Synthesis of Aromatic Amino-acid Esters from 2-Phenylaminethanol and Exploring some of their Biological Activities
Date
2021-06-20
Authors
حمامرة, أسيل ماهر
Journal Title
Journal ISSN
Volume Title
Publisher
An-Najah National University
Abstract
Four compounds of aromatic amino-acid esters were prepared from the reaction of benzoic acid, and its derivatives (2-hdroxy, 3-hydroxy, 4-hydroxy benzoic acid with 2-phenyleaminethanol. The structures of these amino-acid esters were established by proton nuclear magnetic resonance (1H-NMR), Fourier transforms infrared (FT-IR), and carbon-13 (C13) nuclear magnetic resonance. The aromatic amino-acid esters were tested for their antioxidant, antibacterial, antifungal, anticancer, anti-lipase, and anti-α-glycosidase activities. The compounds' activity as antioxidants in DPPH was about (IC50 > 0.5 mg/ml), while the IC50 value of Trolox was 0.1 mg/ml. The compounds were also tested for their antibacterial and antifungal activities againstKlebsiella pneumoniae, Pseudomonas aeruginosa, Proteus vulgaris, Escherichia coli, Staphylococcus aureus, Methicillin-Resistant Staphylococcus aureus (MRSA), and Candida albicans and showed MIC value (4 mg\ml). The result didn't show significant activity toward cancer cells. Moreover, for lipase (IC50 = 231 mg/ml) and IC50 = 87.5 mg/ml for α-glycosidase inhibitory activity test, which is the same as acarbose. The synthesized aromatic compounds showed significant activities in most of the tests. The best results were in DPPH antioxidant, antimicrobial, and α-glycosidase inhibitory activities.
The synthetic compounds were prepared efficiently by the reaction of acid esters and 2-phenylaminethanol. The compound's identity was confirmed using a spectroscopic method such as 1HNmr, UV, carbon 13, and IR. The amino acid ester compounds were identified depending on some physical properties such as thin-layer chromatography and melting points. Many tests were used to confirm the compounds' biological activity for antioxidant, antibacterial, antifungal, anticancer, anti-lipase, and α-glycosidase activities. They showed significant activity in most of the tests. The best results were found in DPPH antioxidant, antimicrobial, and α-glycosidase. Overall, the results of these compounds support other researchers to complete studies for further clinical trials and make them as best choices of human drugs.