Malaysian Journal of Analytical Sciences, Vol 28 No 6 (2024): 1297 - 1307

 

EXPERIMENTAL AND SIMULATION OF HYDROXY CHALCONE DERIVATIVES AS ANTIOXIDANT AND DRUG-LIKE AGENTS

 

(Eksperimen dan Simulasi bagi Terbitan Hidroksi Kalkon sebagai Agen Antioksida dan Kesamaan Ubatan)

 

Wan Muhammad Haikal Wan Roshaimi1, Siti Nabilla Aliya Mohd Nizar1, Hifzhan Amin Azizi1, Ahmad Saifuddin Mohamad Arshad2, Juzaili Azizi2, Uwaisulqarni M. Osman3,4 and Suhana Arshad1*

 

1X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Gelugor 11800, Penang, Malaysia

2Centre for Drug Research, Universiti Sains Malaysia, Gelugor 11800, Penang, Malaysia

3Faculty of Science and Marine Environment, Universiti Malaysia Terengganu, Kuala Nerus, Terengganu 21030, Malaysia

4Advanced Nano Materials Research Group (ANOMA), Ionic State Analysis (ISA) Laboratory, Universiti Malaysia Terengganu, Kuala Nerus, Terengganu 21030, Malaysia

 

*Corresponding author: suhanaarshad@usm.my

 

Received: 30 May 2024; Accepted: 11 September 2024; Published:  29 December 2024

 

 

Abstract

Research development of antioxidant agents with drug-like properties remains a significant challenge, particularly in the limited evaluation of hydroxy chalcone derivatives. In this study, five new hydroxy chalcone derivatives were synthesized through Claisen-Schmidt condensation, achieving yields between 33% and 49%. The molecular structures of the synthesized compounds were confirmed using Infrared (IR) and Nuclear Magnetic Resonance (NMR) spectroscopy. Among the compounds, (E)-1-(4-bromophenyl)-3-(2-hydroxynaphthalen-1-yl)prop-2-en-1-one (5) exhibited superior free radical scavenging activity in the DPPH assay, while (2E,4E)-1-(anthracen-9-yl)-5-(4-hydroxy-3-methoxyphenyl)penta-2,4-dien-1-one (2) showed promising performance in the ABTS assay. SwissADME analysis predicted favourable drug-like properties for all compounds according to Lipinski's Rule, suggesting their potential as candidates for drug development.

 

Keywords: chalcone, ATR, NMR, DPPH, ABTS, SwissADME

 

Abstrak

Kajian mengenai perkembangan agen antioksida serta sifat keserupaan ubat merupakan cabaran besar terutamanya dalam penyelidikan yang terhad terhadap terbitan hidroksi kalkon. Dalam kajian ini, lima terbitan hidroksi kalkon baharu telah disintesis melalui tindak balas kondensasi Claisen-Schmidt dengan hasil antara 33% hingga 49%. Struktur molekul bagi sebatian yang disintesis telah disahkan menggunakan spektroskopi Inframerah (IR) dan Resonans Magnet Nuklear (NMR). Antara sebatian tersebut, (E)-1-(4-bromophenyl)-3-(2-hydroxynaphthalen-1-yl)prop-2-en-1-one (5) menunjukkan aktiviti penangkapan radikal bebas yang baik dalam ujian DPPH, manakala (2E,4E)-1-(anthracen-9-yl)-5-(4-hydroxy-3-methoxyphenyl)penta-2,4-dien-1-one (2) menunjukkan prestasi yang meyakinkan dalam ujian ABTS. Analisis SwissADME meramalkan sifat-sifat keserupaan ubat mengikut Peraturan Lipinski, yang menunjukkan potensi sebatian-sebatian ini sebagai calon untuk pembangunan ubat.

 

Kata kunci: kalkon, ATR, NMR, DPPH, ABTS, SwissADME

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