Synthesis, characterization, X-ray structure and biological activities of c-5-bromo-2-hydroxyphenylcalix[4]-2-methyl resorcinarene

Hamza M. Abosadiya, Siti Aishah Hasbullah, Muhammad Mukram Mohamed Mackeen, Seow Chew Low, Nazlina Ibrahim, Mamoru Koketsu, Bohari Mohd. Yamin

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

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 Pi, a = 15.9592(16)A, b = 16.9417(17)A, c = 17.0974(17)A, a = 68.656(3)°, β = 85.689(3)°, ? = 81.631(3)°, Z = 2 and V = 4258.6(7)A3. 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.

Original languageEnglish
Pages (from-to)13369-13384
Number of pages16
JournalMolecules
Volume18
Issue number11
DOIs
Publication statusPublished - Nov 2013

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Vero Cells
antioxidants
Human Herpesvirus 1
Gram-Positive Bacteria
activity (biology)
Bioactivity
bacteria
seats
Antiviral Agents
Magnetic Resonance Spectroscopy
Thermodynamic properties
thermodynamic properties
Antioxidants
Hot Temperature
X-Rays
X rays
nuclear magnetic resonance
X ray analysis
synthesis
Cytotoxicity

Keywords

  • Biological activities
  • C-5-bromo-2-hydroxyphenylcalix[4]-2-methylresorcinarene
  • X-ray structural study

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

Cite this

Synthesis, characterization, X-ray structure and biological activities of c-5-bromo-2-hydroxyphenylcalix[4]-2-methyl resorcinarene. / Abosadiya, Hamza M.; Hasbullah, Siti Aishah; Mohamed Mackeen, Muhammad Mukram; Low, Seow Chew; Ibrahim, Nazlina; Koketsu, Mamoru; Mohd. Yamin, Bohari.

In: Molecules, Vol. 18, No. 11, 11.2013, p. 13369-13384.

Research output: Contribution to journalArticle

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AU - Mohamed Mackeen, Muhammad Mukram

AU - Low, Seow Chew

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AU - Koketsu, Mamoru

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