sodium 1-amino-4-(1-anthracenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate | 1213268-79-1

• 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-(1-anthracenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate
• 英文别名: Sodium;1-amino-4-(anthracen-1-ylamino)-9,10-dioxoanthracene-2-sulfonate
• CAS: 1213268-79-1
• 化学式: C₂₈H₁₇N₂O₅S*Na
• 分子量: 516.509
• InChiKey: GURCALVPAPLZLC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-氨基蒽 、 sodium 1-amino-4-bromoanthraquinone-2-sulfonate 在 disodium hydrogenphosphate 、 sodium dihydrogenphosphate 、 铜 作用下， 以 水 为溶剂， 120.0 ℃ 、1.0 MPa 条件下， 反应 0.08h， 以10%的产率得到sodium 1-amino-4-(1-anthracenylamino)-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

• 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).