Design of scytalone dehydratase inhibitors as rice blast fungicides: (N- phenoxypropyl)-carboxamides

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 11, 1999, Pages 1607-1612

  Jordan, Douglas B ^a   Lessen, Thomas A ^a   Wawrzak, Zdzislaw ^a   Bisaha, John J ^a   Gehret, Troy C ^a   Hansen, Stephen L ^a   Schwartz, Rand S ^a   Basarab, Gregory S ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; FUNGICIDE; HYDROLYASE INHIBITOR; SCYTALONE DEHYDRATASE INHIBITOR; UNCLASSIFIED DRUG;

AGRICULTURE; ARTICLE; CELL WALL; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; MELANOGENESIS; MYCOSIS;

ANTIFUNGAL AGENTS; CRYSTALLOGRAPHY, X-RAY; CYCLOPROPANES; DRUG DESIGN; HYDRO-LYASES; KINETICS; MODELS, CHEMICAL; MODELS, MOLECULAR; PLANT DISEASES; TYRPHOSTINS;

EID: 0033532716     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00246-2     Document Type: Article

References (21)

1. Present address: Northwestern University, DND-CAT, 9700 S. Cass Ave., Argonne, IL 60439.
2. Present address: E. I. DuPont de Nemours Life Sciences, Bldg. 328, Experimental Station, Wilmington DE 19880-0328.
3. Howard, R. J.; Ferrari, M. A. Exp. Mycol. 1989, 13, 403.
4. Bell, A. A; Wheeler, M. H. Annu. Rev. Phytophath. 1986, 24, 411.
5. Chumley, F. G.; Valent, B. Mol. Plant-microbe Interact. 1990, 3, 135.
6. Kurahashi, Y.; Sakawa, S.; Kinbara, T.; Tanaka, K.; Kagabu, S. J. Pesticide Sci. 1997, 22, 108.
7. Agrow, PJP Publications Ltd., UK, 1997, vol. 287, pp. 21-22.
8. Lundqvist, T.; Weber, P. C.; Hodge, C. N.; Braswell, E. H.; Rice, J.; Pierce, J. J. Mol. Biol. 1993, 232, 999.
9. Lundqvist, T.; Rice, J.; Hodge, C. N.; Basarab, G. S.; Pierce, J.; and Lindqvist, Y. Structure (London) 1994, 2, 937.
10. Basarab, G. S.; Steffens, J. J.; Lundqvist, T.; Wawrzak, Z., Schwartz, R. S.; Jordan, D. B. Biochemistry 1999, 38, in press.
11. Wawrzak, Z.; Sandalova, T.; Steffens, J. J.; Basarab, G. S.; Lundqvist, T., Lindqvist, Y.; Jordan, D. B. Proteins: Struct., Funct. Genet. 1999, 33, in press.
12. Nakasako, M.; Motoyama, T.; Kurahashi, Y.; Yamaguchi, I. Biochemistry 1998, 37, 9931.
13. Chen, J. M.; Xu, S. L.; Wawrzak, Z.; Basarab, G. S.; Jordan, D. B. Biochemistry 1998, 37, 17735.
14. Optimizations were run using the Tripos (St. Louis, MO) molecular mechanics force field with the residues and water molecules lying within 8 Å of the inhibitor. The Powell gradient, Gasteiger-Hückel charges, non-bonded cutoffs of 8 Å and a distance dialectric constant of 1.0 were used.
15. Grote, C. W.; Kim, D. J.; Rapoport, H. J. Org. Chem. 1995, 60, 6987.
16. Kraatz, U.; Hänssler, G. DE 88-3815728, 1988 Chem. Abst. 1990, 113, 23390.
17. Schawmann, E.; Mrotzek, H. Tetrahedron 1979, 35, 1965.
18. Basarab, G. S.; Hansen, S. L; Jordan, D. B.; Lessen, T. A. PCT. Int. Appl. WO 9833765 A1, 1998; Chem. Abstr. 1998, 129, 175444.
19. Gomez, J.; Freire, E. J. Mol. Biol. 1995, 252, 337.
20. Details of the X-ray structure will be presented elsewhere.
21. Bromilow, R. H.; Chamberlain, K. Monogr. - Br. Plant Growth Regul. Group 1989, 18, 113.