Synthesis and cytotoxic activity of substituted 2-phenyl-3-hydroxy-4(1H)-quinolinones-7-carboxylic acids and their phenacyl esters

Soural, Miroslav; Hlaváč, Jan; Hradil, Pavel; Fryšová, Iveta; Hajdúch, Marián; Bertolasi, Valerio; Maloň, Michal

doi:10.1016/j.ejmech.2005.12.008

Cited by 33 publications

(36 citation statements)

References 9 publications

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“…20 Finally complexes involving these ligands are practically unknown, except for [Cu(qui) 2 ] and [Cu(tmeda)(qui)(N-baa)] complexes, where tmeda and N-baa stand for N,N,N¢,N¢-tetramethyl-ethane-1,2-diamine, and 2-(benzoylamino)benzoate, respectively.…”

Section: -16mentioning

confidence: 99%

Synthesis, characterization, DNA interaction and cleavage, and in vitro cytotoxicity of copper(ii) mixed-ligand complexes with 2-phenyl-3-hydroxy-4(1H)-quinolinone

et al. 2011

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Section: -16mentioning

confidence: 99%

Synthesis, characterization, DNA interaction and cleavage, and in vitro cytotoxicity of copper(ii) mixed-ligand complexes with 2-phenyl-3-hydroxy-4(1H)-quinolinone

et al. 2011

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“…In contrast, no one-dimensional networks are observed, while six three-dimensional and four twodimensional packing arrangements are present. Except for one (ZOBCOI; Simonov et al, 1995), all the three-dimensional crystal structures reveal the involvement of Cl atoms in N-HÁ Á ÁCl hydrogen bonds [FIWGOI (Arun Prasad et al, 2005), TCANIL02 (Gowda et al, 2007) and VABFAH (Qin et al, 2010)], weak C-HÁ Á ÁCl interactions (JEQPAX; Soural et al, 2006) or weak ClÁ Á ÁO interactions (ZOBCIC; Simonov et al, 1992). In opposition to this trend, the two-dimensional networks contain no chlorine interactions [EVICES (Liu et al, 2011), KOGSEE (Dvorkin et al, 1991) and KOGSEF (Simonov et al, 1992)], except for UNUQOK (Wang, 2011), wherein a weak C-HÁ Á ÁCl hydrogen bond is found.…”

Section: Figure 14mentioning

confidence: 99%

Cocrystals of 2,6-dichloroaniline and 2,6-dichlorophenol plus three new pseudopolymorphs of their coformers

Gerhardt

Bolte

2015

Acta Crystallogr C

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The structures of cocrystals of 2,6-dichlorophenol with 2,4-diamino-6-methyl-1,3,5-triazine, C6H4Cl2O·C4H7N5, (III), and 2,6-dichloroaniline with 2,6-diaminopyrimidin-4(3H)-one and N,N-dimethylacetamide, C6H5Cl2N·C4H6N4O·C4H9NO, (V), plus three new pseudopolymorphs of their coformers, namely 2,4-diamino-6-methyl-1,3,5-triazine-N,N-dimethylacetamide (1/1), C4H7N5·C4H9NO, (I), 2,4-diamino-6-methyl-1,3,5-triazine-N-methylpyrrolidin-2-one (1/1), C4H7N5·C5H9NO, (II), and 6-aminoisocytosine-N-methylpyrrolidin-2-one (1/1), C4H6N4O·C5H9NO, (IV), are reported. Both 2,6-dichlorophenol and 2,6-dichloroaniline are capable of forming definite synthon motifs, which usually lead to either two- or three-dimensional crystal-packing arrangements. Thus, the two isomorphous pseudopolymorphs of 2,4-diamino-6-methyl-1,3,5-triazine, i.e. (I) and (II), form a three-dimensional network, while the N-methylpyrrolidin-2-one solvate of 6-aminoisocytosine, i.e. (IV), displays two-dimensional layers. On the basis of these results, attempts to cocrystallize 2,6-dichlorophenol with 2,4-diamino-6-methyl-1,3,5-triazine, (III), and 2,6-dichloroaniline with 6-aminoisocytosine, (V), yielded two-dimensional networks, whereby in cocrystal (III) the overall structure is a consequence of the interaction between the two compounds. By comparison, cocrystal-solvate (V) is mainly built by 6-aminoisocytosine forming layers, with 2,6-dichloroaniline and the solvent molecules arranged between the layers.

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“…This confirms our previous promising experience with such substituted hydroxyquinolinones. [6] Derivative 4n exhibited even submicromolar activity except against the chemotherapy-resistant subclones CEM-DNRB and K562-Tax. [11] The cytotoxicity of the sulfonamide 6 and of the single successfully prepared sulfanylquinoline 3a has also been demonstrated.…”

Section: Biological Activitymentioning

confidence: 99%

“…General preparation of hydroxyquinolinones and aminoquinolinones. The compounds prepared according to this method were screened for their cytotoxicity by using the in vitro MTT test, and a significant activity of the hydroxyquinolinones [6][7][8] was detected, whereas 2-substituted 3-aminoquinolin-4(1H)-ones were inactive.…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis and Cytotoxic Activity of Some Symmetrical Disulfides Derived from the Quinolin‐4(1H)‐one Skeleton

et al. 2009

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The preparation of novel organic disulfides containing the 2-(substituted phenyl)quinolin-4(1H)-one ring is described. The synthesis starts from thioanthranilic acid esterified with various bromoacetophenones. Cyclization of the resulting phenacyl thioanthranilates in trifluoroacetic acid afforded a mixture of 2-(substituted phenyl)-3-sulfanylquinolin-4(1H)ones and 3,3Ј-disulfanediylbis[2-(substituted phenyl)quinolin-4(1H)-ones]. Heating of the mixture in o-xylene gave 3,3Ј-[a]

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Synthesis and cytotoxic activity of substituted 2-phenyl-3-hydroxy-4(1H)-quinolinones-7-carboxylic acids and their phenacyl esters

Cited by 33 publications

References 9 publications

Synthesis, characterization, DNA interaction and cleavage, and in vitro cytotoxicity of copper(ii) mixed-ligand complexes with 2-phenyl-3-hydroxy-4(1H)-quinolinone

Synthesis, characterization, DNA interaction and cleavage, and in vitro cytotoxicity of copper(ii) mixed-ligand complexes with 2-phenyl-3-hydroxy-4(1H)-quinolinone

Cocrystals of 2,6-dichloroaniline and 2,6-dichlorophenol plus three new pseudopolymorphs of their coformers

Efficient Synthesis and Cytotoxic Activity of Some Symmetrical Disulfides Derived from the Quinolin‐4(1H)‐one Skeleton

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