Synthesis and antifungal activities of furoxan derivatives designed as novel fungicide

Bioscience, Biotechnology and Biochemistry

Volumn 62, Issue 9, 1998, Pages 1693-1697

  Hwang, Kwang Jin ^a   Park, Young C ^a   Kim, Hyung Jin ^b   Lee, Jae Hyun ^c  

^a Hongik University   (Japan)

^b Chonnam National University   (South Korea)

^c Korea Research Institute of Chemical Technology   (South Korea)

Author keywords

Fungicidal activity; Furazan N oxide; Furoxan; Wheat leaf rust

Indexed keywords

EID: 0001548894     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.62.1693     Document Type: Article

References (16)

1. Feelisch, M., The biochemical Pathways of nitric oxide formation from nitrovasodilators: Appropriate choice of exogenous NO donors and aspects of preparation and handling of aqueous NO solutions. J. Cardiovasc. Pharmacol., 17, S25-S33 (1991).
2. Feelisch M., Schonafinger, K., and Noack, E., Thiol-mediated generation of nitric oxide accounts for the vasodilator action of furox-ans. Biochem. Pharmacol., 44, 1149-1157 (1992).
3. Calvino, R., Fruttero, R., Ghigo, D., Bosia, A., Pescarmona, G. P., and Gasco, A., 4-Methyl-3-(arylsufonyl)furoxans: A new class of potent inhibitors of platelet aggregation. J. Med. Chem., 35, 3296-3300 (1992).
4. Ghigo, D., Heller, R., Calvino, R., Allessio, P., Fruttero, R., Gasco, A., Bosia, A., and Pescarmona, G. P., Characterization of a new compound, S35b, as a guany-late cyclase activator in human platelets. Biochem. Pharmacol., 43, 1281-1238 (1992).
5. Sexton, D. J., Muruganandam, A., Mckenney, D. J., and Mutus, B., Visible light photochemical release of nitric oxide from S-nitrosoglutathione: Potential photochemotherapeutic applications. Photochem. Photobiol., 59, 463-467 (1994).
6. Nathan, C. F. and Hibbs, J. B., Role of nitric oxide synthesis in macrophage antimicrobial activity. Curr. Opin. Immunol, 3, 65-70 (1991).
7. Hwang, K.-J. and Kang, H., Design and Synthesis of furoxan derivatives as probe for the nitric oxide generation. Bull. Kor. Chem. Soc., 19, 506-507 (1998).
8. Lee, S. H., Jo, I., Lee, J. H., and Hwang, K.-J., Structural study of 3,4-bis(2-chlorophenyl) furazan A-oxide and speculation on the fragmentation. Bull. Kor. Chem. Soc., 18, 1115-1517 (1997).
9. Hwang, K.-J., Jo, I., Shin, Y. A., Yoo, S., and Lee, J. H., Furoxans as potential nitric oxide generator: Mechanistic speculation on the electron impacted fragmentation. Tetrahedron Lett., 36, 3337-3340 (1995).
10. Kim, H. J., Hwang, K.-J., and Lee, J. H, Synthesis of 4H,6H-furo[3,4-c]isoxazole derivatives as new potent fungicides and their structure activity relationship. Bull. Chem. Soc. Kor., 18, 534-540 (1997).
11. Kim, H. J., Hwang, K.-J., and Lee, J. H, Synthesis and fungicidal activities of 4iT,6A-furo[3,4-c]isoxazole derivatives as potential fungicides. Biosci. Biotech. Biochem., 58, 1191-1192 (1994).
12. Hwang, K.-J., Kim, H. J., and Lee, J. H., Fungicidal activities of 4-aryl substituted 4if,6F/-furo[3,4-c]isoxa-zole and 4i/,6iT-furo[3,4-c]isoxazoline derivatives. Korean J. Med. Chem., 4, 2-5 (1994).
13. Liu, K.-C., Shelton, B. R., and Howe, R. K., A particularly convenient preparation of benzohydroximinoyl chlorides (nitrile oxide precursors). J. Org. Chem., 45, 3916-3918 (1980).
14. Fruttero, R., Fertarotti, B., Serafino, A., Stilo, A. D., and Gasco, A., Unsymmetrically substituted furoxans. Part 11 [1]. Methylfuroxancarboaldehydes. J. Heterocyclic Chem., 26, 1345-1347 (1989).
15. Weinberg, E. D., Antifungal agents. In “Burger’s Medicinal Chemistry and Drug Discovery”, ed. Wolff, M. E., Wiley-Inter-science, New York, vol. 2, pp. 640-648 (1996).
16. Still, W. C., Kahn, M., and Mitra, A. P., Rapid chromatographic technique for preparative separations with moderate resolution. J. Org. Chem., 43, 2923-2925 (1978).