Synthesis of an amantadine-based novel Schiff base and its transition metal complexes as potential ALP, α-amylase, and α-glucosidase inhibitors

Aliya Ajaz; Muhammad Ashraf Shaheen; Maqsood Ahmed; Khurram Shahzad Munawar; Abu Bakar Siddique; Abdul Karim; Nazir Ahmad; Muhammad Fayyaz Ur Rehman

doi:10.1039/d2ra07051k

Synthesis of an amantadine-based novel Schiff base and its transition metal complexes as potential ALP, α-amylase, and α-glucosidase inhibitors

RSC Adv. 2023 Jan 18;13(5):2756-2767. doi: 10.1039/d2ra07051k.

Authors

Aliya Ajaz¹, Muhammad Ashraf Shaheen¹, Maqsood Ahmed², Khurram Shahzad Munawar^{1

3}, Abu Bakar Siddique¹, Abdul Karim¹, Nazir Ahmad⁴, Muhammad Fayyaz Ur Rehman¹

Affiliations

¹ Institute of Chemistry, University of Sargodha 40100 Pakistan aliyarajput2822@gmail.com ashraf.shaheen@uos.edu.pk fayyaz9@gmail.com abubakar.siddique@uos.edu.pk abdul.karim@uos.edu.pk.
² Materials Chemistry Laboratory, Institute of Chemistry, The Islamia University of Bahawalpur Baghdad-ul-Jadeed Campus 63100 Pakistan maqsood.ahmed@iub.edu.pk.
³ Department of Chemistry, University of Mianwali Mianwali 42200 Pakistan khurramchemist@gmail.com.
⁴ Department of Chemistry, Government College University Lahore Lahore 54000 Pakistan nazirphysical@gmail.com.

Abstract

A Schiff base ligand HL, (E)-2-((adamantan-1-ylimino)methyl)-6-allylphenol, was synthesized by condensation of amantadine with 3-allyl-2-hydroxybenzaldehyde, followed by the synthesis of its Zn(ii), Co(ii), Cr(iii), and VO(iv) complexes under reflux conditions. The synthesized compounds were comprehensively elucidated by using different spectroscopic and analytical techniques: UV-Vis, ¹H and ¹³C-NMR, FT-IR, ESI-MS, thermal, and single-crystal XRD analysis. The chemical composition of the synthesized compounds was also verified by molar conductance and elemental analysis. An octahedral geometry for Cr(iii) and Co(ii) complexes, tetrahedral for Zn(ii) complex, and square pyramidal geometry have been proposed for VO(iv) complexes. The antidiabetic activities of the synthesized compounds were also evaluated by performing in vitro α-amylase and α-glucosidase inhibition studies. The Co(ii) complex exhibited the highest α-glucosidase inhibitory activity, whereas oxovanadium(iv) and zinc(ii) complexes were also found to be effective against α-amylase. In alkaline phosphatase (ALP) inhibition studies, the HL was found to be inactive, while the complexes showed remarkable enzyme inhibition in the following order: VO > Zn > Co, in a concentration-dependent manner.