Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche-STEBICEF, Università degli Studi di Palermo, 90128 Palermo, Italy.
Euro-Mediterranean Institute of Science and Technology (IEMEST), 90139 Palermo, Italy.
Int J Mol Sci. 2021 Nov 14;22(22):12301. doi: 10.3390/ijms222212301.
1,2,4-Oxadiazole is a heterocycle with wide reactivity and many useful applications. The reactive O-N bond is usually reduced using molecular hydrogen to obtain amidine derivatives. NHCOH-Pd/C is here demonstrated as a new system for the O-N reduction, allowing us to obtain differently substituted acylamidine, acylguanidine and diacylguanidine derivatives. The proposed system is also effective for the achievement of a reductive rearrangement of 5-(2'-aminophenyl)-1,2,4-oxadiazoles into 1-alkylquinazolin-4(1)-ones. The alkaloid glycosine was also obtained with this method. The obtained compounds were preliminarily tested for their biological activity in terms of their cytotoxicity, induced oxidative stress, α-glucosidase and DPP4 inhibition, showing potential application as anti-diabetics.
1,2,4-恶二唑是一种具有广泛反应性和许多有用应用的杂环化合物。通常使用分子氢还原反应性的 O-N 键，以获得脒衍生物。本文首次报道了 NHCOH-Pd/C 作为 O-N 还原的新体系，该体系可用于获得不同取代的酰基脒、酰基胍和二酰基胍衍生物。该体系还可有效地实现 5-(2'-氨基苯基)-1,2,4-恶二唑的还原重排，生成 1-烷基喹唑啉-4(1)-酮。该方法还获得了生物碱糖苷。初步测试了所得化合物的细胞毒性、诱导氧化应激、α-葡萄糖苷酶和 DPP4 抑制活性，显示出作为抗糖尿病药物的应用潜力。
