Organic Communications
A scientific open access journal in the field of synthetic organic chemistry and polymersLATEST ARTICLES
Synthesis of ortho-carboxamidostilbene analogues and their antidiabetic activity through in vitro and in silico approaches
Due to the recent emergence of drug-resistance of antidiabetic drugs and increase in the number of diabetes cases around the world, the search for and discovery of more effective α-amylase inhibitors is of great interest. In the present study, a new series of eighteen ortho-carboxamidostilbene derivatives were synthesized via Heck coupling reaction. The structures of the synthesized compounds were identified by various spectroscopic techniques, including HRMS, FTIR and 1D-NMR. In addition, the compounds were evaluated in vitro for their potential α-amylase inhibitory potency using acarbose as the reference drug. Compounds 5e, 5f and 6e showed remarkably moderate to good inhibitory activity with IC50 values ranging from 13.3 − 28.2 µM. These compounds showed the potent IC50 values compared to the reference drug acarbose (IC50 = 30.2 ± 0.1). The in-silico molecular docking studies revealed that the binding interactions of the most active ortho-carboxamidostilbene derivatives (5e and 6e) with binding energies of -8.7 ± 0.0 and -8.6 ± 0.2 kcal/mol. Based on the structure-activity relationship (SAR) analysis, it was established that variations in the inhibitory activities of α-amylase enzymes were attributed to distinct types of substituents at the amide group of aryl ring A, and the number and position of methoxy groups attached to aryl ring B. These findings highlight α-amylase inhibitory properties of ortho-carboxamidostilbene-containing cyclohexyl and benzyl moieties, serving as potential lead compounds in antidiabetic drug development for the treatment of type II diabetes mellitus.
DOI http://doi.org/10.25135/acg.oc.162.2401.3039 Keywords Ortho-carboxamidostilbene Heck coupling diabetes α-amylase molecular docking Available online: March 14, 2024 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.Protection of aldehydes and hydroxy compounds with acetic anhydride in presence of sulfonic acid functionalized ionic liquid
Functionalized ionic liquids (FILs) are efficient ILs for the protection of various functionalities such as aldehydes, phenol, and alcohols with acetic anhydride under neat conditions. The attracted rising interest and the subject of active research in the field of catalysis is the variety of expanded applications and yet reports on ILs are still quickly increasing. This work reports a sulfonic acid functionalized ionic liquid is an environmentally friendly, easy handling, and reusable ionic liquid catalyst for the protection of aldehydes and phenols. The catalyst was characterized with different spectroscopic techniques which indicates the fabricated IL is matching with the reported methods. The catalyst can be recycled up to eight times without substantial loss in activity. Furthermore, no chromatographic separations were needed to obtain the desired products.
DOI http://doi.org/10.25135/acg.oc.161.2312.2995 Keywords Ionic liquid acetylation room temperature short reaction time Available online: January 12, 2024 DETAILS DOWNLOAD PDF © ACG Publications. All rights reserved.