1-Cyclohexylmethyl-6-methyl-2,3,4,9-tetrahydro-1H-β-carboline

• 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-Cyclohexylmethyl-6-methyl-2,3,4,9-tetrahydro-1H-β-carboline
• 英文别名: 1-(cyclohexylmethyl)-6-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• 化学式: C₁₉H₂₆N₂
• 分子量: 282.429
• InChiKey: ODVMSLIYOUYHRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  D(+)-10-樟脑磺酸 、 1-Cyclohexylmethyl-6-methyl-2,3,4,9-tetrahydro-1H-β-carboline 以 异丙醇 为溶剂， 以46%的产率得到
  参考文献：
  名称：

  Efficient Fast Screening Methodology for Optical Resolution Agents:  Solvent Effects Are Used To Affect the Efficiency of the Resolution Process

  摘要：

  An efficient and fast screening methodology for optical resolution agents through the classical crystallization of the corresponding diastereomeric salts is described. In this contribution, we demonstrate that the determination of the eutectic composition by chiral analysis of the corresponding mother liquor (ML) obtained under appropriate experimental conditions provides us with a very fast screening methodology. We also demonstrate that solvent can have a profound effect not only on the efficiency of the resolution process by modifying the eutectic composition but also on the ease of crystallization.

  DOI：

  10.1021/op0499627
• 作为产物：
  描述：

  在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 1-Cyclohexylmethyl-6-methyl-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