Regioselective synthesis and in vitro anticancer activity of 4-aza-podophyllotoxin derivatives catalyzed by l -proline

Journal of Combinatorial Chemistry

Volumn 12, Issue 4, 2010, Pages 430-434

  Shi, Chunling ^a   Wang, Juxian ^b   Chen, Hui ^a   Shi, Daqing ^a  

^a SOOCHOW UNIVERSITY   (China)

^b INSTITUTE OF MEDICINAL BIOTECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; HETEROCYCLIC COMPOUND; PODOPHYLLOTOXIN; PROLINE;

ARTICLE; CATALYSIS; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; DRUG SCREENING; HUMAN; STEREOISOMERISM; SYNTHESIS; TUMOR CELL LINE; X RAY CRYSTALLOGRAPHY; DRUG EFFECTS;

ANTINEOPLASTIC AGENTS; AZA COMPOUNDS; CATALYSIS; CELL LINE, TUMOR; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PODOPHYLLOTOXIN; PROLINE; STEREOISOMERISM;

EID: 77954558876     PISSN: 15204766     EISSN: 15204774     Source Type: Journal    
DOI: 10.1021/cc100003c     Document Type: Article

References (29)

1. Eycken, J. V., Bosmans, J. P., Haver, D. V., Vandewalle, M., Hulkenberg, A., Veerman, W., and Nieuwenhuizeu, R. Tetrahedron Lett. 1989, 30, 3873-3876
2. Tomioka, K., Kubota, Y., and Koga, K. Tetrahedron Lett. 1989, 30, 2953-2954
3. Bosmans, J. P., Eycken, J. V., Vandewalle, M., Hulkenberg, A., Hes, R. V., and Veerman, W. Tetrahedron Lett. 1989, 30, 3877-3880
4. Tomioka, K., Kubota, Y., and Koga, K. Tetrahedron 1993, 49, 1891-1900
5. Lienard, P., Royer, J., Quirion, J. C., and Husson, H. P. Tetrahedron Lett. 1991, 32, 2489-2492
6. Poli, G. and Giambastiani, G. J. Org. Chem. 2002, 67, 9456-9459
7. Hitosuyanagi, Y., Kobayashi, M., Fukuyo, M., Takeya, K., and Itokawa, H. Tetrahedron Lett. 1997, 38, 8295-8296
8. Hitosuyanagi, Y., Kobayashi, M., Morita, H., Itokawa, H., and Takeya, K. Tetrahedron Lett. 1999, 40, 9107-9110
9. Tratrat, C., Renault, S. G., and Husson, H. P. Org. Lett. 2002, 4, 3187-3189
10. Tu, S. J., Zhang, Y., Zhang, J. Y., Jiang, B., Jia, R. H., Zhang, J. P., and Ji, S. J. Synlett 2006, 2785-2790
11. Chandrasekhar, S., Reddy, N. S., Sultana, S. S., Narsihmulu, C., and Reddy, K. V. Tetrahedron 2006, 62, 338-345
12. Li, H., Wang, B., and Deng, L. J. Am. Chem. Soc. 2006, 128, 732-733
13. Alcaide, B., Almendros, P., Luna, A., and Torres, M. R. J. Org. Chem. 2006, 71, 4818-4822
14. List, B., Pojarliey, P., Biller, W. T., and Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827-833
15. Janey, J. M., Hsiao, Y., and Armstrong, J. D., III J. Org. Chem. 2006, 71, 390-392
16. Rasalkar, M. S., Potdar, M. K., Mohile, S. S., and Salunkhe, M. M. J. Mol. Catal. A: Chem. 2005, 235, 267-270
17. Kotrusz, P. and Toma, S. Molecules 2006, 11, 197-205
18. Kotrusz, P. and Toma, S. Arkivoc 2006, 100-109
19. Ramachary, D. B., Chowdari, N. S., and Barbas, C. F., III Angew. Chem. 2003, 115, 4365-4369
20. Bogevig, A., Juhl, K., Kumaragurubaran, N., Zhuang, W., and Jorgensen, K. A. Angew. Chem., Int. Ed. 2002, 41, 1790-1793
21. Hossein, A. O., Elham, R., and Majid, M. H. J. Chem. Res. 2006, 246-247
22. Yadav, J. S., Kumar, S. P., Kondaji, G., Rao, R. S., and Nagaiah, K. Chem. Lett. 2004, 33, 1168-1169
23. Mabry, J. and Ganem, B. Tetrahedron Lett. 2006, 47, 55-56
24. Kumar, A. and Maurya, R. A. Tetrahedron 2007, 63, 1946-1952
25. Shi, C. L., Shi, D. Q., Kim, S. H., Huang, Z. B., Ji, S. J., and Ji, M. Tetrahedron 2008, 64, 2425-2432
26. Shi, C. L., Shi, D. Q., Kim, S. H., Huang, Z. B., and Ji, M. Aust. J. Chem. 2008, 61, 547-551
27. Li, Y. L., Chen, H., Shi, C. L., Shi, D. Q., and Ji, S. J. J. Comb. Chem. 2010, 12, 231-237
28. 2 cells were incubated in MEM culture medium containing 10% blood serum. The cells were plated in flat-bottomed 96-well plates (5000 cells/well) and cultured for 24 h in controlled atmosphere. Then certain concentrations of products (100, 10, or 20 mg/mL in DMSO) were diluted 1000 times and added to the culture using DMSO as control solution. After 24 h, the absorbencies were read at 592 and 570 nm with SRB assay.
29. Indumathi, S., Perumal, S., and Menendez, J. C. J. Org. Chem. 2010, 75, 472-475