Sulfonamide Derivatives of 2-Amino-1-phenylethane as Suitable Cholinesterase Inhibitors
Abstract
Purpose: To evaluate the enzyme inhibition activity of N-substituted sulfamoyl derivatives of 2-amino-1- phenylethane as probable new drug candidates for the treatment of Alzheimer’s diseases.
Methods: A series of sulfamoyl derivatives, 3a-l, of 1-amino-2-phenylethane (1) were synthesized by reacting with various aryl sulfonyl chlorides, 2a-l, in the presence of aqueous Na2CO3 solution under definite pH control. All the synthesized molecules were screened against three enzymes, acetyl cholinesterase (AChE), butyryl cholinesterase (BChE) and lipoxygenase (LOX). The synthesized derivatives were further characterized by infra-red spectroscopy (IR), nuclear magnetic resonance (1HNMR) and electron ionization–mass spectrometry (EI-MS) for structure elucidation.
Results: Screening against acetyl cholinesterase (AChE), butyryl cholinesterase (BChE) and lipoxygenase (LOX) showed these molecules to be suitable inhibitors of cholinesterase enzymes, AChE and BChE, relative to eserine, the reference standard. The molecule, 3c, remained effective with 50 % inhibitory concentration (IC50) value of 82.93 ± 0.15 μM (relative to eserine with IC50 value of 0.04 ± 0.0001 μM) against AChE; similarly 3d was active against BChE with IC50 value of 45.65 ± 0.48 μM compared to eserine with IC50 value of 0.85 ± 0.00 μM. The molecule, 3f, was inactive against all the three enzymes.
Conclusion: Overall, the results indicate that these compounds are active against cholinesterase enzymes but less potent against lipoxygenase enzyme.
Keywords: 1-Amino-2-phenylethane, Aryl sulfonyl chlorides, Cholinesterase enzymes, Lipoxygenase
Submission of a manuscript to this journal is a representation that the manuscript has not been published previously and is not under consideration for publication elsewhere.
All authors named in each manuscript would be required to sign a form (to be supplied by the Editor) so that they may retain their copyright in the article but to assign to us (the Publishers) and its licensees in perpetuity, in all forms, formats and media (whether known or created in the future) to (i) publish, reproduce, distribute, display and store the contribution, (ii) translate the contribution into other languages, create adaptations, reprints, include within collections and create summaries, extracts and/or abstracts of the contribution, (iii) create any other derivative works(s) based on the contribution, (iv) to exploit all subsidiary rights in the contribution, (v) the inclusion of electronic links from the contribution to third party material where-ever it may be located, and (vi) license any thrid party to do any or all of the above.