Design, synthesis and structure-activity relationships studies on the d ring of the natural product triptolide

ChemMedChem

Volumn 9, Issue 2, 2014, Pages 290-295

  Xu, Hongtao ^a   Tang, Huanyu ^a   Feng, Huijin ^a   Li, Yuanchao ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Antitumor Agents; Cytotoxicity; Natural Products; Structure Activity Relationships; Triptolide

Indexed keywords

FURAN; LACTONE; TRIPTOLIDE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CHEMICAL MODIFICATION; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; FEMALE; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; HYDROGEN BOND; MALE; OVARY CARCINOMA; PRIORITY JOURNAL; PROSTATE CARCINOMA; STRUCTURE ACTIVITY RELATION;

ANTITUMOR AGENTS; CYTOTOXICITY; NATURAL PRODUCTS; STRUCTURE-ACTIVITY RELATIONSHIPS; TRIPTOLIDE;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; DITERPENES; DRUG DESIGN; EPOXY COMPOUNDS; FEMALE; HUMANS; MALE; MODELS, MOLECULAR; OVARIAN NEOPLASMS; OVARY; PHENANTHRENES; PROSTATE; PROSTATIC NEOPLASMS; STRUCTURE-ACTIVITY RELATIONSHIP; TRIPTERYGIUM;

EID: 84897025126     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201300409     Document Type: Article

References (34)

1. M. Kupchan, W. A. Court, R. G. Dailey, Jr., C. J. Gilmore, R. F. Bryan, J. Am. Chem. Soc. 1972, 94, 7194.
2. S. Huang, The Saint Peasant's Scripture of Materia Medica (18357), The Publishing House for Chinese Medicine Classics, Beijing, republished in 1982, pp. 309-310.
3. X. X. Wang, R. Matta, G. Shen, L. D. Nelin, D. H. Pei, Y. S. Liu, J. Mol. Med. 2006, 84, 405.
4. G. S. Ding, Clin. Ther. 1987, 9, 345.
5. S. M. Kupchan, R. M. Schubert, Science 1974, 185, 791.
6. K. Y. Lee, W.-T. Chang, D.-M. Qiu, P. N. Kao, G. D. Rosen, J. Biol. Chem. 1999, 274, 13451.
7. Y. L. Zheng, J. F. Lin, C. C. Lin, Y. Xu, Acta Pharm. Sin. 1994, 15, 540.
8. J. R. Zheng, K. X. Gu, L. F. Xu, J. W. Gao, Y. H. Yu, M. Y. Tang, Acta Acad. Med. Sin. 1991, 13, 391.
9. W. Z. Gu, R. Chen, S. Brandwein, J. McAlpine, N. Burres, Int. J. Immunopharmacol. 1995, 17, 351.
10. S.-X. Yang, H. L. Gao, S. S. Xie, W. R. Zhang, Z.-Z. Long, Int. J. Immunopharmacol. 1992, 14, 963.
11. D. M. Qiu, G. H. Zhao, Y. Aoki, L. F. Shi, A. Uyei, S. Nazarian, J. C. H. Ng, P. N. Kao, J. Biol. Chem. 1999, 274, 13443.
12. Q. S. Zhen, X. Ye, Z. J. Wei, Contraception 1995, 51, 121.
13. J. R. Zheng, J. L. Fang, K. X. Gu, Y. Q. Yin, L. F. Xu, J. W. Gao, H. Z. Guo, Y. H. Yu, H. Z. Sun, Acta. Acad. Med. Sin. 1987, 9, 323.
14. S. Yang, J. Chen, Z. Guo, X.-M. Xu, L. Wang, X.-F. Pei, J. Yang, C. B. Underhill, L. Zhang, Mol. Cancer Ther. 2003, 2, 65.
15. Y. Yang, Z. Liu, E. Tolosa, J. Yang, L. Li, Immunopharmacology 1998, 40, 139.
16. B. J. Chen, Leuk. Lymphoma 2001, 42, 253.
17. L. A. Shamon, J. M. Pezzuto, J. M. Graves, R. R. Mehta, S. Wangcharoentrakul, R. Sangsuwan, S. Chaichana, P. Tuchinda, P. Cleason, V. Reutrakul, Cancer Lett. 1997, 112, 113.
18. T. M. Kiviharju, P. S. Lecane, R. G. Sellers, D. M. Peehl, Clin. Cancer Res. 2002, 8, 2666.
19. B. Z. Carter, D. H. Mak, W. D. Schober, T. McQueen, D. Harris, Z. Estrov, R. L. Evans, M. Andreeff, Blood 2006, 108, 630.
20. T. Tengchaisri, R. Chawengkirttikul, N. Rachaphaew, V. Reutrakul, R. Sangsuwan, S. Sirisinha, Cancer Lett. 1998, 133, 169.
21. W. T. Chang, J. J. Kang, K. Y. Lee, K. Wei, E. Anderson, S. Gotmare, J. A. Ross, G. D. Rosen, J. Biol. Chem. 2001, 276, 2221.
22. S. Frese, F. Pirnia, D. Miescher, S. Krajewski, M. M. Borner, J. C. Reed, R. A. Schmid, Oncogene 2003, 22, 5427.
23. S. D. Westerheide, T. L. Kawahara, K. Orton, R. I. Morimoto, J. Biol. Chem. 2006, 281, 9616.
24. J. M. Fidler, K. Li, C. Chung, K. Wei, J. A. Ross, M. Gao, G. D. Rosen, Mol. Cancer Ther. 2003, 2, 855.
25. B. Zhou, X. M. Li, H. T. Tang, Z. H. Miao, H. J. Feng, Y. C. Li, Org. Biomol. Chem. 2011, 9, 3176.
26. Y. Aoyagi, Y. Hitotsuyanagi, T. Hasuda, H. Fukaya, K. Takeya, R. Aiyama, T. Matsuzaki, S. Hashimoto, Bioorg. Med. Chem. Lett. 2011, 21, 3046.
27. B. Zhou, X. M. Li, H. J. Feng, Y. C. Li, Tetrahedron 2010, 66, 5396.
28. H. Becker, T. Bremholt, E. Adler, Tetrahedron Lett. 1972, 13, 4205.
29. D. Yang, X. Y. Ye, M. Xu, J. Org. Chem. 2000, 65, 2208.
30. K. Tamao, N. Ishida, Y. Ito, M. Kumada, Org. Synth. 1990, 69, 96.
31. Z. Li, Z. L. Zhou, Z. H. Miao, L. P. Lin, H. J. Feng, L. J. Tong, J. Ding, Y. C. Li, J. Med. Chem. 2009, 52, 5115.
32. B. S. Bal, W. E. Childers, Jr., H. W. Pinnick, Tetrahedron 1981, 37, 2091.
33. M. R. Kernan, D. J. Faulkner, J. Org. Chem. 1988, 53, 2773.
34. L. V. Rubinstein, R. H. Shoemaker, K. D. Paull, R. M. Simon, S. Tosini, P. Skehan, D. A. Scudiero, A. Monks, M. R. Boyd, J. Natl. Cancer Inst. 1990, 82, 1113.