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

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

1, 1
, 1,2
, 3
, 3
, 4
 and 1,*
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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