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Article

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

by
Hamza M. Abosadiya
1,
Siti Aishah Hasbullah
1,
Mukram Mohamed Mackeen
1,2,
Seow Chew Low
3,
Nazlina Ibrahim
3,
Mamoru Koketsu
4 and
Bohari M. Yamin
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.
Molecules 2013, 18(11), 13369-13384; https://doi.org/10.3390/molecules181113369
Submission 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

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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. https://doi.org/10.3390/molecules181113369

AMA Style

Abosadiya HM, Hasbullah SA, Mackeen MM, Low SC, Ibrahim N, Koketsu M, Yamin BM. Synthesis, Characterization, X-ray Structure and Biological Activities of C-5-Bromo-2-hydroxyphenylcalix[4]-2-methyl resorcinarene. Molecules. 2013; 18(11):13369-13384. https://doi.org/10.3390/molecules181113369

Chicago/Turabian Style

Abosadiya, Hamza M., Siti Aishah Hasbullah, Mukram Mohamed Mackeen, Seow Chew Low, Nazlina Ibrahim, Mamoru Koketsu, and Bohari M. Yamin. 2013. "Synthesis, Characterization, X-ray Structure and Biological Activities of C-5-Bromo-2-hydroxyphenylcalix[4]-2-methyl resorcinarene" Molecules 18, no. 11: 13369-13384. https://doi.org/10.3390/molecules181113369

APA Style

Abosadiya, H. M., Hasbullah, S. A., Mackeen, M. M., Low, S. C., Ibrahim, N., Koketsu, M., & Yamin, B. M. (2013). Synthesis, Characterization, X-ray Structure and Biological Activities of C-5-Bromo-2-hydroxyphenylcalix[4]-2-methyl resorcinarene. Molecules, 18(11), 13369-13384. https://doi.org/10.3390/molecules181113369

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