1-acetyl-5-hydroxyanthracene-9,10-dione | 63972-38-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-acetyl-5-hydroxyanthracene-9,10-dione
• 英文别名: 1-Hydroxy-5-acetylanthrachinon；1-Hydroxy-5-acetyl-9,10-anthrachinon；1-Acetyl-5-hydroxy-anthraquinone
• CAS: 63972-38-3
• 化学式: C₁₆H₁₀O₄
• 分子量: 266.253
• InChiKey: RROLKYCVTJGMND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-acetyl-5-hydroxyanthracene-9,10-dione 、 1-碘代丙烷 在 silver(l) oxide 作用下， 生成 1-Acetyl-5-propoxyanthracene-9,10-dione
  参考文献：
  名称：

  Antiproliferative activities and SAR studies of substituted anthraquinones and 1,4-naphthoquinones

  摘要：

  STAT3 is constitutively active in a large variety of cancers. The search for STAT3 inhibitors led to the discoveries of LLLs 3 and 12, which are substituted anthraquinones. LLL12 is an extremely potent compound that exhibits high levels of antiproliferative activity. Herein the synthesis and evaluation of compounds containing either an anthraquinone or 1,4-naphthoquinone moiety are reported. Analogs were evaluated in several cancer cell lines. Interestingly, it was found that the anthraquinones did not follow the same trends as the 1,4-naphthoquinones in regards to potency. LLL12, which contains a sulfonamide at position 1, was found to be the most potent of the anthraquinones. In contrast, the methyl ketone and methyl ester derivatives (LLLs 3.1 and 5.1) were found to be the most potent of the 1, 4-naphthoquinones. Selected 1,4-naphthoquinones were also evaluated in the STAT3 fluorescence polarization assay in order to evaluate their abilities to bind to the STAT3 SH2 domain. They were found to have similar affinities, and their activities suggest that STAT3 is one of their molecular targets. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.098
• 作为产物：
  描述：

  蒽绛酚 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 1,3-双(二苯基膦)丙烷 、 水 、 palladium diacetate 、 potassium carbonate 、 苯甲醚 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 1-acetyl-5-hydroxyanthracene-9,10-dione
  参考文献：
  名称：

  US2014/275263

  摘要：

  公开号：

文献信息

• Naphto- and anthraquinones of Streptomyces thermoviolaceusWR-141. Structures and model syntheses
  作者：J.St. Pyrek、O. Achmatowicz、A. Zamojski

  DOI：10.1016/0040-4020(77)80309-8

  日期：1977.1

  In addition to previously identified antibiotic granaticin 1 Streptomyces thermoviotaceus WR-141 was shown to produce dihydrogranaticin 2, and anthraquinone pigments 5, and 6. Model synthesis of the chromophore and dihydropyran part of these antibiotic pigments are described.

  除了先前确定的抗生素Granaticin 1外，热链霉菌WR-141还显示产生二氢Granaticin 2和蒽醌色素5和6。描述了这些抗生素颜料的生色团和二氢吡喃部分的模型合成。
• Design, synthesis, and studies of small molecule STAT3 inhibitors
  作者：Deepak Bhasin、Katryna Cisek、Trupti Pandharkar、Nicholas Regan、Chenglong Li、Bulbul Pandit、Jiayuh Lin、Pui-Kai Li

  DOI：10.1016/j.bmcl.2007.10.031

  日期：2008.1

  A series of small molecule STAT3 inhibitors originally derived from our lead compound STA 21 were synthesized and evaluated. The most potent compound in this series, compound 1, exhibited the same anti-proliferative activities as STA 21 against prostate cancer cell lines that express constitutively active STAT3. Molecular docking showed compound 1 bound to the STAT3 beta SH2 domain in a similar manner as STA 21. (C) 2007 Elsevier Ltd. All rights reserved.
• MICROEMULSION TOPICAL DELIVERY PLATFORM
  申请人：Eyecro, LLC

  公开号：EP2968139B1

  公开（公告）日：2018-05-23
• STAT3 INHIBITING COMPOSITIONS AND METHODS
  申请人：Farjo Rafal A.

  公开号：US20110077306A1

  公开（公告）日：2011-03-31

  STA-21-related compounds, for example CLT-005, are shown to prevent dimerization of STAT3, thereby inhibiting STAT3 activity. Inhibition of STAT3 activity is shown to reduce intraocular inflammation and neovascularization, symptoms of eye-related diseases such as age-related macular degeneration. Inhibition of STAT3 prevents STAT3 from transcriptionally activating downstream gene targets that are known to be associated with retinal inflammation and neovascularization and such disorders as age-related macular degeneration.
• 1-ACETYL-5-HYDROXYANTHRACENE-9,10-DIONE FOR TREATMENT OF RETINAL DISEASE
  申请人：Farjo Rafal A.

  公开号：US20120059067A1

  公开（公告）日：2012-03-08

  A composition may include a pharmaceutical carrier and an amount, therapeutically effective for the treatment of a retinal disease, of CLT-005 (1-acetyl-5-hydroxyanthracene-9,10-dione), wherein the retinal disease is characterized by at least one of inflammation, angiogenesis, or neovascularization, and wherein the composition is prepared for administration topically. The composition may be administered topically to a subject's eye.