title: Synthesis, characterization, X-ray structure and biological activities of C-5-bromo-2-hydroxyphenylcalix[4]-2-methyl resorcinarene.
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.
authors.affiliation: School of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, Bangi 43600, Selangor, Malaysia. bohari@ukm.my.
authors.forename: Hamza M
authors.initials: HM
authors.lastname: Abosadiya
authors.forename: Siti Aishah
authors.initials: SA
authors.lastname: Hasbullah
authors.forename: Mukram Mohamed
authors.initials: MM
authors.lastname: Mackeen
authors.forename: Seow Chew
authors.initials: SC
authors.lastname: Low
authors.forename: Nazlina
authors.initials: N
authors.lastname: Ibrahim
authors.forename: Mamoru
authors.initials: M
authors.lastname: Koketsu
authors.forename: Bohari M
authors.initials: BM
authors.lastname: Yamin
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry; D000998:Antiviral Agents / Q000737:chemistry / Q000494:pharmacology; D047250:Calixarenes / Q000737:chemistry* / Q000494:pharmacology*; D002522:Chlorocebus aethiops; D018360:Crystallography, X-Ray; D018259:Herpesvirus 1, Human / Q000187:drug effects; D015394:Molecular Structure; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D013818:Thermogravimetry; D014709:Vero Cells
chemical_list: D000900:Anti-Bacterial Agents; D000975:Antioxidants; D000998:Antiviral Agents; C466160:resorcinarene; D047250:Calixarenes; D010649:Phenylalanine