- Structural and biological evaluation of halogen derivatives of 1,9-pyrazoloanthrones towards the design of a specific potent inhibitor of c-Jun-N-terminal kinase (JNK)
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c-Jun N-terminal kinase (JNK), a member of the MAPK family, is associated with a variety of diseases and immune responses. To dissect the mechanistic role of JNKs in such processes, a specific inhibitor for JNKs holds great value. SP600125 is a widely used inhibitor of JNKs despite its non-specific activity. In an effort to obtain better specific inhibitors, three anthrapyrazolone halogenated derivatives have been synthesized and characterized. Among the three derivatives, 5-chloro-2-(2-chloroethyl)dibenzo[cd,g] indazol-6(2H)-one is clearly established as a specific inhibitor of JNK with augmented expression of chemokines in LPS-activated macrophages based on modelling studies followed by in vitro and ex vivo evaluation.
- Ganduri, Ramesh,Singh, Vikas,Biswas, Ansuman,Karothu, Durga Prasad,Sekar, Kanagaraj,Balaji, Kithiganahalli N.,Guru Row, Tayur N.
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- New Colorimetric and Fluorometric Fluoride Ion Probe Based on Anthra[1,9-cd]pyrazol-6(2H)-one
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New colorimetric and fluorometric fluoride ion probe, anthra[1,9-cd]pyrazol- 6(2H)-one (1), was synthesized by one-step condensation. The probe 1 shows F?-selective color change from colorless to pink and appearance of red fluorescence. The flu
- Hu, Yang,Liu, Yan-Yan,Li, Qiao,Sun, Jing-Yu,Hu, Sheng-Li
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- Method for producing pyrazolanthone by using 1 - aminoanthraquinone (by machine translation)
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The invention discloses a method for producing pyrazolanthone by using 1 - aminoanthraquinone, and belongs to the technical field of chemical engineering. The method comprises the following steps: (1) adding sulfuric acid in the reaction kettle, adding 65 - 70 °C aminoanthraquinone to the reaction kettle, warming up to 2 - 3h, heating the material into a reduction kettle; (1 -) adding sulfuric acid to the reaction kettle; and (2) carrying out cyclization reaction in a time-sharing stage reaction mode to obtain the pyrazolanthrapyone after the reaction is finished to 5 - 10 °C 3, adding the sodium nitrite solution to the reaction kettle after the reaction is finished 4 - 5h. The preparation method is higher in product yield and higher in purity, and can be well applied to dye production. (by machine translation)
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Paragraph 0019-0048
(2020/11/10)
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- EDC-mediated condensations of 1-chloro-5-hydrazino-9,10-anthracenedione, 1-hydrazino-9,10-anthracenedione, and the corresponding anthrapyrazoles
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The EDC-mediated condensation of 1-chloro-5-hydrazino-9,10-anthracenedione afforded an N-1 acyl anthrapyrazole instead of the expected hydrazide. The regiochemistry of the N-acyl substituent was assigned on the basis of an extensive set of NMR experiments, and identification of this isomer suggests a reaction sequence based on initial acylation and subsequent cyclization. In contrast, the parallel reaction of 1-hydrazino-9,10-anthracenedione proceeded to afford the expected hydrazide.
- Kim, MeeKyoung,Wiemer, David F.
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p. 4977 - 4980
(2007/10/03)
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- Methods for treating inflammatory conditions or inhibiting JNK
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This invention generally relates to methods for treating or preventing an inflammatory disease or disorder comprising administering to a patient in need thereof an effective amount of a Pyrazoloanthrone Derivative having the following structure: or a pharmaceutically acceptable salt thereof, wherein R1 and R2 are as defined herein.
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- Design, synthesis, and anticancer properties of 4,4′ -dihydroxybenzophenone-2,4-dinitrophenylhydrazone and analogues
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4,4′-Dihydroxybenzophenone-2,4-dinitrophenylhydrazone (A-007) has recently completed a phase I clinical trial in advanced cancer with minimal toxicity, and impressive objective responses were noted. A-007 possesses three moieties that appear to have an influence on its anticancer activities: diphenylmethane, hydrazone, and dinitrophenyl. The goals of this study were to modify A-007's chemical moieties with the ultimate goal of maximizing its anticancer activity through increased planarity and introduction of functional groups. Thirty-five phenylhydrazone analogues of A-007 were synthesized and evaluated in vitro in a human primary cancer explant assay. Anticancer activities for selected analogues were also assayed for activity vs established human/murine cell lines. One-hundred-eighty-six fresh human solid tumors were used to screen for anticancer activity. Selected analogues were assayed for therapeutic indices (vs GM-CFC from bone marrow) in preparation for preclinical studies. Several polyaryl phenylhydrazones demonstrated improved cytotoxic activities by factors of 102-103 when compared with A-007. However, the polyaryl quinone moieties of the latter analogues introduced potential toxic properties (cardiac, hematological) that do not exist with A-007.
- Morgan, Lee Roy,Thangaraj, Kanappan,LeBlanc, Blaise,Rodgers, Andrew,Wolford, Lionel T.,Hooper, Catherine L.,Fan, Dominic,Jursic, Branko S.
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p. 4552 - 4563
(2007/10/03)
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- CYCLIZATION REACTIONS OF SOME o-ACYLPHENYLHYDRAZONES
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The hydrazones Ia-Id and IIa-IId have been prepared by azo coupling of ethyl cyanacetylcarbamate and cyanacetamide, respectively, with diazotized o-aminoacetophenone, o-aminobenzophenone, 2-(2-aminobenzoyl)benzoic acid and 1-amino-9,10-antraquinone.The hydrazones Ia-Id have been alkaline or thermally cyclized to 2-aryl-4,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitriles IIIa-IIId.On boiling in strongly acidic medium the hydrazones I and II are cyclized to the corresponding 3-substituted indazoles Va-Vc and 2,6-dihydronaphthoindazol-6-one (Vd).Three hours boiling in 20percent hydrochloric acid does not affect the 1,2,4-triazine cycle of nitriles IIIa-IIId, the nitrile groups being only hydrolyzed to give the corresponding carboxylic acids IVa-IVd.On contrary, boiling in aqueous pyridine causes splitting of the 1,2,4-triazine cycle and formation of arylhydrazonocyanacetamides IIa-IId.IR and NMR spectroscopy has been used to study the possibility of simultaneous hydrogen bond to the both carbonyl groups in hydrazones I and II.
- Slouka, Jan,Bekarek, Vojtech,Lycka, Antonin
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p. 1746 - 1756
(2007/10/02)
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