Synthesis and antitumor activities of phenanthrene-based alkaloids

Molecules

Volumn 14, Issue 12, 2009, Pages 5042-5053

  Li, Songtao ^a   Han, Li ^a   Sun, Liang ^a   Zheng, Dan ^a   Liu, Jiang ^a   Fu, Yingbo ^a   Huang, Xueshi ^a   Wang, Zhanyou ^a  

^a CHINA MEDICAL UNIVERSITY   (China)

Author keywords

Cytotoxicity; Pbts; Synthesis

Indexed keywords

ALKALOID; ANTINEOPLASTIC AGENT; PHENANTHRENE; PHENANTHRENE DERIVATIVE;

ARTICLE; CHEMISTRY; DRUG SCREENING; ELECTROSPRAY MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ALKALOIDS; ANTINEOPLASTIC AGENTS; DRUG SCREENING ASSAYS, ANTITUMOR; MAGNETIC RESONANCE SPECTROSCOPY; PHENANTHRENES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 73849117901     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14125042     Document Type: Article

References (25)

1. Li, Z.; Jin, Z.; Huang, R. Isolation, total synthesis and biological activity of phenanthro-indolizidine and phenanthroquinolizidine alkaloids. Synthesis 2001, 16, 2365-2378.
2. Gao, W.; Lam, W.; Zhong, S.; Kaczmarek, C.; Baker, D.C.; Cheng, Y.C. Novel mode of action of tylophorine analogs as antitumor compounds. Cancer Res. 2004, 64, 678-688.
3. Gao, W.; Bussom, S.; Grill, S.P.; Gullen, E.A.; Hu, Y.; Huang, X.; Zhong, S.; Kaczmarek, C.; Gutierrez, J.; Francis, S.; Baker, D.C.; Yu, S.; Cheng, Y. Structure-activity studies of phenanthroindolizidine alkaloids as potential antitumor agents. Bioorg. Med. Chem. Lett. 2007, 17, 4338-4342.
4. Fu, Y.; Lee, S.; Min, H.; Lee, T.; Lee, J.; Cheng, M.; Kim, S. Synthesis and structure-activity studies of antofine analogues as potential anticancer agents. Bioorg. Med. Chem. Lett. 2007, 17, 97-100.
5. 2 catalyzed direct aromatic carbonylation. Eur. J. Org. Chem. 2009, 1173-1180.
6. Wei, L.; Brossi, A.; Kendall, R.; Bastow, K.F.; Morris-Natschke, S.L.; Shi, Q.; Lee, K. Antitumor agents 251: Synthesis, cytotoxic evaluation, and structure-activity relationship studies of phenanthrene-based tylophorine derivatives (PBTs) as a new class of antitumor agents. Bioorg. Med. Chem. 2006, 14, 6560-6569.
7. Wei, L.; Shi, Q.; Bastow K.F.; Brossi, A.; Susan, L.; Natschke, M.; Goto, K.; Wu, T.; Pan, S.; Teng, C.; Lee, K. Antitumor agents 253: Design, synthesis, and antitumor evaluation of novel 9-substituted phenanthrene-based tylophorine derivatives as potential anticancer agents. J. Med. Chem. 2007, 50, 3674-3680.
8. Lin, J.; Yang, S.; Hong, T.; Yu, S.; Shi, Q.; Wei, L.; Chen, H.; Yang, P.; Lee, K. Phenanthrene-based yylophorine-1 (PBT-1) inhibits lung cancer cell growth through the Akt and NF-κB pathways. J. Med. Chem. 2009, 52, 1903-1911.
9. Yang, X.; Shi, Q.; Liu, Y.; Zhao, G.; Bastow, K.F.; Lin, J.; Yang, S.; Yang, P.; Lee, K. Antitumor Agents 268: Design, synthesis, and mechanistic studies of new 9-substituted phenanthrene-based tylophorine analogues as potent cytotoxic agents. J. Med. Chem. 2009, 52, 5262-5268.
10. Cragg, J.E.; Herbert, R.B.; Jackson, F.B.; Moody, C.J.; Nicolson, I.T. Phenanthroindolizidine and related alkaloids: Synthesis of tylophorine, septicine, and deoxytylophorinine. J. Chem. Soc. Perkin Trans. 1 1982, 2477-2485.
11. Wang, K.L.; Lu, M.Y.; Wang, Q.M.; Huang, R.Q. Iron(III) chloride-based mild synthesis of phenanthrene and its application to total synthesis of phenanthroindolizidine alkaloids. Tetrahedron 2008, 64, 7504-7510.
12. Russel, J.H.; Hunziker, H. Synthesis of septicine. Tetrahedron Lett. 1969, 46, 4035-4036.
13. Halton, B.; Maidment, A.I.; Officer, D.L.; Warnes, J.M. The oxidative conversion of (E)-α-(Arylmethylene)benzeneacetates into substituted phenanthrenes: The propitious use of boron trifluoride with vanadium trifluoride oxide. Aust. J. Chem. 1984, 37, 2119-2128.
14. Wang, K.L.; Lu, M.Y.; Yu, A.; Zhu, X.Q.; Wang, Q.M. Iron(III) chloride catalyzed oxidative coupling of aromatic nuclei. J. Org. Chem. 2009, 74, 935-938.
15. Montalbetti, C.A.G.N.; Falqu, V. Amide bond formation and peptide coupling. Tetrahedron 2005, 61, 10827-10852.
16. Herbert, R.B.; Moody, C.J. A novel synthesis of (±)-tylophorine. J. Chem. Soc. D 1970, 121.
17. Terakado, D.; Oriyama, T. Catalitic asymmetric acylation of alcohols using a chiral 1,2-diamine derived from (s)-proline: (1S,2S)- trans-1-benzoyloxy-2-bromo-cyclohexane. Org. Syn. 2006, 83, 70-79.
18. Govindachari, T.R.; Lakshmikantham, M.V.; Rajadurai, S. Chemical examination of Tylophora asthmatica-IV: Synthesis of tylophorine. Tetrahedron 1961, 14, 284-287.
19. Chauncy, B; Gellert, E. Synthesis of phenanthroindolizidines. II. The synthesis of (±)-tylocrebrine, (±)-tylophorine, (±)-antofine, and (±)-2,3-dimethoxyphenanthroindolizidine. Aust. J. Chem. 1970, 23, 2503-2516.
20. Liu, Y.; Lotero, E.; Goodwin, J.G. Effect of water on sulfuric acid catalyzed esterification. J. Mol. Catal. A. Chem. 2006, 245, 132-140.
21. Wadsworth, D.H. Azetidine. Org. Syn. 1973, 53, 13-16.
22. 4/TFA. Tetrahedron Lett. 1996, 37, 7213-7216.
23. 2 system. Tetrahedron 1992, 48, 4623-4628.
24. Carmichael, J.; DeGraff, W.G.; Gazdar, A.F.; Minna, J.D.; Mitchell, J.B. Evaluation of a tetrazoliumbased semiautomated colorimetric assay: assessment of chemosensitivity testing. Cancer Res. 1987, 47, 936-942.
25. Chuang, T.; Lee, S.; Yang, C.; Wu, P. Expedient synthesis and structure-activity relationships of phenanthroindolizidine and phenanthroquinolizidine alkaloids. Org. Biomol. Chem. 2006, 4, 860-867.