1-(2-羟基-4-(2-羟基乙基)苯基)乙烷-1,2-二醇 | 188110-00-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 1-(2-羟基-4-(2-羟基乙基)苯基)乙烷-1,2-二醇
• 英文名称: 1-[2-Hydroxy-4-(2-hydroxyethyl)phenyl]ethane-1,2-diol
• CAS: 188110-00-1
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: JXFWKRCHQRRRTL-UHFFFAOYSA-N

物化性质

• 沸点：
  387.5±30.0 °C(Predicted)
• 密度：
  1.350±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-羟基-4-(2-羟基乙基)苯基)乙烷-1,2-二醇 在 吡啶盐酸盐 、 lithium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙二醇 、 乙腈 为溶剂， 反应 50.5h， 生成 A 80426
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of N-(Arylethyl)-N-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-N-methylamines Possessing Dual 5-HT Uptake Inhibiting and α₂-Antagonistic Activities

  摘要：

  In search of an alpha(2)-antagonist/5-HT uptake inhibitor as a potential new class of antidepressant with a more rapid onset of action, compound 3 was prepared and observed to possess high affinity for the alpha(2)-receptor (K-i = 6.71 nM) and the 5-HT uptake site (20.6 nM). A series of tertiary amine analogs of 3 were synthesized and assayed for their affinity at both the alpha(2)-receptor and the 5-HT uptake site. The structure-activity relationship reveals that a variety of structural modifications to the arylethyl fragment are possible with retention of this dual activity. On the tetralin portion, 5-OMe substitution and the (R) stereochemistry at C-l are optimal with alternate substitutions producing compounds retaining high affinity for the alpha(2)-receptor but lacking affinity for the 5-HT uptake site. Data for several rigidified 5-O-alkyl analogs suggests that the favored orientation of the oxygen lone pairs may be away from the g-position of the tetralin.

  DOI：

  10.1021/jm960723m
• 作为产物：
  描述：

  3-羟基苯乙酸 在 硼烷四氢呋喃络合物 、 硫酸 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 11.5h， 生成 1-(2-羟基-4-(2-羟基乙基)苯基)乙烷-1,2-二醇
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of N-(Arylethyl)-N-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-N-methylamines Possessing Dual 5-HT Uptake Inhibiting and α₂-Antagonistic Activities

  摘要：

  In search of an alpha(2)-antagonist/5-HT uptake inhibitor as a potential new class of antidepressant with a more rapid onset of action, compound 3 was prepared and observed to possess high affinity for the alpha(2)-receptor (K-i = 6.71 nM) and the 5-HT uptake site (20.6 nM). A series of tertiary amine analogs of 3 were synthesized and assayed for their affinity at both the alpha(2)-receptor and the 5-HT uptake site. The structure-activity relationship reveals that a variety of structural modifications to the arylethyl fragment are possible with retention of this dual activity. On the tetralin portion, 5-OMe substitution and the (R) stereochemistry at C-l are optimal with alternate substitutions producing compounds retaining high affinity for the alpha(2)-receptor but lacking affinity for the 5-HT uptake site. Data for several rigidified 5-O-alkyl analogs suggests that the favored orientation of the oxygen lone pairs may be away from the g-position of the tetralin.

  DOI：

  10.1021/jm960723m

文献信息

• Structure−Activity Studies for a Novel Series of <i>N</i>-(Arylethyl)-<i>N</i>-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)-<i>N</i>-methylamines Possessing Dual 5-HT Uptake Inhibiting and α₂-Antagonistic Activities
  作者：Michael D. Meyer、Arthur A. Hancock、Karin Tietje、Kevin B. Sippy、Rajnandan Prasad、David M. Stout、David L. Arendsen、B. Greg Donner、William A. Carroll

  DOI：10.1021/jm960723m

  日期：1997.3.1

  In search of an alpha(2)-antagonist/5-HT uptake inhibitor as a potential new class of antidepressant with a more rapid onset of action, compound 3 was prepared and observed to possess high affinity for the alpha(2)-receptor (K-i = 6.71 nM) and the 5-HT uptake site (20.6 nM). A series of tertiary amine analogs of 3 were synthesized and assayed for their affinity at both the alpha(2)-receptor and the 5-HT uptake site. The structure-activity relationship reveals that a variety of structural modifications to the arylethyl fragment are possible with retention of this dual activity. On the tetralin portion, 5-OMe substitution and the (R) stereochemistry at C-l are optimal with alternate substitutions producing compounds retaining high affinity for the alpha(2)-receptor but lacking affinity for the 5-HT uptake site. Data for several rigidified 5-O-alkyl analogs suggests that the favored orientation of the oxygen lone pairs may be away from the g-position of the tetralin.