2-[2-Hydroxy-3-(1H-indol-4-yloxy)-propylamino]-2-methyl-propan-1-ol | 110505-83-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-[2-Hydroxy-3-(1H-indol-4-yloxy)-propylamino]-2-methyl-propan-1-ol
• 英文别名: 2-[[2-hydroxy-3-(1H-indol-4-yloxy)propyl]amino]-2-methylpropan-1-ol
• CAS: 110505-83-4
• 化学式: C₁₅H₂₂N₂O₃
• 分子量: 278.351
• InChiKey: BFFLSLPWRACIBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  77.5
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羟基吲哚 在 1,4-二氧六环 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 58.0h， 生成 2-[2-Hydroxy-3-(1H-indol-4-yloxy)-propylamino]-2-methyl-propan-1-ol
  参考文献：
  名称：

  Synthesis and .beta.-adrenergic receptor blocking potency of 1-(substituted amino)-3-(4-indolyloxy)propan-2-ols

  摘要：

  Although (-)-[125I]iodopindolol (IPIN) can be used to label beta-adrenergic receptors in the central nervous system in vivo, use of this ligand for receptor imaging studies in humans may be limited due to its relatively poor penetration into the brain. As a first step toward the development of radioligands for imaging studies, we report the synthesis and measurement of in vitro binding affinity to beta-receptors of a series of 1-(substituted amino)-3-(4-indolyloxy)-propan-2-ol derivatives. The synthesized compounds vary widely in their lipophilicity as measured by their distribution coefficients between phosphate buffer and octanol at pH 7.4. The affinity of these compounds for beta-receptors, as measured by their inhibition of binding of IPIN to rat cortical and cerebellar membranes in vitro, ranges from 2- to 100-fold less potent than pindolol; the most potent compounds have Ki values of 2-5 nM. The radiolabeled analogues of some of these compounds may prove useful for receptor imaging studies.

  DOI：

  10.1021/jm00158a035

文献信息

• TEJANI-BUTT SH. M.; BRUNSWICK D. J., J. MED. CHEM., 29,(1986) N 8, 1524-1527
  作者：TEJANI-BUTT SH. M.、 BRUNSWICK D. J.

  DOI：——

  日期：——
• Synthesis and .beta.-adrenergic receptor blocking potency of 1-(substituted amino)-3-(4-indolyloxy)propan-2-ols
  作者：Shanaz M. Tejani-Butt、David J. Brunswick

  DOI：10.1021/jm00158a035

  日期：1986.8

  Although (-)-[125I]iodopindolol (IPIN) can be used to label beta-adrenergic receptors in the central nervous system in vivo, use of this ligand for receptor imaging studies in humans may be limited due to its relatively poor penetration into the brain. As a first step toward the development of radioligands for imaging studies, we report the synthesis and measurement of in vitro binding affinity to beta-receptors of a series of 1-(substituted amino)-3-(4-indolyloxy)-propan-2-ol derivatives. The synthesized compounds vary widely in their lipophilicity as measured by their distribution coefficients between phosphate buffer and octanol at pH 7.4. The affinity of these compounds for beta-receptors, as measured by their inhibition of binding of IPIN to rat cortical and cerebellar membranes in vitro, ranges from 2- to 100-fold less potent than pindolol; the most potent compounds have Ki values of 2-5 nM. The radiolabeled analogues of some of these compounds may prove useful for receptor imaging studies.