Sains Malaysiana 47(2)(2018): 347-352

http://dx.doi.org/10.17576/jsm-2018-4702-17

Synthesis, Characterization and Antioxidant Activity of 3-(2-Amino-1,3-Selenazol-4-yl)-2H-Chromen-2-Ones Derivatives

(Sintesis, Pencirian dan Aktiviti Antioksidan Terbitan 3-(2-Amino-1,3-selenazol-4-il)-2H-Kromen-2-On)

NURUL ZAWANI ALIAS^1,2, NURUL IZZATY HASSAN², ZAINI YUSOFF¹, SHARIZAL HASAN¹ & WAN YAACOB WAN AHMAD^2*

¹Faculty of Applied Sciences, Universiti Teknologi MARA (UiTM) Perlis, 02600 Arau, Perlis Indera Kayangan, Malaysia

²School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor Darul Ehsan, Malaysia

Received: 22 March 2017/Accepted: 17 August 2017

ABSTRACT

Selenocompounds have been widely synthesized for their potential in pharmacology. Ebselen, a selenazole oxide, is a glutathione peroxidase mimic which is known to possess high antioxidant activity. Four derivatives of 3-(2-amino-1,3-selenazol-4-yl)-2H-chromen-2-ones were synthesized by reacting 3-(2-bromoacetyl)-chromen-2-one derivatives with selenourea through Hantzsch reaction using NaF as a catalyst in methanol-water (1:1) at room temperature. These reactions were completed in 30 min and purified using column chromatography eluted with n-hexane-ethyl acetate (7:3) to give 50-83% yields. All the compounds were successfully characterized using IR, ¹H and ¹³C NMR as well as mass spectrometry. The synthesized compounds were tested with DPPH assay to determine the free radical scavenging activity and were compared to gallic and ascorbic acids as standard. Nonetheless, all compounds exhibited weak free radical scavenging activity with IC₅₀ value ranging from 672.13 to 984.03 µM signifying that the derivatives may possess weak antioxidant activities.

Keywords: Coumarin; selenazole; synthesis

ABSTRAK

Sebatian seleno telah disintesis secara meluas kerana potensinya dalam bidang farmakologi. Ebselen iaitu sebatian selenazol oksida merupakan mimik glutation peroksida yang diketahui mempunyai aktiviti antipengoksida yang tinggi. Empat sebatian 3-(2-amino-1,3-selenazol-4-il)-2H-kromen-2-on disintesis dengan menindakbalaskan terbitan 3-(2-bromoasetil)-kromen-2-on dengan selenourea melalui tindak balas Hantzsch dan menggunakan NaF sebagai mangkin dalam metanol-air (1:1) pada suhu bilik. Tindak balas ini selesai dalam 30 min dan ditulenkan dengan kromatografi turus yang dielusikan dengan n-heksana-etil asetat (7:3) bagi memberikan 50-83% hasil. Kesemua sebatian dicirikan menggunakan spektroskopi IM, RMN ¹H dan ¹³C serta spektrometri jisim. Sebatian yang telah disintesis diuji dengan asai DFPH bagi menentukan aktiviti penggarutan radikal bebas dan dibandingkan dengan asid galik dan askorbik sebagai piawai. Walau bagaimanapun, kesemua sebatian menunjukkan aktiviti penggarutan radikal bebas yang lemah dengan julat nilai IC₅₀ diantara 672.13 ke 984.03 µM menandakan terbitan sebatian ini mungkin mempunyai aktiviti antioksida yang lemah.

Kata kunci: Koumarin; selenazol; sintesis

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*Corresponding author; email: wanyaa@ukm.edu.my