sodium 1-amino-4-(3-(trifluoromethyl)phenylamino)-9,10-dioxo-9,10-dihydroanthracene 2-sulfonate | 1261946-89-7

• 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-(3-(trifluoromethyl)phenylamino)-9,10-dioxo-9,10-dihydroanthracene 2-sulfonate
• 英文别名: sodium-1-amino-4-((3-trifluoromethylphenyl)amino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate；sodium 1-amino-4-(3-trifluoromethylphenylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonate；GoSlo-SR-5-6；sodium 1-amino-9,10-dioxo-4-(3-(trifluoromethyl)phenylamino)-9,10-dihydroanthracene-2-sulfonate；1-Amino-4-[3-(trifluoromethyl)phenylamino]-9,10-dihydro-9,10-dioxoanthracene-2-sulfonic acid sodium salt；sodium;1-amino-9,10-dioxo-4-[3-(trifluoromethyl)anilino]anthracene-2-sulfonate
• CAS: 1261946-89-7
• 化学式: C₂₁H₁₂F₃N₂O₅S*Na
• 分子量: 484.388
• InChiKey: XWXBWOXCLOZHNC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  33
• 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：
  10

反应信息

• 作为反应物：
  描述：

  sodium 1-amino-4-(3-(trifluoromethyl)phenylamino)-9,10-dioxo-9,10-dihydroanthracene 2-sulfonate 在 盐酸 、 sodium nitrite 、 锌 作用下， 以 水 、 乙醇 为溶剂， 反应 1.16h， 以98%的产率得到9,10-dioxo-4-((3-(trifluoromethyl)phenyl)amino)-9,10-dihydroanthracene-2-sulfonic acid
  参考文献：
  名称：

  Development of GoSlo-SR-5-69, a potent activator of large conductance Ca2+-activated K+ (BK) channels

  摘要：

  We have designed, synthesised and characterised the effects of a number of novel anthraquinone derivatives and assessed their effects on large conductance, Ca2+ activated K+ (BK) channels recorded from rabbit bladder smooth muscle cells using the excised, inside/out configuration of the patch clamp technique. These compounds are members of the GoSlo-SR family of compounds, which potently open BK channels and shift the voltage required for half maximal activation (V-1/2) negatively. The efficacy of the anilinoanthraquinone derivatives was enhanced when the size of ring D was increased, since the cyclopentane and cyclohexane derivatives shifted the V-1/2, by -24+/-6 mV and -54+/-8 mV, respectively, whereas the cycloheptane and cyclooctane derivatives shifted the V-1/2 by -61+/-6 mV and -106+/-6 mV. To examine if a combination of hydrophobicity and steric bulking of this region further enhanced their ability to open BK channels, we synthesised a number of naphthalene and tetrahydro-naphthalene derivatives. The tetrahydro-2-naphthalene derivative GoSlo-SR-5-69 was the most potent and efficacious of the series since it was able to shift the activation V-1/2 by greater than 100 mV when applied at a concentration of 1 mu M and had an EC50 of 251 nM, making it one of the most potent and efficacious BK channel openers synthesised to date. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.035
• 作为产物：
  描述：

  sodium 1-amino-4-bromoanthraquinone-2-sulfonate 、 间氨基三氟甲苯 在 铜 作用下， 以 aq. phosphate buffer 为溶剂， 以21%的产率得到sodium 1-amino-4-(3-(trifluoromethyl)phenylamino)-9,10-dioxo-9,10-dihydroanthracene 2-sulfonate
  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

• Anthraquinone compounds and their uses
  申请人：Dundalk Institute of Technology

  公开号：EP2439200A1

  公开（公告）日：2012-04-11

  This invention relates to compounds 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; for example, BK Channel activity. The compounds of the present invention find utility in the treatment such as urinary incontinence, irritable bowel syndrome, diabetes and arterial hypertension, cardiovascular diseases including myocardial infarction, erectile dysfunction and airway constriction.

  本发明涉及包含取代或未取代蒽醌的化合物，或其盐或异构体，用于治疗由或与离子通道活性失调引起的疾病；例如，BK通道活性。本发明的化合物在治疗尿失禁、肠易激综合征、糖尿病和动脉高压、心血管疾病包括心肌梗死、勃起功能障碍和气道收缩等方面具有实用价值。
• [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。
• 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.
• ANTHRAQUINONE COMPOUNDS AND THEIR USES
  申请人：Dundalk Institute of Technology

  公开号：EP2616449A1

  公开（公告）日：2013-07-24
• Anthraquinone Compounds and Their Uses
  申请人：McHale Noel

  公开号：US20130296588A1

  公开（公告）日：2013-11-07

  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 partial hypertension; myocardial infarction; faecal incontinence; constipation; gastro oesophageal reflux; impaired gastrointenstinal passage; urinary incontinence; erectile dysfunction; and asthma.