2-[2-oxo-2-(4-phenylpiperidin-1-yl)ethyl]-6-phenylmethoxy-3,4-dihydro-2H-naphthalen-1-one | 667900-14-3

• 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: 2-[2-oxo-2-(4-phenylpiperidin-1-yl)ethyl]-6-phenylmethoxy-3,4-dihydro-2H-naphthalen-1-one
• CAS: 667900-14-3
• 化学式: C₃₀H₃₁NO₃
• 分子量: 453.581
• InChiKey: VFZHAZYDXSIRHK-UHFFFAOYSA-N

物化性质

• 沸点：
  674.1±55.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[2-oxo-2-(4-phenylpiperidin-1-yl)ethyl]-6-phenylmethoxy-3,4-dihydro-2H-naphthalen-1-one 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 四丁基碘化铵 、 potassium carbonate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 叔丁醇 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：

  6-羟基-1-四氢萘酮 在 N-甲基吗啉 、 六甲基磷酰三胺 、 氢氧化钾 、 potassium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[2-oxo-2-(4-phenylpiperidin-1-yl)ethyl]-6-phenylmethoxy-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

文献信息

• Tetrahydronaphthalene-derived amino alcohols and amino ketones as potent and selective inhibitors of the delayed rectifier potassium current IKs
  作者：Saleem Ahmad、Lidia Doweyko、Aaila Ashfaq、Francis N. Ferrara、Sharon N. Bisaha、Joan B. Schmidt、John DiMarco、Mary Lee Conder、Tonya Jenkins-West、Diane E. Normandin、Anita D. Russell、Mark A. Smith、Paul C. Levesque、Nicholas J. Lodge、John Lloyd、Philip D. Stein、Karnail S. Atwal

  DOI：10.1016/j.bmcl.2003.10.003

  日期：2004.1

  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.