(2S)-2-[((2-(2,6-dimethoxyphenoxy)ethyl)amino)methyl]-2,3,6,7,8,9-hexahydronaphtho[2,3-b][1,4]dioxine | 753023-12-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (2S)-2-[((2-(2,6-dimethoxyphenoxy)ethyl)amino)methyl]-2,3,6,7,8,9-hexahydronaphtho[2,3-b][1,4]dioxine
• 英文别名: 2-(2,6-dimethoxyphenoxy)-N-[[(3S)-2,3,6,7,8,9-hexahydrobenzo[g][1,4]benzodioxin-3-yl]methyl]ethanamine
• CAS: 753023-12-0
• 化学式: C₂₃H₂₉NO₅
• 分子量: 399.487
• InChiKey: OTIFDGAFLVKAPS-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  58.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-2-[((2-(2,6-dimethoxyphenoxy)ethyl)amino)methyl]-2,3,6,7,8,9-hexahydronaphtho[2,3-b][1,4]dioxine 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以0.634 g的产率得到[2-(2,6-Dimethoxy-phenoxy)-ethyl]-[(S)-1-(2,3,6,7,8,9-hexahydro-naphtho[2,3-b][1,4]dioxin-2-yl)methyl]-amine; hydrochloride
  参考文献：
  名称：

  Structure–affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101

  摘要：

  A number of enantiomeric pairs of naphthodioxane, tetrahydronaphthodioxane and naphthoxy analogues of WB-4101 (1) were designed and synthesized in order to improve the selectivity profile of the parent compound, hopefully in favour of the alpha(1a)-AR with respect to the other two alpha(1), subtypes and the 5-HT1A receptor. The new compounds 2-8 and, in addition, the two enantiomers of 1 were tested in binding assays on the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptor. Two of them, namely the naphtho- and tetrahydronaphthodioxane derivatives (S)-2 and (S)-3, showed lower, but significantly more specific alpha(1a), affinity than (S)-1, while the two enantiomers of the 2-methoxy-1-naphthoxy analogue 6 maintained most of the very high alpha(1a) affinity of (S)-1 and its alpha(1a) versus alpha(1b) selectivity slightly increasing the alpha(1a)/alpha(1d) and alpha(1a)/5HT(1A) affinity ratios. The SAR data were evaluated in the light of known alpha(1), subtype pharmacophores and of the alpha(1a)-AR binding mode of WB-4101 resultant from literature mutagenesis studies disclosing some interesting consonances with these models. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.040
• 作为产物：
  描述：

  3-benzyloxy-5,6,7,8-tetrahydro-2-naphthol 在 palladium on activated charcoal 氢氧化钾 、 TEA 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 异丙醇 、 丙酮 为溶剂， 反应 85.0h， 生成 (2S)-2-[((2-(2,6-dimethoxyphenoxy)ethyl)amino)methyl]-2,3,6,7,8,9-hexahydronaphtho[2,3-b][1,4]dioxine
  参考文献：
  名称：

  Structure–affinity studies for a novel series of homochiral naphtho and tetrahydronaphtho analogues of α1 antagonist WB-4101

  摘要：

  A number of enantiomeric pairs of naphthodioxane, tetrahydronaphthodioxane and naphthoxy analogues of WB-4101 (1) were designed and synthesized in order to improve the selectivity profile of the parent compound, hopefully in favour of the alpha(1a)-AR with respect to the other two alpha(1), subtypes and the 5-HT1A receptor. The new compounds 2-8 and, in addition, the two enantiomers of 1 were tested in binding assays on the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptor. Two of them, namely the naphtho- and tetrahydronaphthodioxane derivatives (S)-2 and (S)-3, showed lower, but significantly more specific alpha(1a), affinity than (S)-1, while the two enantiomers of the 2-methoxy-1-naphthoxy analogue 6 maintained most of the very high alpha(1a) affinity of (S)-1 and its alpha(1a) versus alpha(1b) selectivity slightly increasing the alpha(1a)/alpha(1d) and alpha(1a)/5HT(1A) affinity ratios. The SAR data were evaluated in the light of known alpha(1), subtype pharmacophores and of the alpha(1a)-AR binding mode of WB-4101 resultant from literature mutagenesis studies disclosing some interesting consonances with these models. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.040