Design and synthesis of curacin a analogs with varied side chain structures

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 20, 1997, Pages 2657-2660

  Nishikawa, Asuka ^a   Shirai, Ryuichi ^a   Koiso, Yukiko ^a   Hashimoto, Yuichi ^a   Iwasaki, Shigeo ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMITOTIC AGENT;

ARTICLE; CYANOBACTERIUM; CYTOTOXICITY; DRUG ACTIVITY; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; MICROTUBULE ASSEMBLY; STEREOISOMERISM;

EID: 0030721459     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10055-5     Document Type: Article

References (14)

1. (a). Dustin, P., Microtubules, Springer-Verlag, New York, 1978.
2. (b). Soifen, D., 45d., Dynamic Aspects of Microtubule Biology, New York Academy of Science, New York, 1986.
3. Avila, J., Ed., Microtubule Proteins, CRC, Boca Raton, FL, 1990.
4. Hamel, E., in Microtubule Proteins, Avila, J., Ed., CRC, Boca Raton, FL, 1990.
5. Iwasaki, S. Med. Res. Rev. 1993,13, 183-198.
6. Gerwick, W. H.; Proteau, P. J.; Nagle, D. G.; Hamel, E.; Blokhin, A.; Slate, D. L. J. Org. Chem. 1994, 59, 1243-1245.
7. (a). Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett. 1995, 36, 5765-5768.
8. (b). Onoda, T.; Shirai, R.; Koiso, Y.; Iwasaki, S. Tetrahedron Lett., 1996, 37, 4397-4400.
9. Onoda, T.; Shirai, R.; Kawai, K.; Iwasaki, S. Tetrahedron, 1996, 52, 13327-13338.
10. Onoda, T.; Shirai, R.; Koiso, Y; Iwasaki, S. Tetrahedron, 1996, 52, 14543-14562.
11. (e). Onoda, T.; Shirai, R.; Iwasaki, S. Tetrahedron Lett., 1997, 38, 1443-1446.
12. Blokhin. A. V.; Yoo, H. -D.; Geralds, R. S.; Nagle, D. G.; Gerwick, W. H.; Hamel, E. Mol. Pharmacol., 1995, 48, 523-531.
13. In our total synthesis of curacin A, isomeric E olefin could not be detected. See references 4.
14. Takahashi, M.; Iwasaki, S.; Kobayashi, H.; Okuda, S.; Murai, T.; Sato, Y.; Haraguchi-Hiraoka, T.; Nagano, H. J. Antibiotics, 1987, 40, 66-72.