Journal article
Indole-3-acetamides: As Potential Antihyperglycemic and Antioxidant Agents; Synthesis, In Vitro α-Amylase Inhibitory Activity, Structure–Activity Relationship, and In Silico Studies

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Publication Details
Author list: Kanwal, Khalid Mohammed Khan, Sridevi Chigurupati, Farman Ali, Munissa Younus, Maha Aldubayan, Abdul Wadood, Huma Khan, Muhammad Taha, and Shahnaz Perveen
Publisher: American Chemical Society: Open Access Titles / American Chemical Society
Publication year: 2021
Journal: ACS Omega
Journal name in source: ACS Omega
Volume number: 6
Issue number: 3
Start page: 2264
End page: 2275
Number of pages: 12
ISSN: 2470-1343
Web of Science ID: 000613926400051
PubMed ID: 33521466
Scopus ID: 85099930289
eISSN: 2470-1343

Indole-3-acetamides (1–24) were synthesized via coupling of indole-3-acetic acid with various substituted anilines in the presence of coupling reagent 1,1-carbonyldiimidazole. The structures of synthetic molecules were elucidated through different spectroscopic techniques including electron ionization-mass spectroscopy (EI-MS), 1H-, 13C NMR, and high-resolution EI-MS (HREI-MS). These compounds were screened for their antihyperglycemic and antioxidant potentials. All compounds displayed good to moderate inhibition against α-amylase enzyme with IC50 values ranging between 1.09 ± 0.11 and 2.84 ± 0.1 μM compared to the standard acarbose (IC50 = 0.92 ± 0.4 μM). Compound 15 (IC50 = 1.09 ± 0.11 μM) was the most active compound of the series and exhibited good inhibition against α-amylase; in addition, this compound also exhibited good antioxidant potential with IC50 values of 0.35 ± 0.1 and 0.81 ± 0.25 μM in 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays, respectively. The binding interactions of synthetic molecules with the enzyme’s active site were confirmed via in silico studies. The current study had identified a number of lead molecules as potential antihyperglycemic and antioxidant agents.

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Last updated on 2021-20-10 at 11:21