Synthesis and <i>In Vitro</i> Anti-Ulcer Effect of Triazolo-Methyl Tetrahydrobenzofuran Oxime Ether Derivatives

Abstract

The triazolo-methyl tetrahydrobenzofuran oxime ether isomers were prepared through Cu (II)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction in a high-yielding three-step reaction sequence under mild conditions. All of the intermediates and target compounds were characterized by NMR, IR, ESI-MS and elemental analysis. Thein vitroanti-ulcer activity evaluation indicated the (Z)-oxime isomer of triazolo-methyl tetrahydrobenzofuran oxime ether exhibited most potent H+/K+-ATPase inhibitory effect with the IC50˰̵̱̼͆ͅ˰̶̿˰̅˾́̅˰μ̝˾ These compounds could be potentially used as anti-ulcer agents for the treatment of acid related diseases.

Synthesis and Characterization of Triazole-Linked Bistetrahydrobenzofuran Derivatives as Anti-Ulcer Agents

“…The solvents were distilled before use following the standard procedure. (E)-2-Phenyl-6,7-dihydrobenzofuran-4(5H)-one O-prop-2-yn-1-yl oxime (I) [9], (Z)-2-phenyl-6,7-dihydrobenzofuran-4(5H)-one O-prop-2-yn-1-yl oxime (II) [9] and 4-azido-2-phenyl-4,5,6,7-tetrahydrobenzofuran (III) [7] were prepared according to the procedures described in our previous literatures.…”

Rh(iii)-catalysed C–H annulation of cis-stilbene acids with 2-diazo-1,3-diketones: facile access to 6,7-dihydrobenzofuran-4(5H)-one and α-pyrone scaffolds

“…1), which is a lactarane sesquiterpene found in mushrooms, and which has anti-fungal as well as anti-bacterial properties. 13 In addition, six-membered α-pyrone lactone species also have myriad biological activities such as antimicrobial, 14 antifungal, 15 anticancer, 16 antiulcer, 17 and immunomodulatory activities. 18 These classes of frameworks are prevalent in numerous natural products, and a few examples are shown in Fig.…”