Synthesis and biological evaluation of dihydrobenzofuran lignans and related compounds as potential antitumor agents that inhibit tubulin polymerization

Journal of Medicinal Chemistry

Volumn 42, Issue 26, 1999, Pages 5475-5481

  Pieters, Luc ^a   Van Dyck, Stefaan ^a   Gao, Mei ^a   Bai, Ruoli ^b   Hamel, Ernest ^c   Vlietinck, Arnold ^a   Lemière, Guy ^a  

^a UNIVERSITY OF ANTWERP   (Belgium)

^b SAIC FREDERICK INC   (United States)

^c NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 [2 (3,4 DIHYDROXYPHENYL) 7 HYDROXY 3 METHOXYCARBONYL 2,3 DIHYDRO 1 BENZOFURAN 5 YL]PROP 2 ENOIC ACID METHYL ESTER; ANTINEOPLASTIC AGENT; BENZOFURAN DERIVATIVE; DIHYDROBENZOFURAN DERIVATIVE; LIGNAN; TUBULIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA; PROTEIN POLYMERIZATION;

ANTINEOPLASTIC AGENTS; BENZOFURANS; BIOPOLYMERS; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; LIGNANS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; STRUCTURE-ACTIVITY RELATIONSHIP; TUBULIN; TUBULIN MODULATORS; TUMOR CELLS, CULTURED;

EID: 0033619997     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990251m     Document Type: Article

References (20)

1. Pieters, L.; De Bruyne, T.; Claeys, M.; Vlietinck, A.; Calomme, M.; Vanden Berghe, D. Isolation of a Dihydrobenzofuran Lignan from South American Dragon's Blood (Croton spp.) as an Inhibitor of Cell Proliferation. J. Nat. Prod. 1993, 56, 899-906.
2. Lemière, G.; Gao, M.; De Groot, A.; Dommisse, R.; Lepoivre, J.; Pieters, L.; Buss, V. 3′,4-Di-O-methylcedrusin: Synthesis, Resolution and Absolute Configuration. J. Chem. Soc., Perkin Trans. 1 1995, 1775-1779.
3. Ward, R. S. The Synthesis of Lignans and Neolignans. Chem. Soc. Rev. 1982, 11, 75-125.
4. MacRae, W. D.; Towers, G. H. N. Biological Activities of Lignans. Phytochemistry 1984, 23, 1207-1220.
5. Ohioccara, F.; Poli, S.; Rindone, B.; Pilati, T.; Brunow, G.; Pietikäínen, P.; Setälä, H. Regio-Selective and Diastereo-Selective Synthesis of Dimeric Lignans Using Oxidative Coupling. Acta Chem. Scand. 1993, 47, 610-616.
6. Tamada, M.; Endo, K.; Hikino, H.; Kabuto, C. Structure of Ephedradine A, a Hypotensive Principle of Ephedra Roots. Tetrahedron Lett. 1979, 873-876.
7. Yuen, M. S. M.; Xue, F.; Mak, T. C. W.; Wong, H. N. C. On the Absolute Structure of Optically Active Neolignans Containing a Dihydrobenzo[b]furan skeleton. Tetrahedron 1998, 54, 12429-12444.
8. Paull, K. D.; Shoemaker, R. H.; Hodes, L.; Monks, A. P.; Scudiero, D. A.; Rubinstein, L. V.; Plowman, J.; Boyd, M. R. Display and Analysis of Patterns of Differential Activity of Drugs Against Human Tumor Cell Lines: Development of Mean Graph and COMPARE Algorithm. J. Natl. Cancer Inst. 1989, 81, 1088-1092.
9. Pettit, G. R.; Singh, S. B.; Niven, M. L.; Hamel, E.; Schmidt, J. M. Isolation, Structure and Synthesis of Combretastatins A-1 and B-1, Potent New Inhibitors of Microtubule Assembly, Derived from Combretum Caffrum. J. Nat. Prod. 1987, 50, 119-131.
10. Leping, L.; Wang, H.-K.; Kuo, S.-C.; Wu, T.-S.; Lednicer, D.; Lin, C. M.; Hamel, E.; Lee, K.-H. Antitumor Agents. 150.2′,3′,4′,5′,5,6,7-Substituted 2-Phenyl-4-Quinolones and Related Compounds: Their Synthesis, Cytotoxicity, and Inhibition of Tubulin Polymerization. J. Med. Chem. 1994, 37, 1126-1135.
11. Hamel, E. Antimitotic Natural Products and Their Interactions with Tubulin. Med. Res. Rev. 1996, 16, 207-231.
12. Woods, J. A.; Hadfield, J. A.; Pettit, G. R.; Fox, B. W.; McGown, A. T. The Interaction With Tubulin of a Series of Stilbenes Based on Combretastatin A-4. Br. J. Cancer 1995, 71, 705-711.
13. Chen, K.; Kuo, S.-C.; Hsieh, M.-C.; Mauger, A.; Lin, C. M.; Hamel, E.; Lee, K.-H. Antitumor Agents. 174. 2′,3′,4′,5,6,7-Substituted 2-Phenyl-1,8-Naphthyridin-4-ones: Their Synthesis, Cytotoxicity, and Inhibition of Tubulin Polymerization. J. Med. Chem. 1997, 40, 2266-2275.
14. Edwards, M. L.; Stemerick, D. M.; Sunkara, P. S. Chalcones: A New Class of Antimitotic Agents. J. Med. Chem. 1990, 33, 1948-1954.
15. Beutler, J. A.; Hamel, E.; Vlietinck, A. J.; Haemers, A.; Rajan, P.; Roitman, J. N.; Cardellina, J. H. II; Boyd, M. R. Structure-Activity Requirements for Flavone Cytotoxicity and Binding to Tubulin. J. Med. Chem. 1998, 47, 2333-2338.
16. Cheng, C. C. A Common Structural Pattern Among Many Biologically Active Compounds of Natural and Synthetic Origin. Med. Hypotheszz 1986, 20, 157-172.
17. Boyd, M. R.; Paull, K. D. Some Practical Considerations and Applications of the National Cancer Institute In Vitro Anticancer Drug Discovery Screen. Drug Dev. Res. 1995, 34, 91-109.
18. Verdier-Pinard, P.; Lai, J.-L.; Yoo, H.-D.; Yu, J.; Marquez, D. G.; Nagle, M.; Nambu, J. D.; White, J. R.; Falck, W. H.: Gerwick, B. W.; Day, B. W.; Hamel, E. Structure-Activity Analysis of the Interaction of Curacin A, the Potent Colchicine Site Antimitotic Agent, with Tubulin and Effects of Analogues on the Growth of MCF-7 Breast Cancer Cells. Mol. Pharmacol. 1998, 53, 62-76.
19. Paull, K. D.; Lin, C. M.; Malspeis, L.; Hamel, E. Identification of Novel Antimitotic Agents Acting at the Tubulin Level by Computer-Assisted Evaluation of Differential Cytotoxicity Data. Cancer Res. 1992, 52, 3892-3900.
20. Hollingshead, M. G.; Alley, M. C.; Camalier, R. F.; Abbott, B. J.; Mayo, J. G.; Malspeis, L.; Grever, M. R. In Vivo Cultivation of Tumor Cells in Hollow Fibers. Life Sci. 1995, 57, 131-141.