36681-38-6Relevant academic research and scientific papers
Crystal structures, in-silico study and anti-microbial potential of synthetic monocarbonyl curcuminoids
Ud Din, Zia,Serrano,Ademi, Kastriot,Sousa,Deflon, Victor Marcelo,Maia, Pedro Ivo da Silva,Rodrigues-Filho, Edson
, p. 529 - 534 (2017)
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 P21/c with unit cell dimensions a = 13.1293(3) ?, b = 17.5364(4) ?, c = 15.1433(3) ?, β = 95.6440(10), V = 3469.70(13) ?3 and Z = 8. Compound 16 crystallizes in triclinic space group Pī with unit cell dimensions a = 6.8226(4) ?, b = 7.2256(4) ?, c = 18.1235(12) ?, β = 87.322(4), V = 850.57(9) ?3 and Z = 2.
Phytotoxicity, structural and computational analysis of 2-methyl-1,5-diarylpentadienones
Din, Zia Ud,Rodrigues-Filho, Edson,de Cassia Pereira, Viviane,Gualtieri, Sonia Cristina Juliano,Deflon, Victor Marcelo,da Silva Maia, Pedro Ivo,Kuznetsov, Aleksey E.
, p. 239 - 247 (2017/04/26)
In our studies aimed to produce new chemicals used in weed control, 2-methyl-1,5-diarylpentadienones were synthesized by the reaction of p-methoxybenzaldehyde, p-nitrobenzaldehyde and p-N,N-dimethylbenzaldehyde, respectively, with 2-butanone, resulting in four model compounds. The phytotoxicity of these compounds against wheat coleoptiles and Sesame seedling was observed at μM concentrations, indicating good potential for their usage in weed management in the field. Spectroscopic and computational studies were performed in order to gain understanding on their mechanisms of action and to clarify some structural complexities due existence of conformers and substituent effects. These compounds probably act as hydroxyphenylpyruvate dioxygenase inhibitors. The tested compounds were characterized by spectroscopic and single crystal X-ray diffraction analyses. Solid crystalline state of the compound A (2-Methyl-1-(p-methophyphenyl)-5-(phenyl)-diarylpentadienone) is observed in the monoclinic space group P21/c with unit cell dimensions a = 14.3366(4) ?, b = 11.3788(4) ?, c = 9.6319(3) ?, β = 96.596, V = 1560.88(9) ?3 and Z = 4. Compound C (2-Methyl-1-(p-methophyphenyl)-5-(p-nitrophenyl)-diarylpentadienone) crystallizes in the monoclinic space group P21/c with unit cell dimensions a = 17.8276(9) ?, b = 7.3627(4) ?, c = 12.9740(6) ?, β = 107.6230(10), V = 1623.04(14) ?3 and Z = 4. LC-UV-MS analysis furnished important data helpful for their characterization. The spectroscopic data and computational (DFT) analysis revealed the fact that each of the compounds A-D occurs in solution as four conformers.
Unsymmetrical 1,5-diaryl-3-oxo-1,4-pentadienyls and their evaluation as antiparasitic agents
Ud Din, Zia,Fill, Taicia Pacheco,De Assis, Francisco Favaro,Lazarin-Bidóia, Danielle,Kaplum, Vanessa,Garcia, Francielle Pelegrin,Nakamura, Celso Vataru,De Oliveira, Kleber Thiago,Rodrigues-Filho, Edson
, p. 1121 - 1127 (2014/02/14)
In this work the synthesis and antiparasitical activity of new 1,5-diaryl-3-oxo-1,4-pentadienyl derivatives are described First, compounds 1a, 1b, 1c and 1d were prepared by acid-catalyzed aldol reaction between 2-butanone and benzaldehyde, anisaldehyde, p-N,N-dimethylaminobenzaldehyde and p-nitrobenzaldehyde Reacting each of the methyl ketones 1a, 1b, 1c and 1d with the p-substituted benzaldehydes under basic-catalyzed aldol reaction, we further prepared compounds 2a-2p All twenty compounds were evaluated for antiproliferative activity, particularly for promastigote of Leishmania amazonensis and epimastigote of Trypanosoma cruzi All compounds showed good activity while nitro compounds 2i and 2k showed inhibition activity at a few μM
