3,4-Dihydro-6-hydroxy-2-[2-(4-phenyl-1-piperidinyl)ethyl]-1(2H)naphthalenone | 212259-30-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3,4-Dihydro-6-hydroxy-2-[2-(4-phenyl-1-piperidinyl)ethyl]-1(2H)naphthalenone
• 英文别名: 6-hydroxy-2-[2-(4-phenylpiperidin-1-yl)ethyl]-3,4-dihydro-2H-naphthalen-1-one
• CAS: 212259-30-8
• 化学式: C₂₃H₂₇NO₂
• 分子量: 349.473
• InChiKey: JSPIBOLFEHIRMC-UHFFFAOYSA-N

物化性质

• 沸点：
  545.4±50.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-Dihydro-6-hydroxy-2-[2-(4-phenyl-1-piperidinyl)ethyl]-1(2H)naphthalenone 、 alkaline earth salt of/the/ methylsulfuric acid 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[2-(4-phenylpiperidin-1-yl)ethyl]-6-(pyridin-4-ylmethoxy)-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Tetrahydronaphthalene-derived amino alcohols and amino ketones as potent and selective inhibitors of the delayed rectifier potassium current IKs

  摘要：

  Class III anti-arrhythmic drugs (e.g., dofetilide) prolong cardiac action potential duration (APD) by blocking the fast component of the delayed rectifier potassium current (I-Kr). The block of I-Kr can result in life threatening ventricular arrhythmias (i.e., torsades de pointes). Unlike I-Kr, the role of the slow component of the delayed rectifier potassium current (I-Ks) becomes significant only at faster heart rate. Therefore selective blockers Of I-Ks could prolong APD with a reduced propensity to cause proarrhythmic side effects. This report describes structure-activity relationships (SARs) of a series of I-Ks inhibitors derived from 6-alkoxytetralones with good in vitro activity (IC50 > 30 nM) and up to 40-fold I-Ks/I-Kr selectivity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.003
• 作为产物：
  描述：

  3,4-Dihydro-6-(phenylmethoxy)-2-[2-(4-phenyl-1-piperidinyl)ethyl]-1(2H)naphthalenone 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以88%的产率得到3,4-Dihydro-6-hydroxy-2-[2-(4-phenyl-1-piperidinyl)ethyl]-1(2H)naphthalenone
  参考文献：
  名称：

  Tetrahydronaphthalene-derived amino alcohols and amino ketones as potent and selective inhibitors of the delayed rectifier potassium current IKs

  摘要：

  Class III anti-arrhythmic drugs (e.g., dofetilide) prolong cardiac action potential duration (APD) by blocking the fast component of the delayed rectifier potassium current (I-Kr). The block of I-Kr can result in life threatening ventricular arrhythmias (i.e., torsades de pointes). Unlike I-Kr, the role of the slow component of the delayed rectifier potassium current (I-Ks) becomes significant only at faster heart rate. Therefore selective blockers Of I-Ks could prolong APD with a reduced propensity to cause proarrhythmic side effects. This report describes structure-activity relationships (SARs) of a series of I-Ks inhibitors derived from 6-alkoxytetralones with good in vitro activity (IC50 > 30 nM) and up to 40-fold I-Ks/I-Kr selectivity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.003

文献信息

• US6048877A
  申请人：——

  公开号：US6048877A

  公开（公告）日：2000-04-11