Design, synthesis, biologically evaluation and molecular docking of C-glycosidic oximino carbamates as novel OfHex1 inhibitors

Application of Natural Bioresources to Sustainable Agriculture: A C-Glycoside Insecticide Based on N-Acetyl-glucosamine for Regulating Insect Molting of Ostrinia furnacalis

“…The synthetic route of the first series of designed C-glycosides is illustrated in Figure 3. 34 Briefly, differently substituted carboxylic acids (1a−1d) were first reacted with Boc-protected ethylenediamine and then subjected to deprotection to yield amines 2a−2d. Next, hydroximolactone 3 was prepared in bulk (following a reported method) and was treated with 4-nitrophenyl chloroformate to Finally, deprotection of the precursors gave target compounds 6a−6d.…”

“…Figure 4 presents the synthetic route to the second series of target compounds. 21,34 We synthesized intermediates 7c, 7d and 8a−8r using previously reported synthetic routes. 17 The synthetic method for target compounds 10a−10r is consistent with the first series.…”

“…The synthetic route of the first series of designed C -glycosides is illustrated in Figure . Briefly, differently substituted carboxylic acids ( 1a – 1d ) were first reacted with Boc - protected ethylenediamine and then subjected to deprotection to yield amines 2a – 2d .…”

“…30−33 Recently, we reported a series of aromatic Cglycoside Of Hex1 inhibitors. 34 Several of these compounds exhibited more potent insecticidal activity than glucosinolates because of their inertia toward enzymatic hydrolysis. Among them, the C-glycoside compound CAUZL-A (Figure 1A) showed the highest inhibitory activity against Of Hex1 (IC 50 = 47.47 μM) and larvicidal activity against Plutella xylostella (67% at 0.05 mg/mL).…”

“…The activity of the most potent compound was almost twice that of Q1. − However, the compounds suffered from low insecticidal activity. − We speculated that the low larvicidal activity was correlated with the in vivo hydrolysis of the S -glucosinolate bonds . Converting glucosinolate bonds to carbon glycosides with higher enzymatic stability and bioavailability may be a practical solution. , The past few decades have witnessed rapid development in the facile synthetic methods for C -glycosides. − Recently, we reported a series of aromatic C -glycoside Of Hex1 inhibitors . Several of these compounds exhibited more potent insecticidal activity than glucosinolates because of their inertia toward enzymatic hydrolysis.…”