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Synthesis, Fungicidal Activity, and Sterol 14α-Demethylase Binding Interaction of 2‑Azolyl-3,4-dihydroquinazolines on Penicillium digitatum

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journal contribution
posted on 19.02.2016, 22:06 by Wen-Jin Li, Qian Li, De-Li Liu, Ming-Wu Ding
A series of new 2-azolyl-3,4-dihydroquinazolines 6 was synthesized by direct cyclization of imidazole or 1,2,4-triazole with carbodiimides 4, which were obtained from aza-Wittig reaction of iminophosphorane 3 with isocyanate. The preliminary bioassay results demonstrated that most of the 2-imidazolyl-3,4-dihydroquinazolines 6a6i exhibited good to significant fungicidal activity against Penicillium digitatum, whereas 2-triazolyl-3,4-dihydroquinazolines 6j6t exhibited low fungicidal activity. Some of the 2-imidazolyl-3,4-dihydroquinazolines 6a6i also exhibited strong binding interaction with the cytochrome P450-dependent sterol 14α-demethylase (CYP51). For example, compound 6e showed the best fungicidal activity against P. digitatum with IC50 = 4.14 μg/mL and the best CYP51 binding activity with Kd = 0.34 μg/mL, both superior to those of the agricultural fungicide triadimefon.