Crystal structures, in-silico study and anti-microbial potential of synthetic monocarbonyl curcuminoids

In this work the screening of 20 unsymmetrical chalcone and curcuminoids analogues in regard of their antimicrobial properties was conducted. Electron donating groups in the aromatic rings in the chalcone and curcuminoid derivatives produced higher antimicrobial effect. Compounds 1, 9 and 15 exhibited good activity against Escherichia coli and Staphylococcus aureus. These compounds were further evaluated against nine micro-organisms of pathological interest. Pharmmaper was used for target fishing of compounds against important bacterial targets. Molecular Docking helped to verify the results of these compounds against the selected bacterial target D-alanyl-D-alanine carboxypeptidase (PDB ID: 1PW1). The crystal structure of ligand and docked conformers in the active site of 1PW1 were analyzed. As a result structure-activity relationships are proposed. Structures of compounds 14 and 16 were obtained through single crystals X-ray diffraction studies. Compound 14 crystallizes in monoclinic space group P2(1)/c with unit cell dimensions a = 13.1293(3) angstrom, b = 17.5364(4) angstrom, c = 15.1433(3) angstrom, beta = 95.6440(10), V = 3469.70(13) angstrom(3) and Z = 8. Compound 16 crystallizes in triclinic space group PT with unit cell dimensions a = 6.8226(4) angstrom, b = 7.2256(4) angstrom, c = 18.1235(12) angstrom, beta = 87.322(4), V = 850.57(9) angstrom(3) and Z = 2. (C) 2017 Elsevier B.V. All rights reserved.