Discovery of Potent Cell Migration Inhibitors through Total Synthesis: Lessons from Structure-Activity Studies of (+)-Migrastatin

Journal of the American Chemical Society

Volumn 126, Issue 4, 2004, Pages 1038-1040

  Njardarson, Jón T ^a   Gaul, Christoph ^a   Shan, Dandan ^c   Huang, Xin Yun ^c   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

^c WEILL CORNELL MEDICAL COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM; ERYTHRONOLIDE DERIVATIVE; MIGRASTATIN; NATURAL PRODUCT; PACLITAXEL; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CELL MIGRATION; CONTROLLED STUDY; DRUG DEVELOPMENT; DRUG RESEARCH; DRUG STRUCTURE; DRUG SYNTHESIS; MIGRATION INHIBITION; STRUCTURE ACTIVITY RELATION; WOUND HEALING;

ANGIOGENESIS INHIBITORS; ANIMALS; CELL LINE, TUMOR; CELL MOVEMENT; DRUG DESIGN; ENDOTHELIUM, VASCULAR; HUMANS; LACTONES; MACROLIDES; MICE; PIPERIDONES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0942265463     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039714a     Document Type: Article

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24. For experimental details, consult the Supporting Information.
25. 50 for compounds 7 and 8 with HUVECs were 150 and 125 nM, respectively.
26. 50 for compounds 13 and 14 with HUVECs were 18 and 12 μM, respectively.
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31. A sample of synthetic epoxyquinol A was kindly provided by Professor John A. Porco, Jr. For the isolation of epoxyquinols A and B, see: Kakeya, H.; Onose, R.; Koshino, H.; Yoshida, A.; Kobayashi, K.; Kageyama, S. I.; Osada, H. J. Am. Chem. Soc. 2002, 124, 3496; Kakeya, H.; Onose, R.; Yoshida, A.; Koshino, H.; Osada, H. J. Antibiot. 2002, 55, 829. For the total synthesis of epoxyquinols A and B, see: Shoji, M.; Yamaguchi, J.; Kakeya, H.; Osada, H.; Hayashi, Y. Angew. Chem. Int. Ed, 2002, 41, 3192; Chaomin, L.; Bardhan, S.; Pace, E. A.; Liang, M. C.; Gilmore, T. D.; Porco, J. A., Jr. Org. Lett. 2002, 4, 3267; Mehta, G.; Islam, K. Tetrahedron Lett. 2003, 44, 3569.
32. A sample of synthetic epoxyquinol A was kindly provided by Professor John A. Porco, Jr. For the isolation of epoxyquinols A and B, see: Kakeya, H.; Onose, R.; Koshino, H.; Yoshida, A.; Kobayashi, K.; Kageyama, S. I.; Osada, H. J. Am. Chem. Soc. 2002, 124, 3496; Kakeya, H.; Onose, R.; Yoshida, A.; Koshino, H.; Osada, H. J. Antibiot. 2002, 55, 829. For the total synthesis of epoxyquinols A and B, see: Shoji, M.; Yamaguchi, J.; Kakeya, H.; Osada, H.; Hayashi, Y. Angew. Chem. Int. Ed, 2002, 41, 3192; Chaomin, L.; Bardhan, S.; Pace, E. A.; Liang, M. C.; Gilmore, T. D.; Porco, J. A., Jr. Org. Lett. 2002, 4, 3267; Mehta, G.; Islam, K. Tetrahedron Lett. 2003, 44, 3569.
33. A sample of synthetic epoxyquinol A was kindly provided by Professor John A. Porco, Jr. For the isolation of epoxyquinols A and B, see: Kakeya, H.; Onose, R.; Koshino, H.; Yoshida, A.; Kobayashi, K.; Kageyama, S. I.; Osada, H. J. Am. Chem. Soc. 2002, 124, 3496; Kakeya, H.; Onose, R.; Yoshida, A.; Koshino, H.; Osada, H. J. Antibiot. 2002, 55, 829. For the total synthesis of epoxyquinols A and B, see: Shoji, M.; Yamaguchi, J.; Kakeya, H.; Osada, H.; Hayashi, Y. Angew. Chem. Int. Ed, 2002, 41, 3192; Chaomin, L.; Bardhan, S.; Pace, E. A.; Liang, M. C.; Gilmore, T. D.; Porco, J. A., Jr. Org. Lett. 2002, 4, 3267; Mehta, G.; Islam, K. Tetrahedron Lett. 2003, 44, 3569.
34. A sample of synthetic epoxyquinol A was kindly provided by Professor John A. Porco, Jr. For the isolation of epoxyquinols A and B, see: Kakeya, H.; Onose, R.; Koshino, H.; Yoshida, A.; Kobayashi, K.; Kageyama, S. I.; Osada, H. J. Am. Chem. Soc. 2002, 124, 3496; Kakeya, H.; Onose, R.; Yoshida, A.; Koshino, H.; Osada, H. J. Antibiot. 2002, 55, 829. For the total synthesis of epoxyquinols A and B, see: Shoji, M.; Yamaguchi, J.; Kakeya, H.; Osada, H.; Hayashi, Y. Angew. Chem. Int. Ed, 2002, 41, 3192; Chaomin, L.; Bardhan, S.; Pace, E. A.; Liang, M. C.; Gilmore, T. D.; Porco, J. A., Jr. Org. Lett. 2002, 4, 3267; Mehta, G.; Islam, K. Tetrahedron Lett. 2003, 44, 3569.
35. A screening approach revealed the natural product evodiamine as a potent anti-invasive and anti-metastatic agent: Ogasawara, M.; Matsubara, T.; Suzuki, H. Biol. Pharm. Bull. 2001, 24, 720; Ogasawara, M.; Matsubara, T.; Suzuki, H. Biol. Pharm. Bull. 2001, 24, 917; Ogasawara, M.; Matsunaga, T.; Takahashi, S.; Saiki, I.; Suzuki, H. Biol. Pharm. Bull. 2002, 25, 1491. Evodiamine is commercially available from Wako Pharmaceuticals.
36. A screening approach revealed the natural product evodiamine as a potent anti-invasive and anti-metastatic agent: Ogasawara, M.; Matsubara, T.; Suzuki, H. Biol. Pharm. Bull. 2001, 24, 720; Ogasawara, M.; Matsubara, T.; Suzuki, H. Biol. Pharm. Bull. 2001, 24, 917; Ogasawara, M.; Matsunaga, T.; Takahashi, S.; Saiki, I.; Suzuki, H. Biol. Pharm. Bull. 2002, 25, 1491. Evodiamine is commercially available from Wako Pharmaceuticals.
37. A screening approach revealed the natural product evodiamine as a potent anti-invasive and anti-metastatic agent: Ogasawara, M.; Matsubara, T.; Suzuki, H. Biol. Pharm. Bull. 2001, 24, 720; Ogasawara, M.; Matsubara, T.; Suzuki, H. Biol. Pharm. Bull. 2001, 24, 917; Ogasawara, M.; Matsunaga, T.; Takahashi, S.; Saiki, I.; Suzuki, H. Biol. Pharm. Bull. 2002, 25, 1491. Evodiamine is commercially available from Wako Pharmaceuticals.