- Structural modifications of 4-aryl-4-oxo-2-aminylbutanamides and their acetyl- and butyrylcholinesterase inhibitory activity. Investigation of AChE-ligand interactions by docking calculations and molecular dynamics simulations
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Congeneric set of thirty-eight 4-aryl-4-oxo-2-(N-aryl/cycloalkyl) butanamides has been designed, synthesized and evaluated for acetyl- and butyrylcholinesterase inhibitory activity. Structural variations included cycloalkylamino group attached to C2 posit
- Vitorovi?-Todorovi?, Maja D.,Koukoulitsa, Catherine,Jurani?, Ivan O.,Mandi?, Ljuba M.,Drakuli?, Branko J.
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p. 158 - 175
(2014/06/09)
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- (E)-4-Aryl-4-oxo-2-butenoic acid amides, chalcone-aroylacrylic acid chimeras: Design, antiproliferative activity and inhibition of tubulin polymerization
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Antiproliferative activity of twenty-nine (E)-4-aryl-4-oxo-2-butenoic acid amides against three human tumor cell lines (HeLa, FemX, and K562) is reported. Compounds showed antiproliferative activity in one-digit micromolar to submicromolar concentrations.
- Vitorovic-Todorovic, Maja D.,Eric-Nikolic, Aleksandra,Kolundzija, Branka,Hamel, Ernest,Ristic, Slavica,Juranic, Ivan O.,Drakulic, Branko J.
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- Antiproliferative activity of aroylacrylic acids. Structure-activity study based on molecular interaction fields
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Antiproliferative activity of 27 phenyl-substituted 4-aryl-4-oxo-2-butenoic acids (aroylacrylic acids) toward Human cervix carcinoma (HeLa), Human chronic myelogenous leukemia (K562) and Human colon tumor (LS174) cell lines in vitro are reported. Compounds are active toward all examined cell lines. The most active compounds bear two or three branched alkyl or cycloalkyl substituents on phenyl moiety having potencies in low micromolar ranges. One of most potent derivatives arrests the cell cycle at S phase in HeLa cells. The 3D QSAR study, using molecular interaction fields (MIF) and derived alignment independent descriptors (GRIND-2), rationalize the structural characteristics correlated with potency of compounds. Covalent chemistry, most possibly involved in the mode of action of reported compounds, was quantitatively accounted using frontier molecular orbitals. Pharmacophoric pattern of most potent compounds are used as a template for virtual screening, to find similar ones in database of compounds screened against DTP-NCI 60 tumor cell lines. Potency of obtained hits is well predicted.
- Drakuli?, Branko J.,Stanojkovi?, Tatjana P.,?i?ak, ?eljko S.,Dabovi?, Milan M.
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supporting information; experimental part
p. 3265 - 3273
(2011/07/31)
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- 2-[(Carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids selectively suppressed proliferation of neoplastic human HeLa cells. A SAR/QSAR study
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A series of twenty alkyl-, halo-, and methoxy-aryl-substituted 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids were synthesized. The new compounds, called CSAB, suppressed proliferation of human cervix carcinoma, HeLa cells, in vitro in a concentration range of 0.644 to 29.48 μM/L. Two compounds exhibit antiproliferative activity in sub-micromolar concentrations (16, 19). Five compounds act in low micromolar concentrations ( 10). A strong structure-activity relationship, using estimated log P values and BCUT descriptors, was observed.
- Drakuli?, Branko J.,Jurani?, Zorica D.,Stanojkovi?, Tatjana P.,Jurani?, Ivan O.
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p. 5600 - 5603
(2007/10/03)
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