Upon treatment with hydroxylamine‐, benzyl‐ and benzoyl‐protected β‐D‐glucopyranosyl cyanides efficiently afforded the corresponding amidoximes. They reacted by O‐acylation in the presence of carboxylic acids or acyl chlorides to provide benzyl‐ and benzoyl‐protected O‐acylamidoximes. The latter were isolated and fully characterized. Thermal cyclization of O‐acylamidoximes yielded the corresponding 5‐substituted 3‐C‐β‐D‐glucopyranosyl‐1,2,4‐oxadiazoles, either in a “one‐pot” procedure (benzylated series), or in two steps (benzoylated series). The twelve 5‐substituted 1,2,4‐oxadiazoles obtained upon debenzoylation were assayed against glycogen phosphorylase (GP). 3‐C‐(β‐D‐Glucopyranosyl)‐5‐(2‐naphthyl)‐1,2,4‐oxadiazole was the best inhibitor of rabbit muscle glycogen phosphorylase b (Ki = 38.4 ±3.0 μM). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Photoluminescent materials, that are now ubiquitous in our everyday life, have particularly attracted the attention of the scientific community these past few years due to potential important applications such as in bioimaging, sensing, or optoelectronics. In this context, relatively few different families of molecules have been reported to exhibit fluorescence in the aggregated or solid-state through the excited-state intramolecular proton transfer (ESIPT) photochemical process. The preparation and subsequent determination of photochemical properties of an underexplored family of 1,5-benzodiazepin-2-one derivatives are reported. From these data and X-ray diffraction analysis study, it emerged that photoluminescence (in the range 520-655 nm) was mostly attributed to ESIPT. The photoluminescent potential of 1,5-benzodiazepin-2-ones, their facile access, and functionalization were demonstrated through the preparation of two fluorogenic probes for the selective detection of biothiols.

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