New efficient synthesis of resorcinylic macrolides via ynolides: Establishment of cycloproparadicicol as synthetically feasible preclinical anticancer agent based on Hsp90 as the target

Journal of the American Chemical Society

Volumn 126, Issue 25, 2004, Pages 7881-7889

  Yang, Zhi Qiang ^a   Geng, Xudong ^a   Solit, David ^a   Pratilas, Christine A ^a   Rosen, Neal ^a   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

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

Author keywords

[No Author keywords available]

Indexed keywords

COBALT; PROTEINS; SYNTHESIS (CHEMICAL); TUMORS;

ANTICANCER AGENTS; RING CLOSING METATHESIS (RCM);

DRUG PRODUCTS;

5,5 DIMETHYL 1,3 CYCLOHEXANEDIONE; AIGIALOMYCIN D; ALKADIENE; ANTINEOPLASTIC AGENT; BISSILOXYDIENE; CHAPERONE; COBALT COMPLEX; CYCLOPROPARADICICOL; EPIDERMAL GROWTH FACTOR RECEPTOR 2; HEAT SHOCK PROTEIN 90; MACROLIDE; NEU DIFFERENTIATION FACTOR; ONCOPROTEIN; PROTEIN; RADICICOL; RESORCINYLIC MACROLIDE DERIVATIVE; UNCLASSIFIED DRUG; YNOLIDE;

ANTINEOPLASTIC ACTIVITY; AROMATIZATION; ARTICLE; CELL GROWTH; COMPLEX FORMATION; CONTROLLED STUDY; CYCLIZATION; CYCLOADDITION; CYTOTOXICITY; DIELS ALDER REACTION; DRUG POTENCY; DRUG STRUCTURE; GROWTH INHIBITION; HUMAN; HUMAN CELL; MACROCYCLIZATION; PROTEIN DEGRADATION; RING CLOSING METATHESIS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CELL LINE, TUMOR; COBALT; CYCLOPROPANES; HSP90 HEAT-SHOCK PROTEINS; HUMANS; INHIBITORY CONCENTRATION 50; LACTONES; MACROLIDES; MOLECULAR CHAPERONES; MOLECULAR STRUCTURE; RESORCINOLS;

EID: 3042685847     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0484348     Document Type: Article

References (60)

1. Banerji, U.; Judson, I.; Workman, P. Curr. Cancer Drug Targets 2003, 3, 385-390.
2. Delmotte, P.; Delmotte-Plaquee, J. Nature 1953, 171, 344.
3. Ayer, W. A.; Lee, S. P.; Tsuneda, A.; Hiratsuka, Y. Can. J. Microbiol. 1980, 26, 766-773.
4. Roe, S. M.; Prodromou, C.; O'Brien, R.; Ladbury, J. E.; Piper, P. W.; Pearl, L. H. J. Med. Chem. 1999, 42, 260-266.
5. DeBoer, C.; Meulman, P. A.; Wnuk, R. J.; Peterson, D. H. J. Antibiot. 1970, 23, 442-447.
6. Kuduk, S. D.; Harris, C. R.; Zheng, F. F.; Sepp-Lorenzino, L.; Ouerfelli, O.; Rosen, N.; Danishefsky, S. J. Bioorg. Med. Chem. Lett. 2000, 10, 1303-1306.
7. Zheng, F. F.; Kuduk, S. D.; Chiosis, G.; Munster, P. N.; Sepp-Lorenzino, L.; Danishefsky, S. J.; Rosen, N. Cancer Res. 2000, 60, 2090-2094.
8. Kuduk, S. D.; Zheng, F. F.; Sepp-Lorenzino, L.; Rosen, N.; Danishefsky, S. J. Bioorg. Med. Chem. Lett. 1999, 9, 1233-1238.
9. Chiosis, G.; Lucas, B.; Huezo, H.; Solit, D.; Basso, A.; Rosen, N. Curr. Cancer Drug Targets 2003, 3, 371-376.
10. Agatsuma, T.; Ogawa, H.; Akasaka, K.; Asai, A.; Yamashita, Y.; Mizukami, T.; Akinaga, S.; Saitoh, Y. Bioorg. Med. Chem. 2002, 10, 3445-3454.
11. Yamamoto, K.; Garbaccio, R. M.; Stachel, S. J.; Solit, D. B.; Chiosis, G.; Rosen, N.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 1280-1284.
12. Yang. Z.-Q.; Danishefsky, S. J. J. Am. Chem. Soc. 2003, 125, 9602-9603.
13. Gen, X.; Danishefsky, S. J. Org. Lett. 2004, 6, 413-416.
14. Danishefsky, S.; Etheredge, S. J. J. Org. Chem. 1979, 44, 4716-4717.
15. Friedrich, L. E.; De Vera, N.; Hamilton, M. Synth. Commum. 1980, 10. 637-643.
16. Barrett, A. G. M.; Pena, M.; Willardsen, J. A. J. Org. Chem. 1996, 61. 1082-1100.
17. Fuganti, C.; Pedrocchi-Fantoni, G.; Sarra, A.; Servi, S. Tetrahedron: Asymmetry 1994, 5, 1135-1138.
18. Garbaccio, R. M.; Stachel, S. J.; Baeschlin, D. K.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 10903-10908.
19. Romo, D.; Rzasa, R. M.; Shea, H. A.; Park, K.; Langenhan, J. M.; Sun, L.; Akhiezer, A.; Liu, J. O. J. Am. Chem. Soc. 1998, 120, 12237-12254.
20. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
21. Kinoshita, A.; Mori, M. Synlett 1994, 1020-1022.
22. Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356-8357.
23. Mori, M.; Sakakibara, N.; Kinoshita, A. J. Org. Chem. 1998, 63, 6082-6083.
24. Greenfield, H.; Sternberg, H. W.; Friedel, R. A.; Wotiz, J. H.; Markby, R.; Wender, I. J. Am. Chem. Soc. 1956, 78, 120-124.
25. Nicholas, K. M.; Pettit, R. Tetrahedron Lett. 1971, 37, 3475-3478.
26. Dickson, R. S.; Fraser, P. J. Adv. Organomet. Chem. 1974, 12, 323-377.
27. Recently, a similar protocol was reported: Young, D. G. J.; Burlison, J. A.; Peters, U. J. Org. Chem. 2003, 68, 3494-3497.
28. Magnus, P. Tetrahedron 1994, 50, 1397-1418.
29. Tanaka, S.; Tsukiyama, T.; Isobe, M. Tetrahedron Lett. 1993, 34, 5757-5760.
30. Jones, G. B.; Wright, J. M.; Rush, T. M.; Plourde, G. W., II.; Kelton, T. F.; Mathews, J. E.; Huber, R. S.; Davidson, J. P. J. Org. Chem. 1997, 62, 9379-9381.
31. Magnus, P.; Eisenbeis, S. A.; Fairhurst, R. A.; Iliadis, T.; Magnus, N. A.; Parry, D. J. Am. Chem. Soc. 1997, 119, 5591-5605.
32. Yamamoto, K.; Suzuki, S.; Tsuji, J. Chem. Lett. 1978, 649-652.
33. Banville, J.; Brassard, P. J. Chem. Soc., Perkin Trans. 11976, 1852-1856.
34. Danishefsky, S.; Singh, R. K.; Gammill, R. B. J. Org. Chem. 1978, 43, 379-380.
35. Danishefsky, S.; Harvey, D. F.; Quallich, G.; Uang, B. J. J. Org. Chem. 1984, 49, 392-393.
36. Castellino, S.; Sims, J. J. Tetrahedron Lett. 1984, 25, 2307-2310.
37. Lopez, R.; Carretero, J. C. Tetrahedron: Asymmetry, 1991, 2, 93-96.
38. Ibuka, T.; Mori, Y.; Aoyama, T.; Inubushi, Y. Chem. Pharm. Bull. 1978, 26, 456-465.
39. Langer, P.; Schneider, T.; Stoll, M. Chem. Eur. J. 2000, 6, 3204-3214.
40. Uchiyama, M.; Kimura, Y.; Ohta, A. Tetrahedron Lett. 2000, 41, 10013-10017.
41. Morrison, C. F.; Burnell, D. J. Tetrahedron Lett. 2001, 42, 7367-7369.
42. Gritter, R. J.; Wallace, T. J. J. Org. Chem. 1959, 24, 1051-1056.
43. Trost, B. M.; Caldwell, C. G.; Murayama, E.; Heissler, D. J. Org. Chem. 1983, 48, 3252-3265.
44. Huang, S. L.; Omura, K.; Swern, D. J. Org. Chem. 1976, 41, 3329-3231.
45. Hauser, F. M.; Prasanna, S.; Combs, D. W. J. Org. Chem. 1983, 48, 1328-1333.
46. Welch, S. C.; Levine, J. A.; Arimilli, M. N. Synth. Commun. 1993, 23, 131-134.
47. Tatsuta, K.; Takano, S.; Sato, T.; Nakano, S. Chem. Lett. 2001, 172-173.
48. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666.
49. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Org. Chem. 1991, 56, 1296-1298.
50. Elix, J. A.; Barclay, C. E.; Lumbsch, H. T.; Wardlaw, J. H. Aust. J. Chem. 1997, 50, 971-975.
51. Elix, J. A.; Crook, C. E.; Hui, J.; Zhu, Z. N. Aust. J. Chem. 1992, 45, 845-855.
52. Tanis, S. P.; Robinson, E. D.; McMills, M. C.; Watt, W. J. Am. Chem. Soc. 1992, 114, 8349-8362.
53. Chou, T.-C.; Dong, H.; Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Tong, W. P.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 4762-4767.
54. Tian, F.; Kruger, V.; Bautista, O.; Duan, J.-X.; Li, A.-R.; Dolbier, W. R., Jr.; Chen, Q.-Y. Org. Lett. 2000, 2, 563-564.
55. Stachel, S. J.; Lee, C. B.; Spassova, M.; Chappell, M. D.; Bornmann, W. G.; Danishefsky, S. J.; Chou, T. C.; Guan, Y. J. Org. Chem. 2001, 66, 4369-4378.
56. Mitsunobu, O. Synthesis 1981, 1-28.
57. Thompson, A. S.; Humphrey, G. R.; DeMarco, A. M.; Mathre, D. J.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 5886-5888.
58. Kurosawa, W.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2003, 125, 8112-8113.
59. Isaka, M.; Suyarnsestakorn, C.; Tanticharoen, M.; Kongsaeree, P.; Thebtaranonth, Y. J. Org. Chem. 2002, 67, 1561-1566.
60. Martin, J. C.; Arhart, R. J. J. Am. Chem, Soc. 1971, 93, 4327-4329.