[논문]Glucopyranosylidene-spiro-benzo[b][1,4]oxazinones and -benzo[b][1,4]thiazinones: Synthesis and Investigation of Their Effects on Glycogen Phosphorylase and Plant Growth Inhibition

Kun, Sá; ndor; Ká; nya, Ná; ndor; Galó; , Norbert; Pá; hi, Andrá; s; Má; ndi, Attila; Kurtá; n, Tibor; Makleit, Pé; ter; Veres, Szilvia; Sipos, Á; dá; m; Docsa, Tibor; Somsá; k, Lá; szló

doi:10.1021/acs.jafc.9b00443

Glucopyranosylidene-spiro-benzo[b][1,4]oxazinones and -benzo[b][1,4]thiazinones: Synthesis and Investigation of Their Effects on Glycogen Phosphorylase and Plant Growth Inhibition

Journal of agricultural and food chemistry, v.67 no.24, 2019년, pp.6884 - 6891

Kun, Sándor (Department of Organic Chemistry , University of Debrecen , POB 400 , H-4002 Debrecen , Hungary) , Kánya, Nándor (Department of Organic Chemistry , University of Debrecen , POB 400 , H-4002 Debrecen , Hungary) , Galó, Norbert (Department of Organic Chemistry , University of Debrecen , POB 400 , H-4002 Debrecen , Hungary) , Páhi, András (Department of Organic Chemistry , University of Debrecen , POB 400 , H-4002 Debrecen , Hungary) , Mándi, Attila (Department of Organic Chemistry , University of Debrecen , POB 400 , H-4002 Debrecen , Hungary) , Kurtán, Tibor (Department of Organic Chemistry , University of Debrecen , POB 400 , H-4002 Debrecen , Hungary) , Makleit, Péter (Department of Agricultural Botany, Crop Physiology and Biotechnology , University of Debrecen , Bö) , Veres, Szilvia (szö) , Sipos, Ádám (rmé) , Docsa, Tibor (nyi ú) , Somsák, László (t 138 , H-4032 Debrecen , Hungary)

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Glucopyranosylidene-spiro-benzo[b][1,4]oxazinones were obtained via the corresponding 2-nitrophenyl glycosides obtained by two methods: (a) AgOTf-promoted glycosylation of 2-nitrophenol derivatives by O-perbenzoylated methyl (α-D-gluculopyranosyl bromide)heptonate or (b) Mitsunobu-type reactions of O-perbenzoylated methyl (α-D-gluculopyranose)heptonate with bulky 2-nitrophenols in the presence of diethyl azodicarboxylate (DEAD) and PPh3. Catalytic hydrogenation (H2-Pd/C) or partial reduction (e.g., H2-Pd/C, pyridine) of the 2-nitro groups led to spiro-benzo[b][1,4]oxazinones and spiro-benzo[b][1,4]-4-hydroxyoxazinones by spontaneous ring closure of the intermediate 2-aminophenyl or 2-hydroxylamino glycosides, respectively. The analogous 2-aminophenyl thioglycosides, prepared by reactions of O-perbenzoylated methyl (α-D-gluculopyranosyl bromide)heptonate with 2-aminothiophenols, were cyclized in m-xylene at reflux temperature to the corresponding spiro-benzo[b][1,4]thiazinones. O-Debenzoylation was effected by Zemplén transesterification in both series. Spiro-configurations were determined by NMR and electronic circular dichroism time-dependent density functional theory (ECD-TDDFT) methods. Inhibition assays with rabbit muscle glycogen phosphorylase b showed (1′R)-spiro{1′,5′-anhydro-D-glucitol-1′,2-benzo[b][1,4]oxazin-3(4H)-one} and (1′R)-spiro{1′,5′-anhydro-D-glucitol-1′,2-benzo[b][1,4]thiazin-3(4H)-one} to be the most efficient inhibitors (27 and 28% inhibition at 625 μM, respectively). Plant growth tests with white mustard and garden cress indicated no effect except for (1′R)-4-hydroxyspiro{1′,5′-anhydro-D-glucitol-1′,2-benzo[b][1,4]oxazin-3(4H)-one} with the latter plant to show modest inhibition of germination (95% relative to control).[FIG OMISSION]

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Glucopyranosylidene-spiro-benzo[b][1,4]oxazinones and -benzo[b][1,4]thiazinones: Synthesis and Investigation of Their Effects on Glycogen Phosphorylase and Plant Growth Inhibition

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