1-氨基-9,10-二氢代-4-[(2-甲苯基)氨基]-9,10-二氧代-2-蒽磺酸钠盐 | 25492-67-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1-氨基-9,10-二氢代-4-[(2-甲苯基)氨基]-9,10-二氧代-2-蒽磺酸钠盐
• 英文名称: sodium 1-amino-4-(2-methylphenylamino)-9,10-dioxo-9,10-dihydroanthracene 2-sulfonate
• 英文别名: 2-Anthracenesulfonic acid, 1-amino-9,10-dihydro-4-[(2-methylphenyl)amino]-9,10-dioxo-, monosodium salt；sodium;1-amino-4-(2-methylanilino)-9,10-dioxoanthracene-2-sulfonate
• CAS: 25492-67-5
• 化学式: C₂₁H₁₅N₂O₅S*Na
• 分子量: 430.416
• InChiKey: JUUHQEFCLDKFAL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.0
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 海关编码：
  2922399090

反应信息

• 作为产物：
  描述：

  sodium 1-amino-4-bromoanthraquinone-2-sulfonate 、 邻甲苯胺 在 铜 作用下， 以 aq. phosphate buffer 为溶剂， 以23%的产率得到1-氨基-9,10-二氢代-4-[(2-甲苯基)氨基]-9,10-二氧代-2-蒽磺酸钠盐
  参考文献：
  名称：

  1-氨基-4-(苯基氨基)蒽醌-2-磺酸钠衍生物作为RANKL诱导的破骨细胞生成的新型抑制剂的开发

  摘要：

  合成了一系列 1-氨基-4-（苯基氨基）蒽醌-2-磺酸钠衍生物，并使用 TRAP 染色试验评估了对破骨细胞的抑制作用。其中，两种化合物 LCCY-13 和 LCCY-15 剂量依赖性地抑制核因子-κB 配体（RANKL）诱导的破骨细胞形成的受体激活剂。此外，对 RAW264.7 细胞的细胞毒性试验表明，这些化合物对破骨细胞骨吸收的抑制不是它们的细胞毒性的结果。此外，通过使用免疫荧光分析包括对细胞核中 NFATc1 表达水平的特异性抑制，进一步证实了化合物 LCCY-13 和 LCCY-15 的抑制活性。此外，根据凹坑形成试验，LCCY-13 和 LCCY-15 还显着减弱了破骨细胞的骨吸收活性。因此，

  DOI：

  10.1002/ardp.201500475

文献信息

• 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
• Development of Potent and Selective Antagonists for the UTP-Activated P2Y₄ Receptor
  作者：Muhammad Rafehi、Enas M. Malik、Alexander Neumann、Aliaa Abdelrahman、Theodor Hanck、Vigneshwaran Namasivayam、Christa E. Müller、Younis Baqi

  DOI：10.1021/acs.jmedchem.7b00030

  日期：2017.4.13

  nM, selectivity versus other P2Y receptor subtypes, and is thought to act as an allosteric antagonist. A receptor homology model was built and docking studies were performed to analyze ligand–receptor interactions. Compound 64 (PSB-1699, sodium 1-amino-4-[4-(3-pyridin-3-ylmethylthio)phenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate) represents the most selective P2Y4 receptor antagonist known

  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
• 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.
• Discovery of Potent Competitive Antagonists and Positive Modulators of the P2X2 Receptor
  作者：Younis Baqi、Ralf Hausmann、Christiane Rosefort、Jürgen Rettinger、Günther Schmalzing、Christa E. Müller

  DOI：10.1021/jm1012193

  日期：2011.2.10

  Evaluation and optimization of anthraquinone derivatives related to Reactive Blue 2 at P2X2 receptors yielded the first potent and selective P2X2 receptor antagonists. The compounds were tested for inhibition of ATP (10 mu M) mediated currents in Xenopus oocytes expressing the rat P2X2 receptor. The most potent antagonists were sodium 1-amino-4-[3-(4,6-dichloro[1,3,5]triazine-2-ylamino)phenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (63, PSB-10211, IC50 86 nM) and disodium 1-amino-4-[3-(4,6-dichloro[1,3,5]triazine-2-ylamino)-4-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (57, PSB-1011, IC50 79 nM). Compound 57 exhibited a competitive mechanism of action (pA(2) 7.49). It was > 100-fold selective versus P2X4, P2X7, and several investigated P2Y receptor sub-types (P2Y(2,4,6,12)); selectivity versus P2X1 and P2X3 receptors was moderate ( > 5-fold). Compound 57 was > 13-fold more potent at the homomeric P2X2 than at the heteromeric P2X2/3 receptor. Several anthraquinone derivatives were found to act as positive modulators of ATP effects at P2X2 receptors, for example, sodium 1-amino-4-(3-phenoxyphenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate (51, PSB-10129, EC50 489 nM), which led to about a 3-fold increase in the ATP-elicited current.