1-氨基-9,10-二氧-4-((5,6,7,8-四氢萘-2-基)氨基)-9,10-二氢蒽-2-磺酸钠 | 1363419-31-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1-氨基-9,10-二氧-4-((5,6,7,8-四氢萘-2-基)氨基)-9,10-二氢蒽-2-磺酸钠
• 英文名称: sodium 1-amino-9,10-dioxo-4-((5,6,7,8-tetrahydronaphthalen-2-yl)amino)-9,10-dihydroanthracene-2-sulfonate
• 英文别名: GoSlo-SR-5-69；GoSlo SR 5-69；sodium;1-amino-9,10-dioxo-4-(5,6,7,8-tetrahydronaphthalen-2-ylamino)anthracene-2-sulfonate
• CAS: 1363419-31-1
• 化学式: C₂₄H₁₉N₂O₅S*Na
• 分子量: 470.481
• InChiKey: JOJJZTFRBZWSBX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.57
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 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-9,10-二氧-4-((5,6,7,8-四氢萘-2-基)氨基)-9,10-二氢蒽-2-磺酸钠 在 盐酸 、 sodium nitrite 、 锌 作用下， 以 水 、 乙醇 为溶剂， 反应 1.16h， 以96%的产率得到9,10-dioxo-4-((5,6,7,8-tetrahydronaphthalen-2-yl)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：

  5,6,7,8-四氢-2-萘胺 、 sodium 1-amino-4-bromoanthraquinone-2-sulfonate 在 铜 作用下， 以 aq. phosphate buffer 为溶剂， 以76%的产率得到1-氨基-9,10-二氧-4-((5,6,7,8-四氢萘-2-基)氨基)-9,10-二氢蒽-2-磺酸钠
  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

文献信息

• [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。
• 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.
• US9877940B2
  申请人：——

  公开号：US9877940B2

  公开（公告）日：2018-01-30
• Development of GoSlo-SR-5-69, a potent activator of large conductance Ca2+-activated K+ (BK) channels
  作者：Subhrangsu Roy、Roddy J. Large、Adebola Morayo Akande、Aravind Kshatri、Tim I. Webb、Carmen Domene、Gerard P. Sergeant、Noel G. McHale、Keith D. Thornbury、Mark A. Hollywood

  DOI：10.1016/j.ejmech.2014.01.035

  日期：2014.3

  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.