Synthesis of intervenolin, an antitumor natural quinolone with unusual substituents

Organic Letters

Volumn 15, Issue 9, 2013, Pages 2124-2127

  Abe, Hikaru ^a   Kawada, Manabu ^b   Inoue, Hiroyuki ^b   Ohba, Shun Ichi ^b   Nomoto, Akio ^a   Watanabe, Takumi ^a   Shibasaki, Masakatsu ^a  

^a INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

^b Institute of Microbial Chemistry (BIKAKEN)   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; BIOLOGICAL PRODUCT; INTERVENOLIN; ISOTHIOCYANIC ACID DERIVATIVE; QUINOLONE DERIVATIVE;

ANIMAL; ARTICLE; CHEMISTRY; DRUG EFFECT; HUMAN; MOUSE; PATHOLOGY; STROMA CELL; SYNTHESIS; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; BIOLOGICAL AGENTS; CELL LINE, TUMOR; HUMANS; ISOTHIOCYANATES; MICE; QUINOLONES; STROMAL CELLS;

EID: 84877107839     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400587a     Document Type: Article

References (40)

1. Wernert, N. Virchows. Arch. 1997, 430, 433
2. Tuxhorn, J. A.; Ayala, G. E.; Smith, M. J.; Smith, V. C.; Dang, T. D.; Rowley, D. R. Clin. Cancer Res. 2002, 8, 2912
3. Wiseman, B. S.; Werb, Z. Science 2002, 296, 1046
4. Hwang, R. F.; Moore, T.; Arumugam, T.; Ramachandran, V.; Amos, K. D.; Rivera, A.; Ji, B.; Evans, D. B.; Logsdon, C. D. Cancer Res. 2008, 68, 918
5. Picard, O.; Rolland, Y.; Poupon, M. F. Cancer Res. 1986, 46, 3290
6. Camps, J. L.; Chang, S. M.; Hsu, T. C.; Freeman, M. R.; Hong, S. J.; Zhau, H. E.; von Eschenbach, A. C.; Chung, L. W. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 75
7. Kawada, M.; Yoshimoto, Y.; Minamiguchi, K.; Kumagai, H.; Someno, T.; Masuda, T.; Ishizuka, M.; Ikeda, D. A Anticancer Res. 2004, 24, 1561
8. Kawada, M.; Inoue, H.; Masuda, T.; Ikeda, D. Cancer Res. 2006, 66, 4419
9. Kawada, M.; Inoue, H.; Usami, I.; Ikeda, D. Cancer Sci. 2009, 100, 150
10. Kawada, M.; Momose, I.; Someno, T.; Tsujiuchi, G.; Ikeda, D. J. Antibiot. 2009, 62, 243
11. Kawada, M.; Someno, T.; Inoue, H.; Ohba, S.-i.; Masuda, T.; Kato, T.; Ikeda J. Antibiot. 2010, 63, 319
12. Kawada, M.; Inoue, H.; Ohba, S.-i.; Masuda, T.; Momose, I.; Ikeda, D. Int. J. Cancer 2010, 126, 810
13. Kawada, M.; Inoue, H.; Ohba, S.-i.; Hatano, M.; Amemiya, M.; Hayashi, C.; Usami, I.; Abe, H.; Watanabe, T.; Kinoshita, N.; Igarashi, M.; Masuda, T.; Ikeda, D.; Nomoto, A. J. Antibiot. in press.
14. Ahmed, A.; Daneshtalab, M. J. Pharm. Pharmaceut. Sci. 2012, 15, 52
15. Drlica, K.; Malik, M.; Kerns, R. J.; Zhaol, X. Antimicrob. Agents Chemother. 2008, 52, 385
16. Nishizawa, T.; Suzuki, H.; Hibi, T. J. Clin. Biochem. Nutr. 2009, 44, 119
17. Richter, S.; Parolin, C.; Palumbo, M.; Palo, G. Curr. Drug Targets: Infect. Disord. 2004, 4, 111
18. Sissi, C.; Palumbo, M. Curr. Med. Chem.: Anti-Cancer Agents 2003, 3, 439
19. Wiles, J. A.; Bradbury, B. J.; Pucci, M. J. Exp. Opin. Ther. Pat. 2010, 20, 1295
20. Hoppe, D.; Beckmann, L. Liebigs Ann. Chem. 1979, 2066
21. Oppolzer, W.; Moretti, R.; Thomi, S. Tetrahedron Lett. 1989, 30, 6009
22. Ikegami, S.; Hayama, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 3403
23. Ikegami, S.; Uchiyama, H.; Hayama, T.; Katsuki, T.; Yamaguchi, M. Tetrahedron 1988, 44, 5533
24. Oppolzer, W.; Moretti, R.; Zhou, C. Helv. Chim. Acta 1994, 77, 2363
25. Ueda, M.; Yamamura, S. Tetrahedron Lett. 1999, 40, 353
26. Ueda, M.; Yamamura, S. Tetrahedron 1999, 55, 10937
27. Schantl, J. G.; Türk, W. Heterocycles 1984, 22, 2595
28. Chung, N. M.; Tieckelmann, H. J. Org. Chem. 1970, 35, 2517
29. Liu, H.; Ko, S.-B.; Josien, H.; Curran, D. P. Tetrahedron Lett. 1995, 36, 8917
30. Breugst, M.; Mayr, H. J. Am. Chem. Soc. 2010, 132, 15380
31. Fang, Y.-Q.; Bio, M. M.; Hansen, K. B.; Potter, M. S.; Clausen, A. J. Am. Chem. Soc. 2010, 132, 15525
32. Dekker, K. A.; Inagaki, T.; Gootz, T. D.; Huang, L. H.; Kojima, Y.; Kohlbrenner, W. E.; Matsunaga, Y.; McGuirk, P. R.; Nomura, E.; Sakakibara, T.; Sakemi, S.; Suzuki, Y.; Yamauchi, Y.; Kojima, N. J. Antibiot. 1998, 51, 145
33. Brown, M. F. Eur. Pat. Appl. 811613, 1997.
34. Kiely, J. S.; Huang, S.; Lesheski, L. E. J. Heterocycl. Chem. 1989, 26, 1675
35. Camps, R. Chem. Ber 1899, 32, 3228
36. Pflum, D. A. Camps Quinolinol Synthesis. In Name Reactions in Heterocyclic Chemistry; Li, J. J.; Corey, E. J., Eds.; Wiley-Interscience: Hoboken, NJ, 2005; pp 386.
37. Krapcho, A. P.; Stephens, W. P. J. Org. Chem. 1980, 45, 1106
38. Zewege, D.; Chen, C.-y.; Deer, C.; Dormer, P. G.; Hughes, D. L. J. Org. Chem. 2007, 72, 4276
39. Dutheuil, G.; Selander, N.; Szabó, K. J.; Aggarwal, V. K. Synthesis 2008, 2293
40. Smith, P. A. S.; Emerson, D. W. J. Am. Chem. Soc. 1960, 82, 3076