Synthesis and biological evaluation of helioxanthin analogues

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 7, 2013, Pages 2163-2176

  Janmanchi, Damodar ^a,b   Lin, Chih Hsiu ^a   Hsieh, Jui Yu ^b   Tseng, Ya Ping ^b   Chen, Tai An ^b   Jhuang, Hong Jhih ^b   Yeh, Sheau Farn ^b  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

^b NATIONAL YANG MING UNIVERSITY   (Taiwan)

Author keywords

Anti HBV agents; Helioxanthin derivatives; Hepatitis B virus; Structure activity relation

Indexed keywords

10 (2,2 DIFLUOROBENZO[D][1,3]DIOXOL 5 YL)FURO[30,40:6,7]NAPHTHO[1,2 D][1,3]DIOXOLE 7,9 DIONE; 10 (3 BENZYLOXY 4 METHOXYPHENYL)FURO[30,40:6,7]NAPHTHO[1,2 D][1,3]DIOXOL 7,9 DIONE; 10 (3 HYDROXY 4 METHOXYPHENYL)FURO[30,40:6,7]NAPHTHO[1,2 D][1,3]DIOXOL 9(7H) ONE; 10 (3 HYDROXY 4 METHOXYPHENYL)FURO[30,40:6,7]NAPHTHO[1,2 D][1,3]DIOXOL 9(7H)ONE; 10 (3,4 BIS BENZYLOXYPHENYL)FURO[30,40:6,7]NAPHTH[1,2 D][1,3]DIOXOLE 7,9 DIONE; 10 (3,4 DIHYDROXYPHENYL)FURO[30,40:6,7]NAPHTHO[1,2 D][1,3]DIOXOL 9(7H)ONE; 10 (3,4 DIMETHOXYPHENYL)FURO[30,40:6,7]NAPHTHO[1,2 D][1,3]DIOXOLE 7,9 DIONE; 10 (4 BENZYLOXY 3 METHOXY PHENYL)FURO[30,40:6,7]NAPHTHO[1,2 D][1,3]DIOXOL 7,9 DIONE; 10 (4 HYDROXY 3 METHOXYPHENYL)FURO[30,40:6,7]NAPHTHO[1,2 D][1,3]DIOXOL 9(7H)ONE; 2 METHOXY 4 (7 OXO 7,9 DIHYDROFURO[30,40:6,7]NAPHTHO[1,2 D][1,3]DIOXOL 10 YL)PHENYLACETATE; 2 METHOXY 5 (7 OXO 7,9 DIHYDROFURO[30,40:6,7]NAPHTHO[1,2 D][1,3]DIOXOL 10 YL)PHENYLACETATE; 4 [7,8 BIS(HYDROXYMETHYL)NAPHTHO[1,2 D][1,3]DIOXOL 9 YL]BENZENE 1,2 DIOL; 9 (BENZO[D][1,3]DIOXOL 5 YL)NAPHTHO[1,2 D][1,3]DIOXOLE 7,8 DICARBONITRILE; [9 (3,4 DIMETHOXYPHENYL) 8 (HYDROXYMETHYL)NAPHTHO[1,2 D][1,3]DIOXOL 7 YL]METHYLACETATE; [9 (3,4 DIMETHOXYPHENYL) 8 (HYDROXYMETHYL)NAPHTHO[1,2 D][1,3]DIOXOL 7 YL]METHYLHEXANOATE; [9 (3,4 DIMETHOXYPHENYL)NAPHTHO[1,2 D][1,3]DIOXOLE 7,8 DIYL]BIS(METHYLENE)DIACETATE; [9 (4 HYDROXY 3 METHOXYPHENYL)NAPHTHO[1,2 D][1,3]DIOXOLE 7,8 DIYL]DIMETHANOL; [9 (BENZO[D][1,3]DIOXOL 5 YL) 8 (HYDROXYMETHYL)NAPHTHO[1,2 D][1,3]DIOXOL 7 YL]METHYLHEXANOATE; [9 (BENZO[D][1,3]DIOXOL 5 YL)NAPHTHO[1,2 D][1,3]DIOXOLE 7,8 DIYL]BIS(METHYLENE)DIHEXANOATE; ADEFOVIR; ANTIVIRUS AGENT; BAY 41 4109; HELIOXANTHIN; HELIOXANTHIN DERIVATIVE; HEPATITIS B SURFACE ANTIGEN; LAMIVUDINE; LIGNAN DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VIRUS DNA; VIRUS RNA;

ANTIVIRAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; GENE EXPRESSION; HEPATITIS B VIRUS; HUMAN; HUMAN CELL; NONHUMAN; PROMOTER REGION; VIRUS INHIBITION;

ANTIVIRAL AGENTS; DNA, VIRAL; GENE EXPRESSION REGULATION, VIRAL; HEP G2 CELLS; HEPATITIS B; HEPATITIS B VIRUS; HUMANS; LIGNANS; RNA, VIRAL; STRUCTURE-ACTIVITY RELATIONSHIP;

HEPATITIS B VIRUS;

EID: 84875215188     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.11.037     Document Type: Article

References (39)

1. World Health Organization. Hepatitis B. World Health Organization Fact Sheet 204 (Revised August 2008). (http://www.who.int/mediacentre/factsheets/ fs204/en/index.html).
2. W.S. Robinson Annu. Rev. Microbiol. 31 1977 357
3. Lok, and McMahon Hepatology 45 2007 2
4. K.R. Pang, J.J. Wu, D.B. Huang, S.K. Tyring, and S. Baron Methods Mol. Med. 116 2005 1
5. F. Zoulim J. Clin. Virol. 21 2001 243
6. J.L. Dienstag, and N. Perril Engl. J. Med. 333 1995 1657
7. Walsh, K. M.; Woodlo, R. P.; Schiff, E. R.; Bartholomew, M.; Vicary, C.; Rubin, Mall, T.; Lamy, P.; Wight, D. G.; Bloor, S.; Alexander, G. J. Gut 2001, 49, 436.
8. J. Franco, and K.J. Saeian Vasc. Interv. Radiol. 13 2002 S191
9. D.R. Langley, A.W. Walsh, C.J. Baldick, B.J. Eggers, R.E. Rose, S.M. Levine, A.J. Kapur, R.J. Colonno, and D.J. Tenney J. Virol. 81 2007 3992
10. A. Ruiz-Sancho, J. Sheldon, and V. Soriano Expert. Opin. Biol. Ther. 7 2007 751
11. H.S. Lee, Y.H. Chung, K.S. Lee, K.S. Byun, S.W. Paik, J.Y. Han, K. Yoo, H.W. Yoo, J.H. Lee, and B.C. Yoo Hepatology 43 2006 982
12. C.T. Yeh, R.N. Chien, C.M. Chu, and Y.F. Liaw Hepatology 31 2000 1318
13. S. Locarnini, and W.S. Mason J. Hepatol. 44 2006 422
14. K. Deres, C.H. Schroder, A. Paessens, S. Goldmann, H.J. Hacker, O. Weber, T. Kramer, U. Niewohner, U. Pleiss, J. Stoltefuss, E. Graef, D. Koletzki, R.N. Masantschek, A. Reimann, R. Jaeger, R. Gross, B. Beckermann, K.H. Schlemmer, D. Haebich, and R.W. Helga Science 299 2003 893
15. L. Sanghyun, S.B. Hyun, P.K. Yong, K. Bak-Kwang, H.C. Seon, O. Kazuo, and S. Hyun Phytother. Res. 19 2005 103
16. Y.H. Kuo, M.D. Wu, C.C. Hung, R.L. Huang, L.M. Yang Kuo, Y.C. Shen, and C.W. Ong Bioorg. Med. Chem. 13 2005 1555
17. Y.C. Cheng, C.X. Ying, C.H. Leung, and Y. Li J. Clin. Virol. 34 2005 S147
18. H. Yeo, Y. Li, L. Fu, J.L. Zhu, E.A. Gullen, G.E. Dutschman, Y. Lee, R. Chung, E.S. Huang, D.J. Austin, and Y.C. Cheng J. Med. Chem. 2 2005 534
19. K. He, L. Zeng, G. Shi, G.X. Zhao, J.F. Kozlowski, and J.L. McLaughlin J. Nat. Prod. 60 1997 38
20. R.S. Burden, L. Crombie, and D.A. Whiting Tetrahedron Lett. 1968 1035
21. Y.P. Tseng, Y.H. Kuo, C.P. Hu, K.S. Jeng, D. Janmanchi, C.H. Lin, C.K. Chou, and S.F. Yeh Antiviral Res. 77 2008 206
22. Y. Li, L. Fu, H. Yeo, J.L. Zhu, C.K. Chou, Y.H. Kou, S.F. Yeh, E. Gullen, D. Austin, and Y.C. Cheng Antiviral Chem. Chemother. 16 2005 193
23. Janmanchi, D.; Tseng, Y. P.; Wang, K. C.; Huang, R. L.; Lin, C. H.; Yeh, S. F. Bioorg. Med. Chem. 2010, 18, 1213-1226. Ying, C. X.
24. Y. Li, C.H. Leung, M.D. Robek, and Y.C. Cheng Proc. Natl. Acad. Sci. U.S.A. 104 2007 8526
25. T.L. Holmes, and R. Stevenso J. Chem. Soc. C-Org. 1971 2091
26. R. Stevenson, and J.V. Weber J. Nat. Prod. 52 1989 367
27. H. Mizufune, M. Nakamura, and H. Mitsudera Tetrahedron Lett. 42 2001 437
28. J.L. Charlton, C.J. Oleschuk, and G.L. Chee J. Org. Chem. 61 1996 3452
29. J. Wan, B. Wu, and Y. Pan Tetrahedron 63 2007 9338
30. Grigg, R.; Gunaratne, H. Q. N.; Sridharan, V. J. Chem. Soc., Chem. Commun. 1985, 1183.
31. Yeh, S. F.; Hong, C.Y.; Huang, Y. L.; Liu, T. Y.; Choo, K. B.; Chou, C. K. Antiviral Res. 1993, 20, 185-193.
32. Y.C. Chou, K.S. Jeng, M.L. Chen, H.H. Liu, T.L. Liu, Y.L. Chen, Y.C. Liu, C.P. Hu, and C. Chang J. Virol. 2005 1813 79
33. S. Gilbert, L. Galarneau, A. Lamontagne, S. Roy, and L. B́elanger J. Virol. 74 2000 5032
34. J. Li, and J.H. Ou J. Virol. 75 2001 8400
35. X. Yu, and J.E. Mertz J. Virol. 77 2003 2489
36. C.M. Chang, K.S. Jeng, C.P. Hu, S.J. Lo, T.S. Su, L.P. Ting, C.K. Chou, S.H. Han, E. Pfaff, and J. Salfeld EMBO J. 6 1987 675
37. F. Denizot, and R. Lang J. Immunol. Methods 89 2 1986 271
38. D. Gruffat, C. Piot, D. Durand, and D. Bauchart Anal. Biochem. 242 1996 77
39. F. Galibert, E. Mandart, F. Fitoussi, P. Tiollais, and P. Charnay Nature 281 1979 646