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Enaminones and their molybdenum(VI) complexes as non-cytotoxic compounds with antibacterial activity (CROSBI ID 665318)

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Cvijanović, Danijela ; Damjanović, Vladimir ; Pisk, Jana ; Rubčić, Mirta ; Bilić, Luka ; Đaković, Marijana ; Hrenar, Tomica ; Lovrić, Jasna ; Vrdoljak, Višnja ; Cindrić, Marina Enaminones and their molybdenum(VI) complexes as non-cytotoxic compounds with antibacterial activity // XXV EFMC International Symposium on Medicinal Chemistry Ljubljana, Slovenija, 02.09.2018-06.09.2018

Podaci o odgovornosti

Cvijanović, Danijela ; Damjanović, Vladimir ; Pisk, Jana ; Rubčić, Mirta ; Bilić, Luka ; Đaković, Marijana ; Hrenar, Tomica ; Lovrić, Jasna ; Vrdoljak, Višnja ; Cindrić, Marina

engleski

Enaminones and their molybdenum(VI) complexes as non-cytotoxic compounds with antibacterial activity

Enaminones as a class of compounds containing conjugated N–C=C–C=O system represent a promising group of potential therapeutics showing anticonvulsant, antimicrobial, antioxidant, antitumor and cytogenetic biological activity. Due to their lipophilicity, sensitivity to minor structural changes in the N–C=C–C=O backbone and stability in solution under physiological conditions they are used as suitable starting material for the synthesis of bioactive molecules in the field of medicinal chemistry. These tridentate ONO donors also represent a significant group of ligands in the coordination chemistry of transition metals. Trying to give more insight into the correlation between chemical structure and biological activity, six non-symmetric acyclic enaminones, 4-[(2-hydroxy-5- methylphenyl)amino]pent-3-en-2-one (H2L1), 4-[(2- hydroxy-4-methylphenyl)amino]pent-3-en-2-one (H2L2), 4-[(4-hydroxy-2-methylphenyl)amino)]pent- 3-en-2-one (H2L3), 3-[(2-hydroxy-5- methylphenyl)amino]-1-phenylbut-2-en-1-one (H2L4), 3-[(2-hydroxy-4-methylphenyl)amino]-1-phenylbut-2- en-1-one (H2L5) and 3-[(4-hydroxy-2- methylphenyl)amino]-1-phenylbut-2-en-1-one (H2L6), have been synthesized and characterized (Fig. 1). The cytotoxicity of enaminones was investigated against THP-1 and HepG2 cells in vitro and corresponding IC50 values were determined by MTS assay. The antibacterial activity was tested by microdilution method against Staphylococcus aureus, Enterococcus faecalis, Escherichia coli and Moraxella catarrhalis bacterial strains to assess their MIC values. To investigate the coordination ability and influence of metal ion complexation on cytotoxicity and antibacterial activity of prepared enaminones, twelve molybdenum(VI) complexes of different nuclearity containing enaminone ligands H2L4 or H2L5 were prepared. The obtained complexes, [MoO2(L5 or 4) (MeOH)]MeOH (1MeOH and 2MeOH), [MoO2(L5 or 4) (D)] [D = pyridine, (1a and 2a), 3-methylpyridine, (1b and 2b) and 4-methylpyridine, (1c and 2c)], [{; ; ; ; ; MoO2(L5 or 4)}; ; ; ; ; 2(D)] [D = 4, 4'- bipyridine (1d and 2d)], and complexes [MoO2(L5 or 4)]n (3 and 4) were characterized and tested for cytotoxic and antibacterial activities. Enaminones and their Mo(VI) complexes were characterized by thermal analysis, IR spectroscopy and X-ray diffraction.

enaminones ; molybdenum(VI) complexes ; X-ray diffraction ; cytotoxicity ; antibacterial activity

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Podaci o skupu

XXV EFMC International Symposium on Medicinal Chemistry

poster

02.09.2018-06.09.2018

Ljubljana, Slovenija

Povezanost rada

Kemija