Synthesis and the biological evaluation of arylnaphthalene lignans as anti-hepatitis B virus agents

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 3, 2010, Pages 1213-1226

  Janmanchi, Damodar ^a,b   Tseng, Ya Ping ^a   Wang, Kuei Chen ^a   Huang, Ray Ling ^c   Lin, Chih Hsiu ^b   Yeh, Sheau Farn ^a  

^a NATIONAL YANG MING UNIVERSITY   (Taiwan)

^b INSTITUTE OF CHEMISTRY   (Taiwan)

^c MEIHO UNIVERSITY   (Taiwan)

Author keywords

Anti HBV; Helioxanthin derivatives; Hepatitis B virus

Indexed keywords

10 (3 BENZYLOXY 4 METHOXYPHENYL)FURO[3',4':6,7] NAPHTHO[1,2 D][1,3]DIOXOL 7,9 DIONE; 10 (3 HYDROXY 4 METHOXYPHENYL) 9H FURO[3',4':6,7] NAPHTHO[1,2D][1,3]DIOXOL 7 ONE; 10 (4 TRIFLUOROMETHOXYPHENYL) 9H FURO[3',4':6,7] NAPHTHO[1,2 D][1,3]DIOXOL 7 ONE; 10 (6 BROMOBENZO[1,3]DIOXOL 5 YL) 7 OXO 7,9 DIHYDROFURO[3',4':6,7]NAPHTHA[1,2 D][1,3]DIOXOLE 5 CARBONITRILE; 10 BENZO[1,3]DIOXOL 5 YL 5 BROMO 9H FURO[3',4':6,7]NAPHTHO [1,2 D][1,3]DIOXOL 7 ONE; 10 BENZO[1,3]DIOXOL 5 YL 7 OXO 7,9 DIHYDROFURO [3',4':6,7]NAPHTHO[1,2 D][1,3]DIOXOLE 5 CARBONITRILE; 10 BENZO[1,3]DIOXOL 5 YL 8 (2 HYDROXYETHYL) 1,3 DIOXA 8 AZA DICYCLOPENTA[A,G]NAPHTHALENE 7,9 DIONE; 4 BENZO[1,3]DIOXOL 5 YL 3H NAPHTHO[2,3 C]FURAN 1,5,6 TRIONE; 5 BROMO 10 (6 BROMO BENZO[1,3]DIOXOL 5 YL) 9H FURO [3',4':6,7]NAPHTHA[1,2 D][1,3]DIOXOL 7 ONE; 9 BENZO[1,3]DIOXOL 5 YL 6 HYDROXYNAPHTHO[1,2 D][1,3]DIOXOLE 7,8 DICARBAXYLIC ACID 8 METHYL ESTER; 9 BENZO[1,3]DIOXOL 5 YL 6 HYDROXYNAPHTHO[1,2 D][1,3]DIOXOLE 7,8 DICARBAXYLIC ACID DIMETHYL ESTER; 9 BENZO[1,3]DIOXOL 5 YL 6 METHOXYNAPHTHO[1,2 D][1,3]DIOXOL 7,8 DICARBAXYLIC ACID 8 METHYL ESTER; 9 BENZO[1,3]DIOXOL 5 YL 6 METHOXYNAPHTHO[1,2 D][1,3]DIOXOLE 7,8 DICARBAXYLIC ACID DIMETHYL ESTER; 9 BENZO[1,3]DIOXOL 5 YL 7,8 BIS BROMOMETHYLNAPHTHO[1,2 D][1,3]DIOXOLE; 9 BENZO[1,3]DIOXOL 5 YL 8 HYDROXYMETHYL NAPHTHO[1,2 D][1,3] DIOXOLE 7 CARBOXYLIC ACID MONOSODIUM SALT; 9 BENZO[1,3]DIOXOL 5 YL NAPHTHO[1,2 D][1,3]DIOXOLE 7,8 DICARBALDEHYDE; 9 BENZO[1,3]DIOXOL 5 YL NAPHTHO[1,2 D][1,3]DIOXOLE 7,8 DICARBAXYLIC ACID DIETHYL ESTER; [9 BENZO[1,3]DIOXOL 5 YL 7 DIHYDROXMETHYLNAPHTHO[1,2 D][1,3]DIOXOL 8 YL] METHANOL; ACETIC ACID 2 (10 BENZO[1,3]DIOXOL 5 YL 7,9 DIOXO 7,9 DIHYDRO 1,3 DIOXA 8 AZA DICYCLOPENTA[A,G]NAPHTHALENE 8 YL) ETHYL ESTER; ACETIC ACID 8 ACETOXYMETHYL 9 BENZO[1,3]DIOXOL 5 YLNAPHTHO[1,2 D][1,3]DIOXOL 7 YL METHY ESTER; ACETIC ACID 9 BENZO[1,3]DIOXOL 5 YL 8 FORMYLNAPHTHO[1,2 D][1,3]DIOXOL 7 YL METHYL ESTER; ACETIC ACID 9 BENZO[1,3]DIOXOL 5 YL 8 HYDROXMETHYLNAPHTHO[1,2 D][1,3]DIOXOL 7 YL METHYESTER; ANTIVIRUS AGENT; HELIOXANTHIN DERIVATIVE; LAMIVUDINE; LIGNAN DERIVATIVE; MEMBRANE ANTIGEN; MESSENGER RNA; UNCLASSIFIED DRUG; UNINDEXED DRUG; VIRUS DNA;

ANTIVIRAL ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL STRAIN HEPA2; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG MECHANISM; DRUG SCREENING; DRUG SYNTHESIS; HEPATITIS B; HEPATITIS B VIRUS; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION; VIRUS REPLICATION; VIRUS STRAIN; WILD TYPE;

CELL LINE, TUMOR; HEPATITIS B; HEPATITIS B E ANTIGENS; HEPATITIS B SURFACE ANTIGENS; HEPATITIS B VIRUS; HUMANS; LIGNANS; PROMOTER REGIONS, GENETIC; STRUCTURE-ACTIVITY RELATIONSHIP; VIRAL CORE PROTEINS; VIRUS REPLICATION;

HEPATITIS B VIRUS;

EID: 75149177191     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.12.038     Document Type: Article

References (32)

1. Chang M.H., Chen C.J., Lai M.S., Hsu H.M., Wu T.C., Kong M.S., Liang D.C., Shau W.Y., and Chen D.S. N. Eng. J. Med. 336 (1997) 1855
2. Robinson W.S. Annu. Rev. Microbiol. 31 (1977) 357
3. Yuh C.H., and Ting L.P. J. Virol. 64 (1990) 4281
4. Dienstag J.L., Perrillo R.P., Schiff E.R., Bartholomew M., Vicary C., and Rubin M. N. Eng. J. Med. 333 (1995) 1657
5. Walsh K.M., Woodall T., Lamy P., Wight D.G., Bloor S., and Alexander G.J. Gut 49 (2001) 436
6. Franco J., and Saeian K. J. Vasc. Interv. Radiol. 13 (2002) S191
7. Langley D.R., Walsh A.W., Baldick C.J., Eggers B.J., Rose R.E., Levine S.M., Kapur A.J., Colonno R.J., and Tenney D.J. J. Virol. 81 (2007) 3992
8. Ruiz-Sancho A., Sheldon J., and Soriano V. Expert Opin. Biol. Ther. 7 (2007) 751
9. Lee H.S., Chung Y.H., Lee K.S., Byun K.S., Paik S.W., Han J.Y., Yoo K., Yoo H.W., Lee J.H., and Yoo B.C. Hepatology 43 (2006) 982
10. Zoulim F. J. Clin. Virol. 21 (2001) 243
11. Yeh C.T., Chien R.N., Chu C.M., and Liaw Y.F. Hepatology 31 (2000) 1318
12. Locarnini S., and Mason W.S. J. Hepatol. 44 (2006) 422
13. Mohanty S.R., Kupfer S.S., and Khiani V. Nat. Clin. Pract. Gastroenterol. Hepatol. 3 (2006) 446
14. Lee Y.S., Suh D.J., Lim Y.S., Jung S.W., Kim K.M., Lee H.C., Chung Y.H., Yoo W., and Kim S.O. Hepatology 43 (2006) 1385
15. Deres K., Schroder C.H., Paessens A., Goldmann S., Hacker H.J., Weber O., Kramer T., Niewohner U., Pleiss U., Stoltefuss J., Graef E., Koletzki D., Masantschek R.N., Reimann A., Jaeger R., Gross R., Beckermann B., Schlemmer K.H., Haebich D., and Rubsamen-Waigmann H. Science 299 (2003) 893
16. Tan T.M., Chen Y., Kong K.H., Bai J., Li Y., Lim S.G., Ang T.H., and Lam Y. Antiviral Res. 71 (2006) 7
17. Tseng Y.P., Kuo Y.H., Hu C.P., Jeng K.S., Janmanchi D., Lin C.H., Chou C.K., and Yeh S.F. Antiviral Res. 77 (2008) 206
18. Li Y., Fu L., Yeo H., Zhu J.L., Chou C.K., Kou Y.H., Yeh S.F., Gullen E., Austin D., and Cheng Y.C. Antiviral Chem. Chemother. 16 (2005) 193
19. Mizufune H., Nakamura M., and Mitsudera H. Tetrahedron Lett. 42 (2001) 437
20. Holmes T.L., and Stevenso R. J. Chem. Soc. C-Org. (1971) 2091
21. Stevenson R., and Weber J.V. J. Nat. Prod. 52 (1989) 367
22. Charlton J.L., Oleschuk C.J., and Chee G.L. J. Org. Chem. 61 (1996) 3452
23. Yeo H., Li Y., Fu L., Zhu J.L., Gullen E.A., Dutschman G.E., Lee Y., Chung R., Huang E.S., Austin D.J., and Cheng Y.C. J. Med. Chem. 48 (2005) 534
24. Cow C., Leung C., and Charlton J.L. Can. J. Chem.-Revue Canadienne De Chim. 78 (2000) 553
25. Yeh S.F., Hong C.Y., Huang Y.L., Liu T.Y., Choo K.B., and Chou C.K. Antiviral Res. 20 (1993) 185
26. Chou Y.C., Jeng K.S., Chen M.L., Liu H.H., Liu T.L., Chen Y.L., Liu Y.C., Hu C.P., and Chang C. J. Virol. 79 (2005) 1813
27. Ying C., Li Y., Leung C.H., Robek M.D., and Cheng Y.C. Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 8526
28. Chang C.M., Jeng K.S., Hu C.P., Lo S.J., Su T.S., Ting L.P., Chou C.K., Han S.H., Pfaff E., Salfeld J., et al. EMBO J. 6 (1987) 675
29. Huang R.L., Huang Q., Chen C.F., Chang T.T., and Chou C.J. Chin. Pharm. J. 55 (2003) 371
30. Gruffat D., Piot C., Durand D., and Bauchart D. Anal. Biochem. 242 (1996) 77
31. Mullis K., Faloona F., Scharf S., Saiki R., Horn G., and Erlich H. Cold Spring Harb. Symp. Quant. Biol. 51 (1986) 263
32. Galibert F., Mandart E., Fitoussi F., Tiollais P., and Charnay P. Nature 281 (1979) 646