sodium 1-amino-9,10-dioxo-4-(propylamino)-9,10-dihydroanthracene-2-sulfonate | 34824-61-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: sodium 1-amino-9,10-dioxo-4-(propylamino)-9,10-dihydroanthracene-2-sulfonate
• 英文别名: Sodium;1-amino-9,10-dioxo-4-(propylamino)anthracene-2-sulfonate；sodium;1-amino-9,10-dioxo-4-(propylamino)anthracene-2-sulfonate
• CAS: 34824-61-8
• 化学式: C₁₇H₁₅N₂O₅S*Na
• 分子量: 382.372
• InChiKey: KRKNWWBEHYOJHQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.23
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  sodium 1-amino-9,10-dioxo-4-(propylamino)-9,10-dihydroanthracene-2-sulfonate 在 盐酸 、 水 、 sodium nitrite 、 乙醇 、 锌 作用下， 反应 0.01h， 以96%的产率得到4-propylamino-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：

  正丙胺 、 sodium 1-amino-4-bromoanthraquinone-2-sulfonate 在 铜 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.4h， 以57%的产率得到sodium 1-amino-9,10-dioxo-4-(propylamino)-9,10-dihydroanthracene-2-sulfonate
  参考文献：
  名称：

  肺炎军团菌细菌外切核苷酸酶Lp1NTPDase的抑制剂。

  摘要：

  嗜肺军团菌是军团菌属的一种好氧性革兰氏阴性细菌，它是军团菌病的主要病原体。最近，鉴定了一种来自嗜肺乳杆菌的核苷三磷酸二磷酸水解酶（NTPDase），并将其称为Lp1NTPDase。它被发现是哺乳动物NTPDase的结构和功能同源物，可催化ATP水解为ADP和ADP水解为AMP。据信其活性有助于肺炎军团菌的毒性。因此，Lp1NTPDase抑制剂被认为是新型抗菌药物。但是，到目前为止，只有弱效化合物可用。在本研究中，建立了用于监测Lp1NTPDase活性的基于毛细管电泳（CE）的酶法。酶促反应在试管中进行，然后通过CE分离底物和产物，随后通过UV分析进行定量。在对该酶进行动力学表征后，研究了一系列与蒽醌染料活性蓝2（一种非选择性ecto-NTPDase抑制剂）结构相关的1-氨基-4-芳基（烷基）基氨基-2-磺基蒽醌衍生物的抑制活性。使用基于CE的酶测定法检测Lp1NTPDase的表达。在1-氨

  DOI：

  10.1016/j.bmc.2016.07.027

文献信息

• The Activities of Sodium Salts of 1-Amino-4-alkylaminoanthraquinone-2-sulfonic Acid in Aqueous Solutions
  作者：Masaru Mitsuishi、Yuzoh Yamaguchi

  DOI：10.1246/bcsj.54.654

  日期：1981.3

  The mean activity coefficients of sodium salts of 1-amino-4-alkylaminoanthraquinone-2-sulfonic acid (alk= Me(MAS), Et, n-Pr, or n-Bu (n-BAS)) in aqueous solutions ranging in concentration from 10−3 to 10−2 mol kg−1 have been determined by means of isopiestic measurements at 50 and 60 °C respectively. It has been found that the mean activity coefficients of these dyes are much smaller than unity, the

  1-氨基-4-烷基氨基蒽醌-2-磺酸钠盐（alk= Me(MAS), Et, n-Pr, or n-Bu (n-BAS)）在不同浓度水溶液中的平均活性系数从 10-3 到 10-2 mol kg-1 已分别通过等压测量在 50 和 60 °C 下确定。已经发现这些染料的平均活性系数远小于1，MAS的系数最大，而n-BAS的系数最小。已经发现这些系数随着染料浓度的增加而降低。对 Miliceivic 处理获得的结果的检查表明，在 60 °C 时，MAS 以二聚体或三聚体形式存在，而其他染料以四聚体形式存在。
• Development of Anthraquinone Derivatives as Ectonucleoside Triphosphate Diphosphohydrolase (NTPDase) Inhibitors With Selectivity for NTPDase2 and NTPDase3
  作者：Younis Baqi、Mahmoud Rashed、Laura Schäkel、Enas M. Malik、Julie Pelletier、Jean Sévigny、Amelie Fiene、Christa E. Müller

  DOI：10.3389/fphar.2020.01282

  日期：——

  Ectonucleoside triphosphate diphosphohydrolases (NTPDases) catalyze the hydrolysis of nucleoside tri- and di-phosphates to mono-phosphates. The products are subsequently hydrolyzed by ecto-5 '-nucleotidase (ecto-5 '-NT) to nucleosides. NTPDase inhibitors have potential as novel drugs, e.g., for the treatment of inflammation, neurodegenerative diseases, and cancer. In this context, a series of anthraquinone derivatives structurally related to the anthraquinone dye reactive blue-2 (RB-2) was synthesized and evaluated as inhibitors of human NTPDases utilizing a malachite green assay. We identified several potent and selective inhibitors of human NTPDase2 and -3. Among the most potent NTPDase2 inhibitors were 1-amino-4-(9-phenanthrylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (20, PSB-16131, IC(50)of 539 nM) and 1-amino-4-(3-chloro-4-phenylsulfanyl)phenylamino-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (48, PSB-2020, IC(50)of 551 nM). The most potent NTPDase3 inhibitors were 1-amino-4-[3-(4,6-dichlorotriazin-2-ylamino)-4-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (42, PSB-1011, IC(50)of 390 nM) and 1-amino-4-(3-carboxy-4-hydroxyphenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (33, PSB-2046, IC(50)of 723 nM). The best NTPDase2 inhibitor 20 showed a non-competitive inhibition type, while the NTPDase3 inhibitor 42 behaved as a mixed-type inhibitor. These potent compounds were found to be selective vs. other NTPDases. They will be useful tools for studying the roles of NTPDase2 and -3 in physiology and under pathological conditions.
• Inhibitors for the bacterial ectonucleotidase Lp1NTPDase from Legionella pneumophila
  作者：Amelie Fiene、Younis Baqi、Enas M. Malik、Patrice Newton、Wenjin Li、Sang-Yong Lee、Elizabeth L. Hartland、Christa E. Müller

  DOI：10.1016/j.bmc.2016.07.027

  日期：2016.9

  catalyzing the hydrolysis of ATP to ADP and ADP to AMP. Its activity is believed to contribute to the virulence of Legionella pneumophila. Therefore Lp1NTPDase inhibitors are considered as novel antibacterial drugs. However, only weakly potent compounds are available so far. In the present study, a capillary electrophoresis (CE)-based enzyme assay for monitoring the Lp1NTPDase activity was established. The

  嗜肺军团菌是军团菌属的一种好氧性革兰氏阴性细菌，它是军团菌病的主要病原体。最近，鉴定了一种来自嗜肺乳杆菌的核苷三磷酸二磷酸水解酶（NTPDase），并将其称为Lp1NTPDase。它被发现是哺乳动物NTPDase的结构和功能同源物，可催化ATP水解为ADP和ADP水解为AMP。据信其活性有助于肺炎军团菌的毒性。因此，Lp1NTPDase抑制剂被认为是新型抗菌药物。但是，到目前为止，只有弱效化合物可用。在本研究中，建立了用于监测Lp1NTPDase活性的基于毛细管电泳（CE）的酶法。酶促反应在试管中进行，然后通过CE分离底物和产物，随后通过UV分析进行定量。在对该酶进行动力学表征后，研究了一系列与蒽醌染料活性蓝2（一种非选择性ecto-NTPDase抑制剂）结构相关的1-氨基-4-芳基（烷基）基氨基-2-磺基蒽醌衍生物的抑制活性。使用基于CE的酶测定法检测Lp1NTPDase的表达。在1-氨
• Efficient and mild deamination procedure for 1-aminoanthraquinones yielding a diverse library of novel derivatives with potential biological activity
  作者：Younis Baqi、Christa E. Müller

  DOI：10.1016/j.tetlet.2012.09.011

  日期：2012.12

  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.