sodium 1-amino-4-(4-anilinophenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate | 1007600-12-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: sodium 1-amino-4-(4-anilinophenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate
• 英文别名: Sodium;1-amino-4-(4-anilinoanilino)-9,10-dioxoanthracene-2-sulfonate
• CAS: 1007600-12-5
• 化学式: C₂₆H₁₈N₃O₅S*Na
• 分子量: 507.502
• InChiKey: PQCMELOIIPXKML-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  sodium 1-amino-4-bromoanthraquinone-2-sulfonate 、 对氨基二苯胺 在 disodium hydrogenphosphate 、 sodium dihydrogenphosphate 、 铜 作用下， 以 水 为溶剂， 生成 sodium 1-amino-4-(4-anilinophenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate
  参考文献：
  名称：

  Development of Potent and Selective Inhibitors of ecto-5′-Nucleotidase Based on an Anthraquinone Scaffold

  摘要：

  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).

  DOI：

  10.1021/jm901851t

文献信息

• High-Affinity, Non-Nucleotide-Derived Competitive Antagonists of Platelet P2Y₁₂ Receptors
  作者：Younis Baqi、Kerstin Atzler、Meryem Köse、Markus Glänzel、Christa E. Müller

  DOI：10.1021/jm9003297

  日期：2009.6.25

  Anthraquinone derivatives related to the moderately potent, nonselective P2Y(12) receptor antagonist reactive blue 2 (6) have been synthesized and optimized with respect to P2Y(12) receptor affinity. A radioligand binding assay utilizing human blood platelet membranes and the P2Y(12) receptor-selective antagonist radioligand [H-3]2-propylthioadenosine-5'-adenylic acid (1,1-dichloro-1-phosphonomethyl-1-phosphonyl) anhydride ([H-3]PSB-0413) was applied for compound testing. 1-Amino-2-sulfoanthraquinone derivatives bearing a (p-phenylamino)anilino substitution in the 4-position and an additional acidic function in the meta-position of the aniline ring showed high P2Y(12) receptor affinity. These new anthraquinone derivatives became accessible by a recently developed copper(0)-catalyzed Ullmann coupling reaction of 1-amino-4-bromoanthraquinone derivatives with anilines in phosphate buffer under microwave irradiation. The most potent compounds exhibited K-i values of 24.9 nM (1-amino-4-[4-phenylamino-3-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate, PSB-0739, 39), and 2 1.0 nM (1-amino-4-[4-phenylamino-3-carboxyphenylamino]- 9,10-dioxo-9,10-dihydroanthracene-2-sulfonate, PSB-0702, 41), respectively. 1-Amino-2-sulfo-4-anilinoanthraquinone derivatives appeared to be noncytotoxic, as shown for selected derivatives at two human cell lines (melanoma and astrocytoma). Compounds 39 and 41 represent new lead structures for the development of antithrombotic drugs.
• 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.
• 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).