Synthesis of 5,6-Dihydro-OSW-1 and its antitumor activities†
Le-Hua Deng
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorHao Wu
Institute of Biochemistry and Cell Biology, Shanghai Institute for Biological Sciences, Chinese Academy of Sciences, Shanghai 200031, China
Search for more papers by this authorBiao Yu
Institute of Biochemistry and Cell Biology, Shanghai Institute for Biological Sciences, Chinese Academy of Sciences, Shanghai 200031, China
Search for more papers by this authorMan-Rong Jiang
Institute of Biochemistry and Cell Biology, Shanghai Institute for Biological Sciences, Chinese Academy of Sciences, Shanghai 200031, China
Search for more papers by this authorJia-Rui Wu
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorLe-Hua Deng
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorHao Wu
Institute of Biochemistry and Cell Biology, Shanghai Institute for Biological Sciences, Chinese Academy of Sciences, Shanghai 200031, China
Search for more papers by this authorBiao Yu
Institute of Biochemistry and Cell Biology, Shanghai Institute for Biological Sciences, Chinese Academy of Sciences, Shanghai 200031, China
Search for more papers by this authorMan-Rong Jiang
Institute of Biochemistry and Cell Biology, Shanghai Institute for Biological Sciences, Chinese Academy of Sciences, Shanghai 200031, China
Search for more papers by this authorJia-Rui Wu
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorDedicated to Professor Chengye Yuan on the occasion of his 80th birthday.
Abstract
5,6-Dihydro-OSW-1 (1) was synthesized following our previous procedure for the total synthesis of OSW-1. This compound demonstrated slightly stronger potency than that of OSW-1 against the growth of cancer cells.
References
- 1 Kubo, S.; Mimaki, Y.; Terao, M.; Sashida, Y.; Nikaido, T.; Ohoto, T. Phytochemistry 1992, 31, 3969.
- 2 Mimaki, Y.; Kuroda, M.; Kameyarna, A.; Sashida, Y.; Hirano, T.; Oka, K.; Maekawa, R.; Wada, T.; Sugita, K.; Beutler, J. A. Bioorg. Med. Chem. Lett. 1997, 7, 633.
- 3 Kuroda, M.; Mimaki, Y.; Yokosuka, A.; Sashitla, Y.; Beutler, J. A. J. Nat. Prod. 2001, 64, 88.
- 4 Kuroda, M.; Mimaki, Y.; Yokosuka, A.; Sashida, Y. Chem. Pharm. Bull. 2001, 49, 1042.
- 5 Kuroda, M.; Mimaki, Y.; Yokosuka, A.; Hasegawa, F.; Sashida, Y. J. Nat. Prod. 2002, 65, 1417.
- 6 Ma, X.; Yu, B.; Hui, Y.; Miao, Z.; Ding, J. Bioorg. Med. Chem Lett. 2001, 11, 2153.
- 7 Deng, S.; Yu, B.; Lou, Y.; Hui, Y. J. Org. Chem 1999, 64, 202.
- 8 Mappus, E.; Renauld, M.; de Ravel, M. R.; Grenot, C.; Cuilleron, C. Y. Steroid 1992, 57, 122.
- 9 Avallone, E.; Izzo, I.; Vuolo, G.; Costabile, M.; Garrisi, D.; Pasquato, L.; Scrimin, P.; Tecilla, P.; De Riccardis, F. Tetrahedron Lett. 2003, 44, 6121.
- 10 Izzo, I.; Pironti, V.; Monica, C. D.; Sodano, G., De Riccardis, F.. Tetrahedron Lett. 2001, 42, 8977.
- 11 Paquette, L. A.; Wang, H. L.; Su, Z.; Zhao, M. Z. J. Am. Chem. Soc. 1998, 120, 5213.
- 12 Xu, Q. H.; Peng, X. W.; Tian, W. S. Tetrahedron Lett. 2003, 44, 9375.
- 13 Shen, D.; Akiyama, S.; Schoenlein, P.; Pastan, P.; Gottesman, M. Br. J. Cancer 1995, 71, 676.
- 14 Kim, Y.; Song, R.; Chung, H.; Jun, M.; Soh, Y. J. Inorg. Biochem. 2004, 98, 98.
- 15 Kwon, Y.; Whang, K.; Park, Y.; Kim, K. Bioorg. Med. Chem. 2003, 11, 1669.