Hamza M. Abosadiya

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

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.

1-(4-Chloro­butano­yl)-3-(3-chloro­phen­yl)thio­urea

The two independent molecules in the asymmetric unit of the title compound, C11H12Cl2N2OS, exhibit different conformations, with the benzene ring and the N2CS thiourea group forming dihedral angles of 87.40 (18) and 69.42 (15)°. An intramolecular N—H⋯O hydrogen bond is present in each molecule. Two further N—H⋯O hydrogen bonds link the independent molecules into a dimer. In the crystal, the dimers are linked by N—H⋯S and C—H⋯S hydrogen bonds, forming chains parallel to the c axis.

Synthesis, crystal structure and antioxidant evaluation of C-4-acetamidophenylcalix[4]pyrogallolarene

C-4-acetamidophenylcalix[4]pyrogallolarene was synthesized by an acid catalyzed condensation reaction of pyrogallol with 4-acetamidobenzaldehyde. The compound was characterized by IR, 1H and 13C NMR spectroscopy. Single crystal X-ray analysis revealed that the molecule crystallized in a triclinic system with space group Pī and the unit cell dimensions a= 12.2948(16) A, b= 13.4423(17) A, c= 13.5906(18) A, α =107.549(4)°, β =102.034(4)°, γ =90.535(4)°, Z= 1 and V= 2088.2(5) A3. The macrocyclic calix adopts a chair (C2h) conformation and the molecule is associated with eight DMSO molecules of crystallization. Antioxidant test by DPPH method showed that the compound exhibits good antioxidant activity of about 72%.

1-(4-Bromo­phen­yl)-3-(3-chloro­propan­oyl)thio­urea

The title compound, C10H10BrClN2OS, adopts a trans–cis conformation with respect to the position of the 3-chloropropanoyl and 4-bromophenyl groups, respectively, against the thiono C=S bond across their C—N bonds. The benzene ring makes a dihedral angle of 9.55 (16)° with the N2CS thiourea moiety. Intramolecular N—H⋯O and C—H⋯S hydrogen bonds occur. In the crystal, molecules are linked into chains along the c-axis direction by N—H⋯S, C—H⋯S and C—H⋯O hydrogen bonds.