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6,11-Dihydroxy-naphthacene-5,12-dione.

ABSTRACT: The mol-ecule of the title compound, C(18)H(10)O(4), is centrosymmetric and planar. A long phenolic O-H bond is observed [1.19 (9) Å], which is involved in an intra-molecular hydrogen bond between the phenolic and quinonoid O atoms. The mol-ecules pack in a herringbone pattern and are linked to each other via inter-molecular C-H⋯O hydrogen bonds (2.73-2.77 Å).

SUBMITTER: Tomura M

PROVIDER: S-EPMC2924183 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Unsymmetrically-Substituted 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-dione Scaffold-A Useful Tool for Bioactive Molecules Design.

Project description:Unsymmetrically N-substituted and N,N'-disubstituted 5,12-dihydrodibenzo [b,f][1,4]diazocine-6,11-diones were synthesized in the new protocol. The desired modifications of the dibenzodiazocine scaffold were introduced at the stages of proper selection of building blocks as well as post-cyclization modifications with alkylation or acylation agents, expanding the structural diversity and possible applications of synthesized molecules. The extension of developed method resulted in the synthesis of novel: tricyclic 5,10-dihydrobenzo[b]thieno[3,4-f][1,4]diazocine-4,11-dione scaffold and fused pentacyclic framework possessing two benzodiazocine rings within its structure. Additionally, the unprecedented rearrangement of 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-diones to 2-(2-aminophenyl)isoindoline-1,3-diones was observed under the basic conditions in the presence of sodium hydride for secondary dilactams. The structures of nine synthesized products have been established by single-crystal X-ray diffraction analysis. Detailed crystallographic analysis of the investigated tri- and pentacyclic systems has shed more light on their structural features. One cell line derived from non-cancerous cells (EUFA30-human fibroblasts) and three tumor cells (U87-human primary glioblastoma, HeLa-cervix adenocarcinoma, BICR18-laryngeal squamous cell carcinoma) were used to determine the cytotoxic effect of the newly synthesized compounds. Although these compounds showed a relatively weak cytotoxic effect, the framework obtained for 5,12-dihydrodibenzo[b,f][1,4]diazocine-6,11-dione could serve as a convenient privilege structure for the design and development of novel bioactive molecules suitable for drug design, development and optimization programs.

| S-EPMC7356613 | biostudies-literature

12-Benzoyl-2-methyl-naphtho-[2,3-b]indolizine-6,11-dione.

Project description:In the title compound, C(24)H(15)NO(3), the fused naphthaquin-one-pyrrole unit is approximately planar, the naphthaquinone ring system making a dihedral angle of 2.91?(10)° with the pyrrole ring. The plane of the pyrrole ring makes a dihedral angle 61.64?(14)° with that of the benzene ring of the benzoyl-methyl-ene group. The crystal structure is stablized by intra-molecular C-H?O inter-actions.

| S-EPMC3120298 | biostudies-literature

3-Acetyl-5-hy-droxy-2-methyl-anthra[1,2-b]furan-6,11-dione.

Project description:The asymmetric unit of the title compound, C(19)H(12)O(5), contains two independent mol-ecules, both slightly buckled along an axis passing through the C=O bonds of the anthraquinone ring system (r.m.s. deviation of non-H atoms = 0.082 and 0.148 Å): the benzene rings are twisted to each other by 4.3 (3)°in one mol-ecule and 10.6(3)° in the other. In both mol-ecules, the hy-droxy group forms an intra-molecular O-H⋯O hydrogen bond. The two independent mol-ecules inter-act by π-π stacking with a centroid-centroid distance of 3.539 (2) Å between hy-droxy-benzene rings of adjacent mol-ecules.

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1,4-Dihydroxy-quinoxaline-2,3(1H,4H)-dione.

Project description:The asymmetric unit of the title compound, C(8)H(6)N(2)O(4), contains one half-mol-ecule; a twofold rotation axis bisects the molecule. The quinoxaline ring is planar, which can be attributed to electron delocalization. In the crystal structure, inter-molecular O-H?O hydrogen bonds link the mol-ecules into R(2) (2)(10) motifs, leading to layers, which inter-act via phen-yl-phenyl inter-actions (C?C distances in the range 3.238-3.521?Å).

| S-EPMC2960817 | biostudies-other

2-(4-Methyl-phen-yl)-1H-anthraceno[1,2-d]imidazole-6,11-dione: a fluorescent chemosensor.

Project description:In the title compound, C(22)H(14)N(2)O(2), the five rings of the mol-ecule are not coplanar. There is a significant twist between the four fused rings, which have a slightly arched conformation, and the pendant aromatic ring, as seen in the dihedral angle of 13.16 (8)° between the anthraquinonic ring system and the pendant aromatic ring plane.

| S-EPMC2977743 | biostudies-literature

12-(4-Meth-oxy-benzo-yl)-2-methyl-benzo[f]pyrido[1,2-a]indole-6,11-dione.

Project description:In the title compound, C(25)H(17)NO(4), the indolizine fused naphthaquinone unit is approximately planar [r.m.s deviation = 0.0678 Å] and makes a dihedral angle of 57.82 (5)° with the benzene ring of the meth-oxy-benzene group. The naphtho-quinone O atoms deviate, in the same sense, from the mean plane of the fused six-membered rings by 0.2001 (14) and 0.0516 (14) Å. In the crystal there is π-π stacking of inversion-related pairs of mol-ecules [inter-planar spacing = 3.514 (2) Å].

| S-EPMC3470392 | biostudies-literature

Synthesis, molecular docking and antibacterial evaluation of new 1,4-naphthoquinone derivatives contains carbazole-6,11-dione moiety.

Project description:A new series of new 1,4-naphthoquinone derivatives containing carbazole-6,11-dione moiety, which has not been reported yet, has been synthesized from 1,4-naphthoquinone and 4-aminophenylsulfone involving a Michael addition, benzoylation, and Pd-catalyzed coupling. This set of compounds has been evaluated for in vitro antibacterial studies against different Gram-positive and Gram-negative bacteria, and most of the synthesized compounds exhibited good antibacterial activity and the minimum inhibitory concentrations (MICs) are compared with the standard drugs used. Compound 7 exhibited good antibacterial activity among all the molecules studied with the best MIC of 2.1 μg/mL against Bacillus subtilis. To understand the molecular interactions with targeted proteins, the molecular docking of all the synthesized compounds were carried out; between 14 molecules docked, compound 7 was the one with the best glide and E model score of -7.73 and -95.37, respectively. In all docked molecules, compound 5 exhibited least glide and E model score of -4.55 and -101.56, respectively. Figureᅟ

| S-EPMC4076656 | biostudies-literature

Crystal structures of two 2,3-di-ethyl-naphtho-[2,3-g]quinoxaline-6,11-dione derivatives.

Project description:Two new 5,12-disubstituted 2,3-di-ethyl-naphtho-[2,3-g]quinoxaline-6,11-dione compounds were readily synthesized from the commercial dye quinizarin. For 2,3-diethyl-5,12-di-hydroxy-naphtho-[2,3-g]quinoxaline-6,11-dione, (II), C20H16N2O4, the mol-ecule displays a near planar conformation and both hy-droxy groups participate in intra-molecular O-H?O(carbon-yl) hydrogen bonds. In the crystal, ?-? ring inter-actions [minimum ring centroid separation = 3.5493?(9)?Å] form stacks of co-planar mol-ecules down the c axis, while only minor inter-molecular C-H?O inter-actions are present. In contrast, in 2,3-diethyl-5,12-bis-(piperidin-1-yl)naphtho-[2,3-g]quinoxaline-6,11-dione, (IV), C30H34N4O2, which contains two independent, but similar, mol-ecules in the asymmetric unit, the polycyclic cores have a significant twist, with dihedral angles of 29.79?(6) and 29.31?(7)° between the terminal rings and only minor inter-molecular C-H?O hydrogen-bonding inter-actions are present. Electron density associated with additional solvent mol-ecules disordered about a fourfold axis was accounted for using the SQUEEZE procedure in PLATON [Spek (2015 ?). Acta Cryst. C71, 9-18].

| S-EPMC5598832 | biostudies-other

21-(3-Carboxy-propano-yl)-11?,17-dihydroxy-pregn-4-ene-3,20-dione monohydrate.

Project description:In the title compound, C(25)H(34)O(8)·H(2)O, the two crylohexane rings adopt chair conformations. In the crystal, the organic mol-ecule and the water mol-ecule are linked by O-H?O hydrogen bonds, generating a three-dimensional network.

| S-EPMC2979527 | biostudies-literature

5,12-Dimethyl-pyrazino-[1,2-a:4,5-a']dibenzimidazole-5,12-diium dichloride dihydrate.

Project description:The title hydrated salt, C18H18N4(2+)·2Cl(-)·2H2O, sits about an inversion centre, such that the asymmetric unit contains one half-mol-ecule. In the crystal, hydrogen bonds occur between the water mol-ecules and chloride anions, and there is π-π stacking of the benzene and imidazole rings of inversion-related pairs of mol-ecules, with a centroid-centroid distance of 3.704 (17) Å.

| S-EPMC3588989 | biostudies-literature

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