5-Amino-6-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-naphthalen-1-ol | 615248-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-Amino-6-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-naphthalen-1-ol
• 英文别名: 5-Amino-6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)naphthalen-1-ol
• CAS: 615248-55-0
• 化学式: C₁₃H₉F₆NO₂
• 分子量: 325.21
• InChiKey: KWWJHYFLSKDMSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  66.5
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 5-Amino-6-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-naphthalen-1-ol 生成 2-Methyl-4,4-bis-trifluoromethyl-4H-naphtho[1,2-d][1,3]oxazin-7-ol 、 N-[5-Hydroxy-2-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-naphthalen-1-yl]-acetamide
  参考文献：
  名称：

  Structure–activity relationship of a novel class of naphthyl amide KATP channel openers

  摘要：

  We have discovered a novel series of N-[2-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-naphthalen-1-yl] amides that are potent openers of K-ATP channels and investigated structure-activity relationships (SAR) around the 1,2-disubstituted naphthyl core. A-151892, a prototype compound of this series, was found to be a potent and efficacious potassium channel opener in vitro in transfected Kir6.2/SUR2B cells and pig bladder strips. Additionally, A-151892 was found to selectively inhibit unstable bladder contractions in vivo in an obstructed rat model of myogenic bladder function. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00205-1
• 作为产物：
  描述：

  1-氨基-5-萘酚 、 六氟丙酮 在 对甲苯磺酸 作用下， 生成 5-Amino-6-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-naphthalen-1-ol
  参考文献：
  名称：

  Structure–activity relationship of a novel class of naphthyl amide KATP channel openers

  摘要：

  We have discovered a novel series of N-[2-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-naphthalen-1-yl] amides that are potent openers of K-ATP channels and investigated structure-activity relationships (SAR) around the 1,2-disubstituted naphthyl core. A-151892, a prototype compound of this series, was found to be a potent and efficacious potassium channel opener in vitro in transfected Kir6.2/SUR2B cells and pig bladder strips. Additionally, A-151892 was found to selectively inhibit unstable bladder contractions in vivo in an obstructed rat model of myogenic bladder function. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00205-1

文献信息

• Naphthalene amides as potassium channel openers
  申请人：——

  公开号：US20030199578A1

  公开（公告）日：2003-10-23

  The present invention relates to compounds and their ability to act as potassium channel openers.

  本发明涉及化合物及其作为钾通道开放剂的能力。
• Structure–activity relationship of a novel class of naphthyl amide KATP channel openers
  作者：Sean C Turner、William A Carroll、Tammie K White、Michael E Brune、Steven A Buckner、Murali Gopalakrishnan、Adebola Fabiyi、Michael J Coghlan、Victoria E Scott、Neil A Castle、Anthony V Daza、Ivan Milicic、James P Sullivan

  DOI：10.1016/s0960-894x(03)00205-1

  日期：2003.5

  We have discovered a novel series of N-[2-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-naphthalen-1-yl] amides that are potent openers of K-ATP channels and investigated structure-activity relationships (SAR) around the 1,2-disubstituted naphthyl core. A-151892, a prototype compound of this series, was found to be a potent and efficacious potassium channel opener in vitro in transfected Kir6.2/SUR2B cells and pig bladder strips. Additionally, A-151892 was found to selectively inhibit unstable bladder contractions in vivo in an obstructed rat model of myogenic bladder function. (C) 2003 Elsevier Science Ltd. All rights reserved.