Synthesis of novel brassinosteroid biosynthesis inhibitors based on the ketoconazole scaffold

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 4, 2012, Pages 1625-1628

  Oh, Keimei ^a   Yamada, Kazuhiro ^a   Asami, Tadao ^b   Yoshizawa, Yuko ^a  

^a AKITA PREFECTURAL UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

Brassinosteroid biosynthesis inhibitor; Plant hormone; Triazole derivatives

Indexed keywords

1 [2 (4 CHLOROPHENYL) 4 [2 (2 ETHOXYPHENYL)ETHYL] 1,3 DIOXOLAN 2 YLMETHYL] 1H 1,2,4 TRIAZOLE; BRASSINOLIDE; BRASSINOSTEROID; GIBBERELLIN; KETOCONAZOLE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARABIDOPSIS; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DWARFISM; HORMONE SYNTHESIS; IC 50; PLANT GROWTH; PLANT SEED; STEM ELONGATION; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ARABIDOPSIS;

EID: 84856681904     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.12.120     Document Type: Article

References (30)

1. Clouse, S. D.; Sasse, J. M. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1998, 49, 427.
2. Sasse, J. J. Plant Growth Regul. 2003, 22, 276.
3. Krishna, P. J. Plant Growth Regul. 2003, 22, 289.
4. Choe, S.; Dilkes, B. P.; Gregory, B. D.; Ross, A. S.; Yuan, H.; Noguchi, T.; Fujioka, S.; Takatsuto, S.; Tanaka, A.; Yoshida, S.; Tax, F. E.; Feldmann, K. A. Plant Physiol. 1999, 119, 897.
5. Bishop, G. J.; Nomura, T.; Yokota, T.; Harrison, K.; Noguchi, T.; Fujioka, S.; Takatsuto, S.; Jones, J. D.; Kamiya, Y. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 1761.
6. Hong, Z.; Ueguchi-Tanaka, M.; Umemura, K.; Uozu, S.; Fujioka, S.; Takatsuto, S.; Yoshida, S.; Ashikari, M.; Kitano, H.; Matsuoka, M. Plant Cell 2003, 15, 2900.
7. Nomura, T.; Nakayama, M.; Reid, J. B.; Takeuchi, Y.; Yokota, T. Plant Physiol. 1997, 113, 31.
8. Wu, C. Y.; Trieu, A.; Radhakrishnan, P.; Kwok, S. F.; Harris, S.; Zhang, K.; Wang, J.; Wan, J.; Zhai, H.; Takatsuto, S.; Matsumoto, S.; Fujioka, S.; Feldmann, K. A.; Pennell, R. Plant Cell 2008, 20, 2130.
9. Sakamoto, T.; Morinaka, Y.; Ohnishi, T.; Sunohara, H.; Fujioka, S.; Ueguchi- Tanaka, M.; Mizutani, M.; Sakata, K.; Takatsuto, S.; Yoshida, S.; Tanaka, H.; Kitano, H.; Matsuoka, M. Nat. Biotechnol. 2006, 24, 105.
10. Fujioka, S.; Sakurai, A. Physiologia Plantarum 1997, 100, 710.
11. Mathur, J.; Molnár, G.; Fujioka, S.; Takatsuto, S.; Sakurai, A.; Yokota, T.; Adam, G.; Voigt, B.; Nagy, F.; Maas, C.; Schell, J.; Koncz, C.; Szekeres, M. Plant J. 1998, 14, 593.
12. Kim, T. W.; Chang, S. C.; Lee, J. S.; Hwang, B.; Takatsuto, S.; Yokota, T.; Kim, S. K. Phytochemistry 2004, 65, 679.
13. Kim, T. W.; Hwang, J. Y.; Kim, Y. S.; Joo, S. H.; Chang, S. C.; Lee, J. S.; Takatsuto, S.; Kim, S. K. Plant Cell 2005, 17, 2397.
14. Testa, B.; Jenner, P. Drug Metab. Rev. 1981, 12, 1.
15. Rogerson, T. D.; Wilkinson, C. F.; Hetarski, K. Biochem. Pharmacol. 1977, 26, 1039.
16. Oh, K. Regul. Plant Growth Dev. 2009, 44, 166.
17. Oh, K.; Murofushi, N. Bioorg. Med. Chem. 2002, 10, 3707.
18. Oh, K.; Seki, Y.; Murofushi, N.; Yoshizawa, Y. Pestic. Biochem. Physiol. 2009, 94, 107.
19. Oh, K.; Asami, T.; Matsui, K.; Howe, G. A.; Murofushi, N. FEBS Lett. 2006, 580, 5791.
20. Min, Y. K.; Asami, T.; Fujioka, S.; Murofushi, N.; Yamaguchi, I.; Yoshida, S. Bioorg. Med. Chem. Lett. 1999, 9, 425.
21. Sekimata, K.; Ohnishi, T.; Mizutani, M.; Todoroki, Y.; Han, S. Y.; Uzawa, J.; Fujioka, S.; Yoneyama, K.; Takeuchi, Y.; Takatsuto, S.; Sakata, K.; Yoshida, S.; Asami, T. Biosci., Biotechnol., Biochem. 2008, 72, 7.
22. Sekimata, K.; Han, S. Y.; Yoneyama, K.; Takeuchi, Y.; Yoshida, S.; Asami, T. J. Agri. Food Chem. 2002, 50, 3486.
23. Sekimata, K.; Uzawa, J.; Han, S. Y.; Yoneyama, K.; Takeuchi, Y.; Yoshida, S.; Asami, T. Tetrahedron: Asymmetry 2002, 13, 1875.
24. Asami, T.; Mizutani, M.; Fujioka, S.; Goda, H.; Min, Y. K.; Shimada, Y.; Nakano, T.; Takatsuto, S.; Matsuyama, T.; Nagata, N.; Sakata, K.; Yoshida, S. J. Biol. Chem. 2001, 276, 25687.
25. Asami, T.; Min, Y. K.; Nagata, N.; Yamagishi, K.; Takatsuto, S.; Fujioka, S.; Murofushi, N.; Yamaguchi, I.; Yoshida, S. Plant Physiol. 2000, 123, 93.
26. Oh, K.; Shimura, Y.; Ishikawa, K.; Ito, Y.; Asami, T.; Murofushi, N.; Yoshizawa, Y. Bioorg. Med. Chem. 2008, 16, 1090.
27. Scheinfeld, N. Drugs Today 2008, 44, 369.
28. Tanoury, G. J.; Hett, R.; Wilkinson, H. S.; Wald, S. A.; Senanayake, C. H. Tetrahedron: Asymmetry 2003, 14, 3487.
29. Tanoury, G. J.; Senanayake, C. H.; Hett, R.; Kuhn, A. M.; Kessler, D. W.; Wald, S. A. Tetrahedron Lett. 1998, 39, 6845.
30. Wang, Z. Y.; Nakano, T.; Gendron, J.; He, J.; Chen, M.; Vafeados, D.; Yang, Y.; Fujioka, S.; Yoshida, S.; Asami, T.; Chory, J. Dev. Cell 2002, 2, 505.