2-Anthracenesulfonic acid,1-amino-4-[(4-amino-3-sulfophenyl)amino]-9,10-dihydro-9,10-dioxo-,disodium salt | 15827-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-Anthracenesulfonic acid,1-amino-4-[(4-amino-3-sulfophenyl)amino]-9,10-dihydro-9,10-dioxo-,disodium salt
• 英文别名: disodium 1-amino-4-(4-amino-3-sulfophenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate；1-amino-4-[4-amino-3-sulfophenylamino]-9,10-dioxo-9,10 dihydroanthracene-2-sulfonic acid disodium salt；Natrium-1-amino-4,4'-aminophenyl-amino-anthrachinon-2,3'-disulfonat
• CAS: 15827-21-1；32866-11-8；116679-68-6
• 化学式: C₂₀H₁₃N₃O₈S₂*2Na
• 分子量: 533.45
• InChiKey: LGGVGARQLUXCOF-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -1.82
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  212.61
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-Anthracenesulfonic acid,1-amino-4-[(4-amino-3-sulfophenyl)amino]-9,10-dihydro-9,10-dioxo-,disodium salt 、 2-溴嘧啶 以 水 、 丙酮 为溶剂， 反应 72.0h， 以97%的产率得到disodium 1-amino-4-[4-([1,3]diazine-2-ylamino)-3-sulfophenylamino]-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate
  参考文献：
  名称：

  Novel P2Y12 receptor antagonists

  摘要：

  本发明涉及化合物的I式，其中A和B分别为CH2、O、S、NH、C=O、C=NH、C=S或C=N-OH；X为NH、O、S、C=O或CH2，R1-R5如权利要求书中所定义，这些化合物是P2Y12受体拮抗剂，可用于治疗、缓解和/或预防与P2Y12受体功能相关的疾病和紊乱，以及包含这些化合物的药物组合物和制备这些化合物的方法。本发明进一步涉及使用这些化合物，单独或与其他治疗剂联合使用，用于缓解、预防和/或治疗疾病和紊乱，特别是作为抗血栓药物用于抑制血小板聚集。

  公开号：

  EP1967513A1
• 作为产物：
  描述：

  sodium 1-amino-4-bromoanthraquinone-2-sulfonate 、 sodium 2,5-diaminobenzenesulfonate 在 copper(l) chloride 作用下， 以 水 为溶剂， 反应 4.0h， 以67%的产率得到2-Anthracenesulfonic acid,1-amino-4-[(4-amino-3-sulfophenyl)amino]-9,10-dihydro-9,10-dioxo-,disodium salt
  参考文献：
  名称：

  活性染料、活性染料墨水及其制备方法和应用

  摘要：

  本发明公开了一种基于双吖丙啶基团的活性染料及其制备方法和使用方法；本发明还同时公开了利用上述基于双吖丙啶基团的活性染料制备而得的数码喷墨印花用活性染料墨水，包括14～16％活性染料、9～11％表面活性剂、19～21％多元醇、9～11％尿素、0.8～1.2％分散剂、0.15～0.25％防腐剂、0.15～0.25％pH调节剂、余量为去离子水。本发明还同时公开了该数码喷墨印花用活性染料墨水的使用方法。本发明的基于双吖丙啶基团的活性染料可与棉纤维、蚕丝纤维发生化学反应，形成共价键而牢固结合。

  公开号：

  CN112341838B

文献信息

• Structure–activity relationships of novel P2-receptor antagonists structurally related to Reactive Blue 2
  作者：Markus Glänzel、Ralph Bültmann、Klaus Starke、August W. Frahm

  DOI：10.1016/j.ejmech.2005.07.007

  日期：2005.12

  we have shown that Reactive Blue 2 (RB 2), one of the most widely used P2-receptor antagonists, displays only moderate affinity and does not discriminate between native P2X- and P2Y-receptor subtypes. In the present study we have pharmacologically evaluated a series of 15 synthesized and re-evaluated four commercially obtained and chromatographically purified RB 2 type anthraquinone derivatives on

  核苷酸的P2膜受体代表了实验药理学和药物研究的重要目标。在较早的出版物中，我们显示了反应最广泛的P2受体拮抗剂之一，反应性蓝2（RB 2）仅显示中等亲和力，不能区分天然P2X和P2Y受体亚型。在本研究中，我们已经通过药理学评估了一系列15种合成并重新评估的4种商业获得和色谱纯化的RB 2型蒽醌衍生物对α，β-亚甲基ATP（α，β）引起的大鼠输精管（RVD）收缩的影响。 -meATP）介导，并由腺苷5'-O-（2-硫代二磷酸）（ADPbetaS）诱发的，由P2Y1样受体介导的卡巴胆碱收缩的豚鼠带状大肠杆菌（GPTC）松弛。根据结构-活性关系（SAR）得出的结论是，芳香族π电子系统的疏水相互作用，与氮作为供体和受体原子的氢键，特别是阴离子磺酸盐基团的位置，构象距离和数量都很大。对于两种天然P2受体亚型的阻断具有重要意义。我们还发现了与RB 2相比具有更高亲和力和更高亚型选择性的新型可逆拮抗剂。特别是1-amino-4-
• 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.
• 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.