[(4-甲氧基苯基)氨基]1-氨基-9,10-二氧代蒽-2-磺酸钠 | 78510-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: [(4-甲氧基苯基)氨基]1-氨基-9,10-二氧代蒽-2-磺酸钠
• 英文名称: sodium 1-amino-4-(2-methoxyphenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate
• 英文别名: 1-amino-4-(2-methoxyphenylamino)-2-sulfoanthraquinone sodium salt；PSB-0716；PSB-716；sodium 1-amino-4-o-methoxyanilino-9,10-dihydro-9,10-dioxoanthracene-2-sulfonate；Sodium 1-amino-4-o-methoxyanilino-9,10-dihydro-9,10-dioxoanthracene-2-sulphonate；sodium;1-amino-4-(2-methoxyanilino)-9,10-dioxoanthracene-2-sulfonate
• CAS: 78510-27-7
• 化学式: C₂₁H₁₅N₂O₆S*Na
• 分子量: 446.416
• InChiKey: REACUBXXZFBLMO-UHFFFAOYSA-M

物化性质

• 熔点：
  >300 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(4-甲氧基苯基)氨基]1-氨基-9,10-二氧代蒽-2-磺酸钠 在 盐酸 、 水 、 sodium nitrite 、 乙醇 、 锌 作用下， 反应 0.01h， 以86%的产率得到4-(2-methoxyphenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid
  参考文献：
  名称：

  Efficient and mild deamination procedure for 1-aminoanthraquinones yielding a diverse library of novel derivatives with potential biological activity

  摘要：

  A convenient in situ method is described for reductive removal of the amino group in position 1 of the anthraquinone (AQ) moiety. The reaction proceeds smoothly within a few minutes yielding novel AQ derivatives in excellent yields. Diazonium salt formation is followed by reduction with zinc in ethanol. The method has been applied to a variety of 1-amino-AQ derivatives. It allows access to a large library of new AQ derivatives which possess potential as pharmacological tools for studying purinergic signaling, and as potential drugs, for example, for the treatment of cancer and cardiovascular diseases. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.011
• 作为产物：
  描述：

  sodium 1-amino-4-bromoanthraquinone-2-sulfonate 、 邻甲氧基苯胺 在 铜 作用下， 以 aq. phosphate buffer 为溶剂， 生成 [(4-甲氧基苯基)氨基]1-氨基-9,10-二氧代蒽-2-磺酸钠
  参考文献：
  名称：

  UTP激活的P2Y 4受体有效和选择性拮抗剂的开发。

  摘要：

  P2Y 4是由尿苷5'-三磷酸（UTP）激活的Gq蛋白偶联受体，在体内，例如在肠，心脏和脑中广泛表达。到目前为止，尚未描述选择性P2Y 4受体拮抗剂。因此，我们开发和优化了基于蒽醌支架的P2Y 4受体拮抗剂。通过基于荧光的测定法评估效价，该测定法测量了稳定转染了人P2Y 4受体的1321N1星形细胞瘤细胞中UTP诱导的细胞内钙释放的抑制作用。本系列中最有效的化合物，钠1-氨基-4- [4-（2,4-二甲基苯硫基）苯基氨基] -9,10-二氧代-9,10-二氢蒽-2-磺酸盐（PSB-16133，61）表现出233 nM的IC 50值，相对于其他P2Y受体亚型具有选择性，并被认为是一种变构拮抗剂。建立了受体同源性模型，并进行了对接研究以分析配体-受体的相互作用。化合物64（PSB-1699，1-氨基-4- [4-（3-吡啶-3-基甲硫基）苯基氨基] -9,10-二氧代-9,10-二氢蒽-2-磺

  DOI：

  10.1021/acs.jmedchem.7b00030

文献信息

• Rapid and Efficient Microwave-Assisted Copper(0)-Catalyzed Ullmann Coupling Reaction:  General Access to Anilinoanthraquinone Derivatives
  作者：Younis Baqi、Christa E. Müller

  DOI：10.1021/ol070102v

  日期：2007.3.1

  reaction of bromaminic acid (1) with aniline derivatives 2a-z in phosphate buffer. Good to excellent isolated yields were obtained within only 2-20 min at 80-120 degrees C and 40-100 W. The new procedure provides the first general access to anilinoanthraquinones, furnishing a number of previously inaccessible compounds. It is superior to classical methods in all aspects, including yields, reaction time

  [结构：见文字]。苯胺蒽醌3a-z的合成是通过新的Cu（0）催化的溴酸（1）与苯胺衍生物2a-z在磷酸盐缓冲液中的微波辅助的Ullmann偶联反应完成的。在80-120摄氏度和40-100 W下仅需2-20分钟即可获得良好至优异的分离收率。新方法首次提供了苯胺基蒽醌的通用途径，从而提供了许多以前无法获得的化合物。它在所有方面都比传统方法优越，包括产率，反应时间和多功能性。
• [EN] ANTHRAQUINONE COMPOUNDS AND THEIR USES<br/>[FR] COMPOSÉS D'ANTHRAQUINONE ET LEURS UTILISATIONS
  申请人：DUNDALK INST OF TECHNOLOGY

  公开号：WO2012035122A1

  公开（公告）日：2012-03-22

  The present invention relates to a compound comprising a substituted or unsubstituted anthraquinone, or a salt or isomer thereof, for use in treating a disorder caused by or associated with dysfunctional ion channel activity. The invention finds utility in the treatment of disorders associated with smooth muscle tone and contraction, such as arterial hypertension; myocardial infarction; faecal incontinence; constipation; gastro oesophageal reflux; impaired gastrointestinal passage; urinary incontinence; erectile dysfunction; and asthma.

  本发明涉及一种包含取代或未取代蒽醌，或其盐或异构体的化合物，用于治疗由或与离子通道活性失调有关的疾病。该发明在治疗与平滑肌张力和收缩有关的疾病方面具有实用性，如动脉高血压；心肌梗死；大便失禁；便秘；胃食管反流；胃肠道通行受阻；尿失禁；勃起功能障碍；和哮喘。
• NOVEL P2Y12 RECEPTOR ANTAGONISTS
  申请人：Müller Christa E.

  公开号：US20100210654A1

  公开（公告）日：2010-08-19

  The present invention relates to novel P2Y 12 receptor antagonists useful for treating, alleviating and/or preventing diseases and disorders related to P2Y 12 receptor function as well as pharmaceutical compositions comprising such compounds and methods for preparing such compounds. The present invention is further directed to the use of these compounds, alone or in combination with other therapeutic agents, for the alleviation, prevention and/or treatment of diseases and disorders, especially the use as antithrombotic agents for inhibiting platelet aggregation.

  本发明涉及一种新的P2Y12受体拮抗剂，可用于治疗、缓解和/或预防与P2Y12受体功能相关的疾病和障碍，以及包含这些化合物的制药组合物和制备这些化合物的方法。本发明进一步涉及使用这些化合物，单独或与其他治疗剂联合使用，以缓解、预防和/或治疗疾病和障碍，特别是用作抗血栓药物来抑制血小板聚集。
• Development of Potent and Selective Inhibitors of <i>ecto</i>-5′-Nucleotidase Based on an Anthraquinone Scaffold
  作者：Younis Baqi、Sang-Yong Lee、Jamshed Iqbal、Peter Ripphausen、Anne Lehr、Anja B. Scheiff、Herbert Zimmermann、Jürgen Bajorath、Christa E. Müller

  DOI：10.1021/jm901851t

  日期：2010.3.11

  ecto-5'-Nucleotidase (eN, CD73) plays it major role in controlling extracellular adenosine levels. eN inhibitors have potential its novel drugs, for example, for the treatment of cancer. In the present study, we synthesized and investigated a series of 55 anthraquinone derivatives as potential inhibitors of eN, I I of which are novel compounds and another I I of which had previously been described but have now been synthesized by all improved method. We identified several potent inhibitors of rat eN. The most potent compounds were 1-amino-4-[4-fluoro-2-carboxyphenylamino]-9, 10-dioxo-9, 10-dihydroanthracene-2-sulfonate (45, PSB-0952, K-i = 260 nM) and 1-amino-4-[2-anthracenylamino]-9, 10-dioxo-9, 10-dihydroanthracene-2-sulfonate (52, PSB-0963, 150 nM), with 52 being the most potent eN inhibitor described to date. Selected compounds were further characterized and found to exhibit a competitive mechanism of inhibition. Investigations of ecto-nucleoside triphosphate diphosphohydrolases (NTPDases) and the P2Y receptor subtypes P2Y(2), P2Y(4), P2Y(6), and P2Y(12) showed that compound 45 exhibited the highest degree of selectivity (> 150-fold).
• Combinatorial synthesis of anilinoanthraquinone derivatives and evaluation as non-nucleotide-derived P2Y2 receptor antagonists
  作者：Stefanie Weyler、Younis Baqi、Petra Hillmann、Marko Kaulich、Andrea M. Hunder、Ingrid A. Müller、Christa E. Müller

  DOI：10.1016/j.bmcl.2007.10.082

  日期：2008.1

  A library of anilinoanthraquinone derivatives was synthesized by parallel Ullmann coupling reaction of bromaminic acid with aniline derivatives in solution using a compact parallel synthesizer. The products were purified by HPLC and evaluated as antagonists at mouse and human P2Y(2) receptors. 4-Phenylamino-substituted 1-amino-2-sulfoanthraquinones, for example, 1-amino-4-(2-methoxyphenyl)-2-sulfoanthraquinone (PSB-716), were potent P2Y(2) antagonists with IC50 values in the low micromolar range. (C) 2007 Elsevier Ltd. All rights reserved.