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Molecules 2013, 18(11), 13369-13384; doi:10.3390/molecules181113369

Synthesis, Characterization, X-ray Structure and Biological Activities of C-5-Bromo-2-hydroxyphenylcalix[4]-2-methyl resorcinarene

1
School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, Bangi 43600, Selangor, Malaysia
2
Institute of Systems Biology (INBIOSIS), Universiti Kebangsaan Malaysia, Bangi 43600, Selangor, Malaysia
3
School of Biosciences and Biotechnology, Universiti Kebangsaan Malaysia, Bangi 43600, Selangor, Malaysia
4
Department of Chemistry and Biomolecular Sciences, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
*
Author to whom correspondence should be addressed.
Received: 23 September 2013 / Revised: 14 October 2013 / Accepted: 14 October 2013 / Published: 29 October 2013
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Abstract

C-5-bromo-2-hydroxyphenylcalix[4]-2-methylresorcinarene (I) was synthesized by cyclocondensation of 5-bromo-2-hydroxybenzaldehyde and 2-methylresorcinol in the presence of concentrated HCl. Compound I was characterized by infrared and nuclear magnetic resonance spectroscopic data. X-ray analysis showed that this compound crystallized in a triclinic system with space group of Pī, a = 15.9592(16)Å, b = 16.9417(17)Å, c = 17.0974(17)Å, α = 68.656(3)°, β = 85.689(3)°, γ = 81.631(3)°, Z = 2 and V = 4258.6(7)Å3. The molecule adopts a chair (C2h) conformation. The thermal properties and antioxidant activity were also investigated. It was strongly antiviral against HSV-1 and weakly antibacterial against Gram-positive bacteria. Cytotoxicity testing on Vero cells showed that it is non-toxic, with a CC50 of more than 0.4 mg/mL.
Keywords: C-5-bromo-2-hydroxyphenylcalix[4]-2-methylresorcinarene; biological activities; X-ray structural study C-5-bromo-2-hydroxyphenylcalix[4]-2-methylresorcinarene; biological activities; X-ray structural study
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Abosadiya, H.M.; Hasbullah, S.A.; Mackeen, M.M.; Low, S.C.; Ibrahim, N.; Koketsu, M.; Yamin, B.M. Synthesis, Characterization, X-ray Structure and Biological Activities of C-5-Bromo-2-hydroxyphenylcalix[4]-2-methyl resorcinarene. Molecules 2013, 18, 13369-13384.

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