1-(3,4-dimethoxy-benzyl)-6-methoxy-2,3,4,9-tetrahydro-1H-β-carboline | 70265-32-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 1-(3,4-dimethoxy-benzyl)-6-methoxy-2,3,4,9-tetrahydro-1H-β-carboline
• 英文别名: 1-(3,4-Dimethoxy-benzyl)-6-methoxy-1,2,3,4-tetrahydro-β-carbolin；2,3,4,9-Tetrahydro-1-((3,4-dimethoxyphenyl)methyl)-6-methoxy-1H-pyrido(3,4-b)indole；1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• CAS: 70265-32-6
• 化学式: C₂₁H₂₄N₂O₃
• 分子量: 352.433
• InChiKey: CSBAVYNEVHLVAF-UHFFFAOYSA-N

物化性质

• 沸点：
  542.5±45.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-4-(3,4-dimethoxybenzylidene)-2-methyl-5(4H)-oxazolone 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 1-(3,4-dimethoxy-benzyl)-6-methoxy-2,3,4,9-tetrahydro-1H-β-carboline
  参考文献：
  名称：

  Potent, Selective Tetrahydro-β-carboline Antagonists of the Serotonin 2B (5HT_2B) Contractile Receptor in the Rat Stomach Fundus

  摘要：

  A series of potent, selective 5HT(2B) receptor antagonists has been identified based upon yohimbine, with SAR studies resulting in a 1000-fold increase in 5HT(2B) receptor affinity relative to the starting structure (-log K(B)s > 10.0 have been obtained). These high-affinity tetrahydro-beta-carboline antagonists are able to discriminate among the 5HT(2) family of serotonin receptors, with members of the series showing selectivities of more than 100-fold versus both the 5HT(2A) and 5HT(2C) receptors based upon radioligand binding and functional assays. As the first compounds reported with such selectivity and enhanced receptor affinity, these tetrahydro-beta-carboline antagonists are useful tools for elucidating the role of serotonin acting at the 5HT(2B) receptor in normal and disease physiology.

  DOI：

  10.1021/jm960062t