Chemical study on hapalosin, a cyclic depsipeptide possessing multidrug resistance reversing activities: Synthesis, structure and biological activity

Tetrahedron

Volumn 52, Issue 47, 1996, Pages 14723-14734

  Okuno, Toshiaki ^a   Ohmori, Ken ^a   Nishiyama, Shigeru ^d   Yamamura, Shosuke ^d   Nakamura, Kensuke ^b   Houk, K N ^b   Okamoto, Kazuya ^c  

^a KEIO UNIVERSITY   (Japan)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c NIPPON KAYAKU CO LTD   (Japan)

^d NONE

Author keywords

[No Author keywords available]

Indexed keywords

DEPSIPEPTIDE; DOXORUBICIN; HAPALOSIN; UNCLASSIFIED DRUG; VERAPAMIL;

ARTICLE; BREAST CANCER; CELL LINE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOLECULAR MODEL; MULTIDRUG RESISTANCE; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; TUMOR CELL;

EID: 0030592790     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00951-9     Document Type: Article

References (28)

1. 1. Preliminary communication: Ohmori, K.; Okuno, T.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 3467-3470.
2. 2. Simon, S. M.; Schinller, M. Proc. Natl. Acad. Sci. U. S. A. 1994, 91, 3497-3504.
3. 3. a) Pearce, H. L.; Safa, A. R.; Bach, N. J.; Winter, M. A.; Cirtain, M. C.; Beck, W. T. Natl. Acad. Sci. U. S. A. 1989, 86, 5128-5132.
4. b) Beck, W. T.; Cirtain, M. C.; Glover, C. J.; Felsted, R. L.; Safa, A. R. Biochem. Biophys. Res. Commun. 1988, 153, 959-966.
5. c) Cornwell, M. M.; Pastan, I.; Gottesman, M. M. J. Biol. Chem. 1987, 262, 2166-2170.
6. d) Tsuruo, T.; Iida, H.; Tsukagoshi, S.; Sakurai, Y. Cancer Res. 1981, 41, 1967-1972.
7. e) Fojo, A.; Akiyama, S.-I.; Gottesman, M. M.; Pastan, I. Cancer Res. 1985, 45, 3002-3007.
8. f) Cornwell, M. M.; Safa, A. R.; Felsted, R. L.; Gttesman, M. M.; Pastan, I. Natl. Acad. Sci. U. S. A. 1986, 83, 3847-3850.
9. g) Beck, W. T.; Cirtain, M.; Look, A. T.; Ashum, R. A. Cancer Res. 1986, 46, 778-784.
10. h) Dellinger, M.; Pressman, B. C.; Calderon-Higginson, C.; Savaraj, N.; Tapiero, H.; Kolonias, D.; Lampidis, T. J. Cancer Res., 1992, 52, 6385-6389.
11. i) Niwa, K.; Yamada, K.; Furukawa, T.; Shudo, N.; Seto, K.; Matsumoto, T. Takao, S.; Akiyama, S.; Shimazu, H. Cancer Res., 1992, 52, 3655-3660.
12. 4. Stratmann, K.; Burgoyne, D. L.; Moore, R. E.; Patterson, G. M. L. J. Org. Chem., 1994, 59, 7219 -7226.
13. 5. Three groups independently reported synthesis of 1. a) Dinh, T. Q.; Armstrong, R. W. J. Org. Chem. 1995, 60, 8118-8119.
14. b) Ghosh, A. K.; Liu, W.; Xu, Y.; Chen, Z. Angew. Chem. Int. Ed. Engl. 1996, 35, 74-76.
15. c) Wagner, B.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1996, 37, 6557-6560. After submission of this paper, a similar study including synthesis of 11 and computational modeling has been published: Dinh, T. Q.; Du, X.; Armstrong, R. W. J. Org. Chem. 1996, 61, 6606-6616.
16. c) Wagner, B.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1996, 37, 6557-6560. After submission of this paper, a similar study including synthesis of 11 and computational modeling has been published: Dinh, T. Q.; Du, X.; Armstrong, R. W. J. Org. Chem. 1996, 61, 6606-6616.
17. 6. Ager, D. A.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. Many references cited therein.
18. 7. Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129.
19. 8. a) Maibaum, J.; Rich, D. H. J. Org. Chem. 1988, 53, 869-873.
20. b) Parkes, K. E. B.; Bushnell, D. J.; Crackett, P. H.; Dunsdon, S. J.; Freeman, A. C.; Gunn, M. P.; Hopkins, R. A.; Lambert, R. W.; Martin, J. A.; Merrett, J. H.; Redshaw, S.; Spurden, W. C.; Thomas, G. J. J. Org. Chem. 1994, 59, 3656-3664.
21. 9. Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. Tetrahedron Lett. 1994, 35, 7171-7172.
22. 10. Abstraction of the siloxy group was unsucessful under TBAF conditions, which resulted in an inseparable mixture.
23. 11. Shioiri, T.; Hayashi, K.; Hamada, Y. Tetrahedron 1993, 49, 1913-1924.
24. 12. The same observation was reported by Armstrong (see ref.5a).
25. 13. a) MACROMODEL 4.5; W. C. Still, Columbia University: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R. M. J.; Lipton, M. A.; Caufield, C. E.; Chang, G.; Hendrickson, T. F.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
26. b) Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127: Burkert, U.; Allinger, N, L. ACS Monograph 177, Americal Chemical Society, Washington D. C., 1982.
27. b) Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127: Burkert, U.; Allinger, N, L. ACS Monograph 177, Americal Chemical Society, Washington D. C., 1982.
28. 14. Mori, K. Tetrahedron 1976, 32, 1101-1106.