. Biophys. Res. Commun. 156 (1988) 1144
15. Mosmann T. J. Immunol. Methods 65 (1983) 55