Chiral γ-aryl-1H-1,2,4-triazole derivatives as highly potential antifungal agents: Design, synthesis, structure, and in vitro fungicidal activities

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 23, 2008, Pages 11367-11375

  Cao, Xiufang ^a   Li, Fei ^a   Hu, Ming ^a   Lu, Wenchang ^a   Yu, Guang Ao ^a   Sheng, Hua Liu ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

1,2,4 triazole; Antifungal activities; Chirality; Synthesis

Indexed keywords

1,2,4 TRIAZOLE; 1,2,4-TRIAZOLE; ANTIFUNGAL AGENT; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; DRUG EFFECT; FUNGUS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTIFUNGAL AGENTS; DRUG DESIGN; FUNGI; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

BOTRYTIS; COLLETOTRICHUM; COLLETOTRICHUM GOSSYPII; DOTHIORELLA GREGARIA; FUSARIUM; FUSARIUM OXYSPORUM; GIBBERELLA; GIBBERELLA ZEAE; HYPHOMYCETES; THANATEPHORUS CUCUMERIS;

EID: 58949087547     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf8026843     Document Type: Article

References (40)

1. Krämer, W.; Schirmer, U. Modern Crop Protection; Wiley-VCH: Weinheim, Germany, 2007.
2. Tanaka, K.; Tsukamoto, Y.; Sawada, Y.; Kasuya, A.; Hotta, H.; Ichinose, R.; Watanabe, T.; Toya, T.; Yokoi, S.; Kawagishi, A.; Ando, M.; Sadakane, S.; Katsumi, S.; Masui, A. Chromafenozide: A novel lepidopteran insect control agent. Annu. Rep. Sankyo Res. Lab. 2001, 53, 1-49.
3. Sheehan, D. J.; Hitchcock, C. A.; Sibley, C. M. Current and emerging azole antifungal agents. Clin. Microbiol. Rev. 1999, 12, 40-79.
4. Berg, D. Biochemical mode of action of fungicides. Ergosterol biosynthesis inhibitors. In Fungicide Chemistry: Advances and Practical Applications; Green, M. B., Spilker, D. A., Eds.; ACS Symposium Series 304; American Chemical Society: Washington, DC, 1986; pp 25-51.
5. Song, Z.; Nes, W. D. Sterol biosynthesis inhibitors: potential for transition state analogs and mechanism-based inactivators targeted at sterol methyltransferase. Lipids 2007, 42, 15-33.
6. Lombardi, P.; DiPietro, G. Heterocyclic furan compounds, their preparation and use as aromatase inhibitors. Patent Appl. WO Patent 9818791, 1998.
7. Konosu, T.; Tajima, Y.; Takeda, N.; Miyaoka, T.; Kasahara, M.; Yasuda, H.; Oida, S. Triazole antifungal. IV. Synthesis and antifungal activities of 3-acylamino-2-aryl-2-butanol derivatives. Chem. Pharm. Bull. 1991, 39, 2581-2589.
8. Bartroli, J.; Turmo, E.; Alguero, M.; Boncompte, E.; Vericat, M. L.; Conte, L.; Ramis, J.; Merlos, M.; Garcia-Rafanell, J.; Forn, J. New azole antifungals. 3. Synthesis and antifungal activity of 3-substituted-4(3H)- quinazolinones. J. Med. Chem. 1998, 41, 1869-1882.
9. Verma, A. K.; Arora, S. K.; Arora, J. S.; Rattan, A. Azole compounds as therapeutic agents for fungal infections. WO Patent 0166551, 2001.
10. Upadhayaya, R. S.; Sinha, N.; Jain, S.; Kishore, N.; Chandra, R.; Arora, S. K. Optically active antifungal azole: synthesis and antifungal activity of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl] -ethyl}-tetrazol-2-yl/1-yl)-1-[1,2,4]triazol-1-ylbutan-2-ol. Bioorg. Med. Chem. 2004, 12, 2225-2238.
11. Deas, A. H. B.; Carter, G. A.; Clark, T.; Clifford, D. R. Relationship with sensitivity to triadimefon. Pestic. Biochem. Physiol. 1986, 26, 10-21.
12. Kramer, W.; Buchel, K. H.; Draber, W. Pesticide Chemistry. Human Welfare and the Environment; Pergamon Press: London, 1983; Vol. 1, pp 223-232.
13. Im, D. S.; Cheong, C. S.; Lee, S. H.; Youn, B. H.; Kim, S. C. Chemoenzymatic synthesis of optically active 2-phenyl-2-(1H-1,2,4-triazol-1- ylmethyl)hexanenitrile. Tetrahedron 2000, 56, 1309-1314.
14. Maier, N. M.; Franco, P.; Lindner, W. Separation of enantiomers: needs, challenges, perspectives. J. Chromatogr. A 2001, 906, 3-33.
15. Toribio, L.; Nozal, M. J.; Bernal, J. L.; Jiménez, J. J.; Alonso, C. Chiral separation of some triazole pesticides by supercritical fluid chromatography. J. Chromatogr. A 2004, 1046, 249-253.
16. Kilian, M.; Atsushi, I.; Martin, N. Diamination of olefins: Synthesis, structures and reactivity of osmaimidazolidines. Chem. Eur. J. 2003, 9, 5581-5596.
17. Guile, S.; Hardern, D.; Ingall, A.; Springthorpe, B.; Willis, P. Noveltriazolo[4,5-d]pyrimidinecompounds. WO Patent 2000034283, 2000.
18. Beaudoin, S.; Gross, M. F.; Reed, A. D.; Wickenden, A. D.; Zou, A. Potassium channel inhibitors. WO Patent 2002008183, 2002.
19. Jerk, V.; Ulf, A.; Ingeborg, C.; Uli, H. Steroselectivity and generality of the palladium-catalyzed cyclopropanation of α,β-unsaturated carboxylic acids derivatized with Oppolzer's sultam. J. Chem. Soc., Perkin Trans. 1 1994, 4, 461-470.
20. Cao, X. F.; Liu, F.; Lu, W. C.; Chen, G.; Yu, G.-A.; Liu, S. H. Regio- and diastereoselective conjugate addition of Grignard reagents to aryl substituted α,β-unsaturated carbonyl compounds derived from Oppolzer's sultam. Tetrahedron 2008, 64, 5629-5636.
21. Ahlbrecht, H.; Enders, D.; Santowski, L.; Zimmermann, G. Chirale homoenolat-aquivalente, II: asymmetrische synthese 3-substituierter phenylpropionaldehyde über metallierte chirale cinnamylamine. Chem. Ber. 1989, 122, 1995-2004.
22. Shindo, M.; Koga, K.; Tomioka, K. Design, synthesis, and application of a C2 symmetric chiral ligand for enantioselective conjugate addition of organolithium to α,β-unsaturated aldimine. J. Org. Chem. 1998, 63, 9351-9357.
23. Meyers, A. I.; Shipman, M. Asymmetric Michael additions to α,β-unsaturated oxazolines. An efficient preparation of chiral α,β-disubstituted propionaldehydes. J. Org. Chem. 1991, 56, 7098-7102.
24. Tomioka, K.; Shindo, M.; Koga, K. Novel strategy of using a C2 symmetric chiral diether in the enantioselective conjugate addition of an organolithium to an α,β-unsaturated aldimine. J. Am. Chem. Soc. 1989, 111, 8266-8268.
25. Hashimoto, S.-I.; Yamada, S.-I.; Koga, K. Steroselective reactions. I. A highly efficient asymmetric synthesis of β-substituted aldehydes via 1,4-addition of Grignard reagents to optically active α,β,- unsaturated aldimines. Chem. Pharm. Bull. 1979, 27, 771-782.
26. Sabbani, S.; Hedenström, E.; Andersson, J. Lipase catalyzed acylation of primary alcohols with remotely located stereogenic centres: the resolution of (±)-4,4-dimethyl-3-phenyl-1-pentanol. Tetrahedron: Asymmetry 2007, 18, 1712-1720.
27. Soeta, T.; Kuriyama, M.; Tomioka, K. Catalytic asymmetric conjugate addition of dialkylzinc reagents to β-aryl-α,β-unsaturated N-2,4,6-triisopropylphenylsulfonylaldimines with use of N-Boc-L-Val-connected amidophosphane-copper(I) catalyst. J. Org. Chem. 2005, 70, 297-300.
28. Chang, C. J.; Fang, J. M.; Liao, L. F. Regio-, stereo-, and enantioselectivity in the electrophilic reactions of 2-amino-4-phenyl-3- butenenitriles. J. Org. Chem. 1993, 58, 1754-1761.
29. Reyes, E.; Vicario, J. L.; Carrillo, L.; Badia, D.; Uria, U.; Iza, A. (S,S)-(+)-Pseudoephedrine as chiral auxiliary in asymmetric conjugate addition and tandem conjugate addition/α-alkylation reactions. J. Org. Chem. 2006, 71, 7763-7772.
30. Pridgen, L. N.; Mokhallalati, M. K.; Wu, M. J. 1,2- vs. 1,4-Addition of nucleophilic organometallics to nonracemic 2-(1-naphthyl)-and 2-cinnamyl-1,3-oxazolidines. J. Org. Chem. 1992, 57, 1237-1241.
31. 3 centers. J. Org. Chem. 1999, 64, 3544-3553.
32. Levene, P. A.; Marker, R. E. The maximum rotations of configurationally related carboxylic acids containing a phenyl or a cyclohexyl group. J. Biol. Chem. 1935, 110, 329-342.
33. Levene, P. A.; Marker, R. E. Chemical structure and optical rotation. I. The configurational relationship of disubstituted propionic acids containing a phenyl group II. On the optically active trisubstituted methanes containing a phenyl group. J. Biol. Chem. 1931, 93, 749-774.
34. Levene, P. A.; Marker, R. E. Chemical structure and optical rotation. III. The configurational relationship of disubstituted propionic acids containing a cyclohexyl group. J. Biol. Chem. 1932, 97, 563-583.
35. Sheldrick, G. M. SHELXTL (Version 5.0); University of Göttingen: Göttingen, Germany, 2001.
36. SMART V5.628, SAINT V6.45, and SADABS; Bruker AXS Inc.: Madison, WI, 2001.
37. Clough, J. M.; Godfrey, C. R. A. The strobilurin fungicides. In Fungicidal Activity, Chemical and Biological Approaches to Plant Protection; Hutson, D. H., Miyamoto, J., Eds.; Wiley Series in Agrochemicals and Plant Protection; John Wiley & Sons: Surrey, United Kingdom, 1998; p 109.
38. Huang, W.; Zhao, P. L.; Liu, C. L.; Chen, Q.; Liu, Z. M.; Yang, G. F. Design, synthesis, and fungicidal activities of new strobilurin derivatives. J. Agric. Food Chem. 2007, 55, 3004-3010.
39. Vandewalle, M.; der Eycken, J.; Oppolzer, W.; Vullioud, C. Iridoids: Enantioselective synthesis of loganin via an asymmetric diels-alder reaction. Tetrahedron 1986, 42, 4035-4043.
40. Prashad, M.; Har, D.; Kim, H.-Y.; Repic, O. A new, economical, pratical and racemization-free method for the reductive removal of 2-oxazolidinones from N-acyloxazolidinones with sodium borohydride. Tetrahedron Lett. 1998, 39, 7067-7070.