Über Fritzsches Reagens (β‐Dinitro‐anthrachinon)

Börnstein, E.; Schliewiensky, Herbert; Szczesny‐Heyl, Georg Victor

doi:10.1002/cber.19260591123

Cited by 7 publications

(2 citation statements)

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“…The mixture was allowed to cool to room temperature and left to stand for 48 h. The resulting precipitate was collected by filtration, washed with glacial acetic acid (3 × 30 mL) and hexane (3 × 30 mL), and dried to give a pale-yellow solid (10.34 g, 32%). Recrystallization from nitrobenzene/glacial acetic acid (1:1 v/v) afforded a pure sample of 19 : mp 290−291 °C (lit …”

Section: Methodsmentioning

confidence: 99%

“…Recrystallization from nitrobenzene/glacial acetic acid (1:1 v/v) afforded a pure sample of 19: mp 290-291 °C (lit. 38 mp 290-291 °C); NMR δ (DMSO) 8.48 (2H, dd, J ) 8.4 and 1.4 Hz, H-4,5), 8.71 (2H, dt, J ) 8.4 and 1.9 Hz, H-3,6), 8.83 (2H, t, J ) 1.9 Hz, H-1,8); MS (rel intensity) m/z 298 (100), 252 (75), 196 (22), 178 (23), 150 (67), 75 (34); calcd (M + ) 298.0226, found 298.0240. Anal.…”

Section: Methodsmentioning

confidence: 99%

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Human Telomerase Inhibition by Regioisomeric Disubstituted Amidoanthracene-9,10-diones

et al. 1998

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Telomerase is an attractive target for the design of new anticancer drugs. We have previously described a series of 1,4- and 2, 6-difunctionalized amidoanthracene-9,10-diones that inhibit human telomerase via stabilization of telomeric G-quadruplex structures. The present study details the preparation of three further, distinct series of regioisomeric difunctionalized amidoanthracene-9,10-diones substituted at the 1,5-, 1,8-, and 2,7-positions, respectively. Their in vitro cytotoxicity and Taq DNA polymerase and human telomerase inhibition properties are reported and compared with those of their 1,4- and 2,6-isomers. Potent telomerase inhibition (telIC50 values 1.3-17.3 microM) is exhibited within each isomeric series. In addition, biophysical and molecular modeling studies have been conducted to examine binding to the target G-quadruplex structure formed by the folding of telomeric DNA. These studies indicate that the isomeric diamidoanthracene-9,10-diones bind to the human telomeric G-quadruplex structure with a stoichiometry of 1:1. Plausible G-quadruplex-ligand complexes have been identified for each isomeric family, with three distinct modes of intercalative binding being proposed. The exact mode of intercalative binding is dictated by the positional placement of substituent side chains. Furthermore, in contrast to previous studies directed toward triplex DNA, it is evident that stringent control over positional attachment of substituents is not a necessity for effective telomerase inhibition.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Human Telomerase Inhibition by Regioisomeric Disubstituted Amidoanthracene-9,10-diones

et al. 1998

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Berichtigung über Methyl‐anthracene

1928

Ber. dtsch. Chem. Ges. A/B

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119-28)lv. B r a u n -B o r n s t e i n . 443Die Umsetzung niit BlC1, wurde auch hier in CS,-I,osung, erst in der Ralte, dann durch 3-stdg. Erwarmen auf dem Wasserbade, durchgefiihrt, der Schwefelkohlenstoff nach dem Zersetzen mit Eiswasser mit Wasserdampf abgeblasen, die heil3e riickstandige, von etwas Harz durchsetzte Fliissigkeit filtriert, der Kiickstand noch einmal mit heiBem Wasser ausgezogen, die Filtrate eingeengt uiid langsam erkalten gelassen : dabei krystallisierte . in einer Ausbeute, die bei Anwendung von nicht mehr als 10 g Saurechlorid 60 -6j%, bei grol3eren Mengen etwas weniger betrug, die K e t o s a u r e IV in schonen, farblosen, sofort analysenreinen Nadeln aus. 0.2114 g Sbst.: 0.5390 g CO,, 0.1015 g H,O.

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Synthesis and electrical conductivity of polymers containing trans‐1,2‐bis(9‐carbazolyl)cyclobutane units

Subramaniam

Sasakawa

Ikeda

et al. 1987

J. Polym. Sci. A Polym. Chem.

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Novel poly‐Schiff bases (PSB's) that contain trans‐1,2‐bis(9‐carbazolyl)cyclobutane(DCZB) units were synthesized by the direct polycondensation of trans‐1,2‐bis(3‐formyl‐9‐carbazolyl)cyclobutane with aromatic diamines in n‐amyl alcohol at 160°C. Complexation of these PSB's and of poly(vinyl DCZB) (PVDCZB) with iodine produced cation‐radical salts which resulted form the transfer of an electron from DCZB moieties to iodine. All the undoped polymers were insulators having electrical conductivity of the order of 10−10–10−12 S cm−1 depending on the structure of polymers. By doping with iodine, the electrical conductivity increased by several orders of magnitude and reached a value of 10−3 S cm−1 in the case of PVDCZB and 10−5–10−6 S cm−1 in the case of PSB's. The electrical conductivity of doped PSB's increased with decreasing diamine length. PVDCZB having the same iodine content per carbazole unit as poly(9‐vinyl‐carbazole) (PVK) has a greater electrical conductivity than PVK.

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Über Fritzsches Reagens (β‐Dinitro‐anthrachinon)

Cited by 7 publications

References 1 publication

Human Telomerase Inhibition by Regioisomeric Disubstituted Amidoanthracene-9,10-diones

Human Telomerase Inhibition by Regioisomeric Disubstituted Amidoanthracene-9,10-diones

Berichtigung über Methyl‐anthracene

Synthesis and electrical conductivity of polymers containing trans‐1,2‐bis(9‐carbazolyl)cyclobutane units

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