1-氨基-4-(1-萘基)氨基蒽醌-2-磺酸钠盐 | 1052089-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1-氨基-4-(1-萘基)氨基蒽醌-2-磺酸钠盐
• 英文名称: sodium 1-amino-4-(1-naphthylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate
• 英文别名: sodium 1-amino-4-[1-naphthylamino]-9,10-dioxo-9,10 dihydroanthracene-2-sulfonate；sodium 1-amino-4-(naphthalen-1-ylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate；1-Amino-4-(1-naphthyl)aminoanthraquinone-2-sulfonicacidsodiumsalt；sodium;1-amino-4-(naphthalen-1-ylamino)-9,10-dioxoanthracene-2-sulfonate
• CAS: 1052089-16-3
• 化学式: C₂₄H₁₅N₂O₅S*Na
• 分子量: 466.449
• InChiKey: BLOBABILSRPNHR-UHFFFAOYSA-M

物化性质

• 溶解度：
  在 DMSO 中溶解度为 100 mM，在乙醇中溶解度为 50 mM

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• 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

• 作为反应物：
  描述：

  1-氨基-4-(1-萘基)氨基蒽醌-2-磺酸钠盐 在 盐酸 、 水 、 sodium nitrite 、 乙醇 、 锌 作用下， 反应 0.01h， 以89%的产率得到4-(1-naphthylamino)-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 、 1-萘胺 在 铜 作用下， 以 aq. phosphate buffer 为溶剂， 生成 1-氨基-4-(1-萘基)氨基蒽醌-2-磺酸钠盐
  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

• 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
• [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。
• 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.
• 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).
• 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.