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


ABSTRACT: 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.

SUBMITTER: Kanwal 

PROVIDER: S-EPMC7841949 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

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Indole-3-acetamides: As Potential Antihyperglycemic and Antioxidant Agents; Synthesis, <i>In Vitro</i> α-Amylase Inhibitory Activity, Structure-Activity Relationship, and <i>In Silico</i> Studies.

Kanwal   Khan Khalid Mohammed KM   Chigurupati Sridevi S   Ali Farman F   Younus Munissa M   Aldubayan Maha M   Wadood Abdul A   Khan Huma H   Taha Muhammad M   Perveen Shahnaz S  

ACS omega 20210112 3


Indole-3-acetamides (<b>1-24</b>) 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), <sup>1</sup>H-, <sup>13</sup>C NMR, and high-resolution EI-MS (HREI-MS). These compounds were screened for their antihyperglycemic and antioxidant potentials. All  ...[more]

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