Synthesis, fungicidal activity, and sterol 14α-demethylase binding interaction of 2-azolyl-3,4-dihydroquinazolines on Penicillium digitatum

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 7, 2013, Pages 1419-1426

  Li, Wen Jin ^a   Li, Qian ^a   Liu, De Li ^a   Ding, Ming Wu ^a  

^a CENTRAL CHINA NORMAL UNIVERSITY   (China)

Author keywords

14 demethylase; aza Wittig reaction; binding constant; fungicidal activity; imidazole; quinazoline; triazole

Indexed keywords

AZA-WITTIG REACTION; BINDING CONSTANT; DEMETHYLASE; FUNGICIDAL ACTIVITY; IMIDAZOLE; QUINAZOLINES; TRIAZOLE;

ALCOHOLS; BINDING ENERGY; BIOASSAY; CHEMICAL REACTIONS; NITROGEN COMPOUNDS;

HYDROPHOBICITY;

1,2,4 TRIAZOLE; 1,2,4-TRIAZOLE; CYTOCHROME P450; FUNGICIDE; IMIDAZOLE; IMIDAZOLE DERIVATIVE; QUINAZOLINE DERIVATIVE; STEROL 14ALPHA DEMETHYLASE; TRIADIMEFON; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; DRUG EFFECT; ENZYMOLOGY; METABOLISM; PENICILLIUM; PROTEIN BINDING; SYNTHESIS;

CYTOCHROME P-450 ENZYME SYSTEM; FUNGICIDES, INDUSTRIAL; IMIDAZOLES; PENICILLIUM; PROTEIN BINDING; QUINAZOLINES; STEROL 14-DEMETHYLASE; TRIAZOLES;

EID: 84874102450     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf305355u     Document Type: Article

References (33)

1. Palou, L.; Smilanick, J. L.; Usall, J.; Vigríäs, I. Control of postharvest blue and green molds of oranges by hot water, sodium carbonate and sodium bicarbonate Plant Dis. 2001, 85, 371-376
2. Droby, S.; Eick, A.; Macarisin, D.; Cohen, L.; Rafael, G.; Stange, R.; McColum, G.; Dudai, N.; Nasser, A.; Wisniewski, M.; Shapira, R. Role of citrus volatiles in host recognition, germination and growth of Penicillium digitatum and Penicillium italicum Postharvest Biol. Technol. 2008, 49, 386-396
3. Sheehan, D. J.; Hitchcock, C. A.; Sibley, C. M. Current and emerging azole antifungal agents Clin. Microbiol. Rev. 1999, 12, 40-79
4. Tsuda, M.; Itoh, H.; Kato, S. Evaluation of the systemic activity of simeconazole in comparison with that of other DMI fungicides Pest Manag. Sci. 2004, 60, 875-880
5. Lepesheva, G. I.; Waterman, M. R. Sterol 14α-demethylase cytochrome P450 (CYP51), a P450 in all biological kingdoms Biochim. Biophys. Acta 2007, 1770, 467-477
6. Popkov, S. V.; Kovalenko, L. V.; Bobylev, M. M.; Molchanov, O. Y.; Krimer, M. Z.; Tashchi, V. P.; Putsykin, Y. G. The synthesis and fungicidal activity of 2-substituted 1-azol-1-ylmethyl-6-arylidenecyclohexanols Pestic. Sci. 1997, 49, 125-129
7. Song, H.; Liu, Y.; Xiong, L.; Li, Y.; Yang, N.; Wang, Q. Design, synthesis, and insecticidal activity of novel pyrazole derivatives containing α-hydroxymethyl- N -benzyl carboxamide, α-chloromethyl- N -benzyl carboxamide and 4,5-dihydrooxazole moieties J. Agric. Food Chem. 2012, 60, 1470-1479
8. Sun, R.; Li, Y.; Xiong, L.; Liu, Y.; Wang, Q. Design, synthesis and insecticidal evaluation of new benzoylureas containing isoxazoline and isoxazole group J. Agric. Food Chem. 2011, 59, 4851-4859
9. Wang, H.; Yang, Z.; Fan, Z.; Wu, Q.; Zhang, Y.; Mi, N.; Wang, S.; Zhang, Z.; Song, H.; Liu, F. Synthesis and insecticidal activity of N-tert -butyl- N, N ′-diacylhydrazines containing 1,2,3-thiadiazoles J. Agric. Food Chem. 2011, 59, 628-634
10. Cui, Z.-N.; Shi, Y.-X.; Zhang, L.; Ling, Y.; Li, B.-J.; Nishida, Y.; Yang, X.-L. Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4- oxadiazole derivatives J. Agric. Food Chem. 2012, 60, 11649-11656
11. Singh, P. K. Synthesis and fungicidal activity of novel 3-(substituted/unsubstituted phenylselenonyl)-1-ribosyl/deoxyribosyl-1 H -1,2,4-triazole J. Agric. Food Chem. 2012, 60, 5813-5818
12. Zhao, L.; Liu, D.; Zhang, Q.; Zhang, S.; Wan, J.; Xiao, W. Expressionand homology modeling of sterol 14α-demethylase from Penicillium digitatum FEMS Microbiol. Lett. 2007, 277, 37-43
13. Zhang, J. H.; Zhao, L.; Zhang, J.; Han, R.; Li, S. X.; Yuan, Y. Z.; Wan, J.; Xiao, W. J.; Liu, D. L. Optimised expression and spectral analysis of the target enzyme CYP51 from Penicillium digitatum with possible new DMI fungicides Pest Manag. Sci. 2010, 66, 1344-1350
14. Cao, X. F.; Hu, M.; Zhang, J.; Li, F.; Yang, Y. H.; Liu, D. L.; Liu, S. H. Determination of stereoselective interaction between enantiomers of chiral γ-aryl-1 H -1,2,4-triazole derivatives and Penicillium digitatum J. Agric. Food Chem. 2009, 57, 6914-6919
15. Ming, Z. H.; Xu, S. Z.; Zhou, L.; Ding, M. W.; Yang, J. Y.; Yang, S.; Xiao, W. J. Organocatalytic synthesis and sterol 14α-demethylase binding interactions of enantioriched 3-(1 H -1,2,4-triazol-1-yl)butyl benzoates Bioorg. Med. Chem. Lett. 2009, 19, 3938-3940
16. Saito, T.; Ohmori, H.; Furuno, E.; Motoki, S. Conjugated heterocumulenes. Synthesis of conjugated carbodiimides and their facile conversion via intramolecular cycloaddition into nitrogen heterocycles, quinoline and pyrido[2,3- b ]indole (α-carboline) derivatives J. Chem. Soc., Chem. Commun. 1992, 22
17. Saito, T.; Tsuda, K.; Saito, Y. A facile and efficient carbodiimide-mediated synthesis of dihydroquinazolines via a tandem nucleophilic addition-intramolecular hetero conjugate addition annulation strategy Tetrahedron Lett. 1996, 37, 209-212
18. Cao, X. F.; Li, F.; Hu, M.; Lu, W. C.; Yu, G.-A.; Liu, S. H. Chiral γ-aryl-1 H -1,2,4-triazole derivatives as highly potential antifungal agents: design, synthesis, structure and in vitro fungicidal activities J. Agric. Food Chem. 2008, 56, 11367-11375
19. 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; Wiley: Surrey, UK, 1998; p 109.
20. Franken, K. L.; Hiemstra, H. S.; Meijgaarden, K. E.; Subronto, Y.; Hartigh, J.; Ottenhoff, T. H.; Drijfhout, J. W. Purification of His-tagged proteins by immobilized chelate affinity chromatography: the benefits from the use of organic solvent Protein Express. Purif. 2000, 18, 95-99
21. Duff, S. M. G.; Davila-Aponte, J.; Thompson, R. The development of a medium throughput assay for lanosterol synthase from Leptosphaeria nodorum: vomparison of the enzyme from L. nodorum, Saccharomyces cerevisiae, and two species of Fusarium Pestic. Biochem. Physiol. 2005, 83, 97-106
22. Braford, M. M.; Mcrorie, R. A.; Williams, W. L. A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding Anal. Biochem. 1976, 72, 248-254
23. Guardiola-Diaz, H. M.; Foster, L.-A.; Mushrush, D.; Vaz, A. D. N. Azole-antifungal binding to a novel cytochrome P450 from Myobacterium tuberculosis: implications for treatment of tuberculosis Biochem. Pharmacol. 2001, 61, 1463-1470
24. Omura, T.; Sato, R. The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature J. Biol. Chem. 1964, 239, 2370-2378
25. Segel, I. H. Enzyme Kinetics Behaviour and Analysis of Rapid Equilibrium and Steady-State Enzyme Systems; Wiley: New York, 1975.
26. Bentley, T. W.; Jones, R. V. H.; Wareham, P. J. A general anionic mechanism for thermodynamic control of regioselectivity in N-alkylation and acylation of heterocycles Tetrahedron Lett. 1989, 30, 4013-4016
27. Smith, K.; Small, A.; Hutchings, M. G. Regiospecific synthesis of α-alkoxy and α-alkylthio-1-alkyl-1,2,4-triazoles from aldehydes Synlett 1991, 485-486
28. Smith, K.; Hammond, M. E. W.; James, D. M.; Ellison, I. J.; Hutchings, M. G. Regiospecific synthesis of 1-substituted 1,2,4-triazoles by reaction of 1,2,4-triazole with aldehydes Chem. Lett. 1990, 351-354
29. Ding, M. W.; Zeng, G. P.; Liu, Z. J. A regiospecific synthesis of 1-heterocyclic substituted 1,2,4-triazoles via addition reaction of 1,2,4-triazole with functionalized carbodiimide Synth. Commun. 2002, 32, 3057-3062
30. Palacios, F.; Alonso, C.; Aparicio, D.; Rubiales, G.; Santos, J. M. The aza-Wittig reaction: an efficient tool for the construction of carbon-nitrogen double bonds Tetrahedron 2007, 63, 523-575
31. Liu, Y.; Liu, J.; Qi, X.; Du, Y. One-pot synthesis of 2,4-disubstituted thiazoline from β-azido disulfide and carboxylic acid J. Org. Chem. 2012, 77, 7108-7113
32. Naganaboina, V. K.; Chandra, K. L.; Desper, J.; Rayat, S. An easy entry into 2-halo-3-aryl-4(3 H)-quinazoliniminium halides from heteroenyne-allenes Org. Lett. 2011, 13, 3718-3721
33. Wang, H. Q.; Zhou, W. P.; Wang, Y. Y.; Lin, C. R. Synthesis and antifungal activities of novel 5-amino-6-arylamino-1 H -pyrazolo[3,4- d ]pyrimidin-4(5 H)-one derivatives J. Agric. Food Chem. 2008, 56, 7321-7325