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
ALIAS1,2, NURUL IZZATY HASSAN2,
ZAINI YUSOFF1, SHARIZAL HASAN1 & WAN YAACOB WAN AHMAD2*
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
Diserahkan: 22 Mac
2017/Diterima: 17 Ogos 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
RUJUKAN
Anand, P., Singh, B. & Singh, N. 2012.
A review on coumarins as acetylcholinesterase inhibitors for alzheimer's
disease. Bioorganic and Medicinal Chemistry 20(3): 1175–1180.
doi:10.1016/j.bmc.2011.12.042.
Banothu,
J., Vaarla, K., Bavantula, R. & Crooks, P.A. 2014. Sodium fluoride as an
efficient catalyst for the synthesis of 2,4-disubstituted-1,3-thiazoles and
selenazoles at ambient temperature. Chinese Chemical Letters 25(1):
172–175. doi:10.1016/j.cclet.2013.10.001.
Koketsu,
M. & Ishihara, H.
2008. 1,3-Selenazoles. Reference Module in Chemistry, Molecular Sciences and
Chemical Engineering Comprehensive Heterocyclic Chemistry III 4 (1):
791–821.
Kumar,
A., Gupta, M.K. & Kumar, M. 2011. An efficient non-ionic surfactant
catalyzed multicomponent synthesis of novel benzylamino coumarin derivative via
mannich type reaction in aqueous media. Tetrahedron Letters 52:
4521–4525.
Kurt,
B.Z., Gazioglu, I., Sonmez, F. & Kucukislamoglu, M. 2015. Synthesis,
antioxidant and anticholinesterase activities of novel coumarylthiazole
derivatives. Bioorganic Chemistry 59: 80–90.
doi:http://dx.doi.org/10.1016/j.bioorg.2015.02.002.
Madhav,
J.V., Kuarm, B.S. & Rajitha, B. 2008. Solid-state synthesis of
1,3-selenazoles employing cupy 2 cl 2 as a lewis acid catalyst. Synthetic
Communications 38: 3514–3522. doi:10.1080/00397910802162975.
Madhu,
C., Panguluri, N.R., Narendra, N., Panduranga, V. & Sureshbabu, V.V. 2014. One-pot synthesis
of orthogonally protected dipeptide selenazoles employing n (a) -amino
selenocarboxamides and a -bromomethyl ketones. Tetrahedron Letters 55(50): 6831−6835.
doi:http://dx.doi.org/10.1016/j.tetlet.2014.10.085.
Mahdavi,
B., Yaacob, W.A., Din, L.B., Heng, L.Y. & Ibrahim, N. 2016. Chemical
composition, antioxidant, and antibacterial activities of essential oils from Etlingera brevilabrum valeton. Records of Natural Products 10(1): 22–31.
Mao, F.,
Chen, J., Zhou, Q., Luo, Z., Huang, L. & Li, X. 2013. Novel tacrine –
ebselen hybrids with improved cholinesterase inhibitory, hydrogen peroxide and
peroxynitrite scavenging activity. Bioorganic & Medicinal Chemistry
Letters 23: 6737–6742. doi:10.1016/j.bmcl.2013.10.034.
Pizzo, C.
& Mahler, S.G. 2014. Synthesis of selenazoles by in situ cycloisomerization
of propargyl selenoamides using oxygen-selenium exchange reaction. The
Journal of Organic Chemistry 79(4): 1856–1860. doi:10.1021/jo402661b.
Ramesh,
G., Janardhan, B. & Rajitha, B. 2015. green approach: An efficient synthesis of
2,4-disubstituted-1,3-thiazoles and selenazoles in aqueous medium under
ultrasonic irradiation. Research on Chemical Intermediates 41(11):
8099–8109.
Zhao,
H-C., Shi, Y-P., Liu, Y-M., Li, C-W., Xuan, L-N., Wang, P., Zhang, K. & Chen,
B-Q. 2013. Synthesis and antitumor-evaluation of 1,3-selenazole-containing
1,3,4-thiadiazole derivatives. Bioorganic & Medicinal Chemistry Letters 23: 6577–6579.
*Pengarang untuk
surat-menyurat; email: wanyaa@ukm.edu.my