Efficient synthesis and biological evaluation of epiceanothic acid and related compounds

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 1, 2011, Pages 338-341

  Zhang, Pu ^a   Xu, Li ^a   Qian, Keduo ^b   Liu, Jun ^a   Zhang, Luyong ^a   Lee, Kuo Hsiung ^b,c   Sun, Hongbin ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b University of North Carolina   (United States)

^c CHINA MEDICAL UNIVERSITY   (Taiwan)

Author keywords

Anti HIV agents; Cytotoxic agents; Epiceanothic acid; Glycogen phosphorylase inhibitors; Pentacyclic triterpene

Indexed keywords

BETULIN; CEANOTHIC ACID; EPICEANOTHIC ACID; ISOCEANOTHIC ACID; TRITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CELL STRAIN MCF 7; CYTOTOXICITY; DRUG ACTIVITY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; VIRUS INHIBITION; VIRUS REPLICATION;

ANTI-HIV AGENTS; CELL LINE, TUMOR; GLYCOGEN PHOSPHORYLASE; HIV-1; HUMANS; PENTACYCLIC TRITERPENES; TRITERPENES;

HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 78650518132     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.11.004     Document Type: Article

References (35)

1. Z. Ovesna, A. Vachalkova, K. Horvathova, and D. Tothova Neoplasma 51 2004 327
2. H. Sun, W.S. Fang, W.Z. Wang, and C. Hu Bot. Stud. 47 2006 339
3. N. Sultana, and A. Ata J. Enzyme Inhib. Med. Chem. 23 2008 739
4. M.N. Laszczyk Planta Med. 75 2009 1549
5. A. Petronelli, G. Pannitteri, and U. Testa Anticancer Drugs 20 2009 880
6. Qian, K.; Nitz, T. J.; Yu, D.; Allaway, G. P.; Morris-Natschke, S. L.; Lee, K. H. Natural Product Chemistry for Drug Discovery, RSC Series. 2009, 13, 374.
7. D. Yu, C.T. Wild, D.E. Martin, S.L. Morris-Natschke, C.H. Chen, G.P. Allaway, and K.H. Lee Expert Opin. Investig. Drugs 14 2005 681
8. X.A. Wen, P. Zhang, J. Liu, L.Y. Zhang, X.M. Wu, P.Z. Ni, and H.B. Sun Bioorg. Med. Chem. Lett. 16 2006 722
9. X.A. Wen, H.B. Sun, J. Liu, K.G. Cheng, P. Zhang, L.Y. Zhang, J. Hao, P.Z. Ni, S.E. Zographos, D.D. Leonidas, K.M. Alexacou, T. Gimisis, J.M. Hayes, and N.G. Oikonomakos J. Med. Chem. 51 2008 3540
10. P. Zhang, J. Hao, J. Liu, Q. Lu, H. Sheng, L. Zhang, and H. Sun J. Nat. Prod. 72 2009 1414
11. L.-M. Li, X. Liao, S.-L. Peng, and L.-S. Ding J. Integr. Plant Biol. 47 2005 494
12. Li, W.; Zhao, W. 101062936, 2007, 15.
13. W.-H. Li, X.-M. Zhang, R.-R. Tian, Y.-T. Zheng, W.-M. Zhao, and M.-H. Qiu J. Asian Nat. Prod. Res. 9 2007 551
14. J.P. Boyer, R.A. Eade, H. Locksley, and J.J.H. Simes Aust. J. Chem. 11 1958 236
15. A.J. Birch, E. Ritchie, and R.N. Speake J. Chem. Soc. 1960 3593
16. M. Ikram, and H. Tomlinson Planta Med. 29 1976 289
17. J.N. Roitman, and L. Jurd Phytochemistry 17 1978 491
18. S.C. Sharma, and R. Kumar Pharmazie 38 1983 65
19. V.M. Merkuza, O.A. Mascaretti, R. Crohare, and E.A. Ruveda Phytochemistry 10 1971 908
20. S.-S. Lee, W.-C. Chen, C.-F. Huang, and Y. Su J. Nat. Prod. 61 1998 1343
21. S.-J. Jou, C.-H. Chen, J.-H. Guh, C.-N. Lee, and S.-S. Lee J. Chin. Chem. Soc. (Taipei, Taiwan) 51 2004 827
22. S. Suksamrarn, P. Panseeta, S. Kunchanawatta, T. Distaporn, S. Ruktasing, and A. Suksamrarn Chem. Pharm. Bull. 54 2006 535
23. K. Nakagawa-Goto, K. Yamada, M. Taniguchi, H. Tokuda, and K.-H. Lee Bioorg. Med. Chem. Lett. 19 2009 3378
24. 5+Na calcd 781.48025, found 781.48348.
25. J. Hao, P. Zhang, X. Wen, and H. Sun J. Org. Chem. 73 2008 7405
26. M. Urban, J. Sarek, J. Klinot, G. Korinkova, and M. Hajduch J. Nat. Prod. 67 2004 1100
27. T. Konoike, K. Takahashi, Y. Kitaura, and Y. Kanda Tetrahedron 55 1999 14901
28. 4-3 variants at a multiplicity of infection (MOI) of 0.01 were used to infect MT-4 cells. Culture supernatants were collected on day four post-infection for the p24 antigen capture using an ELISA kit from ZeptoMetrix Corporation (Buffalo, NY).
29. L. Huang, P. Ho, K.H. Lee, and C.H. Chen Bioorg. Med. Chem. Lett. 14 2006 2279
30. D.L. Yu, Y. Sakurai, C.H. Chen, F.R. Chang, L. Huang, Y. Kashiwada, and K.H. Lee J. Med. Chem. 49 2006 5462
31. K. Qian, D. Yu, C.H. Chen, L. Huang, S.L. Morris-Natschke, T.J. Nitz, K. Salzwedel, M. Reddick, G.P. Allaway, and K.H. Lee J. Med. Chem. 52 2009 3248
32. 50 values were estimated by fitting the inhibition data to a dose-dependent curve using a logistic derivative equation.
33. W.H. Martin, D.J. Hoover, S.J. Armento, I.A. Stock, R.K. McPherson, D.E. Danley, R.W. Stevenson, E.J. Barrett, and J.L. Treadway Proc. Natl. Acad. Sci. U.S.A. 95 1998 1776
34. 50 values were estimated by fitting the inhibition data to a dose-dependent curve using a logistic derivative equation.
35. INVITTOX. Protocol 17, 1980.