Chalcones: As Potent α-amylase Enzyme Inhibitors; Synthesis, In Vitro, and In Silico Studies

Title:Chalcones: As Potent α-amylase Enzyme Inhibitors; Synthesis, In Vitro, and In Silico Studies

Volume: 17 Issue: 8

Author(s): Mahboob Ali, Momin Khan*, Khair Zaman, Abdul Wadood, Maryam Iqbal, Aftab Alam, Sana Shah, Ashfaq Ur Rehman, Muhammad Yousaf, Rafaila Rafique and Khalid Mohammed Khan

Affiliation:

• Department of Chemistry, Abdul Wali Khan University, Mardan-23200,Pakistan

Keywords: Chalcones, synthesis, diabetes mellitus, α-amylase enzyme inhibition, in vitro, molecular docking.

Abstract:

Background: The inhibition of α-amylase enzyme is one of the best therapeutic approach for the management of type II diabetes mellitus. Chalcone possesses a wide range of biological activities.

Objective: In the current study chalcone derivatives (1-16) were synthesized and evaluated their inhibitory potential against α-amylase enzyme.

Methods: For that purpose, a library of substituted (E)-1-(naphthalene-2-yl)-3-phenylprop-2-en-1-ones was synthesized by Claisen-Schmidt condensation reaction of 2-acetonaphthanone and substituted aryl benzaldehyde in the presence of base and characterized via different spectroscopic techniques such as EI-MS, HRESI-MS, ¹H-, and ¹³C-NMR.

Results: Sixteen synthetic chalcones were evaluated for in vitro porcine pancreatic α-amylase inhibition. All the chalcones demonstrated good inhibitory activities in the range of IC₅₀ = 1.25 ± 1.05 to 2.40 ± 0.09 μM as compared to the standard commercial drug acarbose (IC₅₀ = 1.34 ± 0.3 μM).

Conclusion: Chalcone derivatives (1-16) were synthesized, characterized, and evaluated for their α- amylase inhibition. SAR revealed that electron donating groups in the phenyl ring have more influence on enzyme inhibition. However, to insight the participation of different substituents in the chalcones on the binding interactions with the α-amylase enzyme, in silico (computer simulation) molecular modeling analyses were carried out.

Cite this article as:

Ali Mahboob , Khan Momin *, Zaman Khair , Wadood Abdul , Iqbal Maryam , Alam Aftab , Shah Sana , Ashfaq Ur Rehman , Yousaf Muhammad , Rafique Rafaila and Khan Mohammed Khalid , Chalcones: As Potent α-amylase Enzyme Inhibitors; Synthesis, In Vitro, and In Silico Studies, Medicinal Chemistry 2021; 17 (8) . https://dx.doi.org/10.2174/1573406416666200611103039