7-methoxy-1,2,3,4-tetrahydro-β-carboline | 91566-22-2

• 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: 7-methoxy-1,2,3,4-tetrahydro-β-carboline
• 英文别名: 7-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• CAS: 91566-22-2
• 化学式: C₁₂H₁₄N₂O
• 分子量: 202.256
• InChiKey: SCIRNASYBOGBOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-methoxy-1,2,3,4-tetrahydro-β-carboline 在 palladium 10% on activated carbon 作用下， 以 吡啶 、 xylene 为溶剂， 反应 5.0h， 生成 7-甲氧基-9h-吡啶并[3,4-b]吲哚
  参考文献：
  名称：

  Substituted beta-carbolines

  摘要：

  式I的化合物适用于生产用于预防和治疗在其过程中涉及IκB激酶活性增加的疾病的药物。

  公开号：

  EP1209158A1
• 作为产物：
  描述：

  在 sodium carbonate 作用下， 以 水 为溶剂， 生成 7-methoxy-1,2,3,4-tetrahydro-β-carboline
  参考文献：
  名称：

  Substituted beta-carbolines

  摘要：

  式I的化合物适用于生产用于预防和治疗在其过程中涉及IκB激酶活性增加的疾病的药物。

  公开号：

  EP1209158A1

文献信息

• Structure–activity relationship study of beta-carboline derivatives as haspin kinase inhibitors
  作者：Gregory D. Cuny、Natalia P. Ulyanova、Debasis Patnaik、Ji-Feng Liu、Xiangjie Lin、Ken Auerbach、Soumya S. Ray、Jun Xian、Marcie A. Glicksman、Ross L. Stein、Jonathan M.G. Higgins

  DOI：10.1016/j.bmcl.2012.01.028

  日期：2012.3

  Haspin is a serine/threonine kinase that phosphorylates Thr-3 of histone H3 in mitosis that has emerged as a possible cancer therapeutic target. High throughput screening of approximately 140,000 compounds identified the beta-carbolines harmine and harmol as moderately potent haspin kinase inhibitors. Based on information obtained from a structure-activity relationship study previously conducted for an acridine series of haspin inhibitors in conjunction with in silico docking using a recently disclosed crystal structure of the kinase, harmine analogs were designed that resulted in significantly increased haspin kinase inhibitory potency. The harmine derivatives also demonstrated less activity towards DYRK2 compared to the acridine series. In vitro mouse liver microsome stability and kinase profiling of a representative member of the harmine series (42, LDN-211898) are also presented. (C) 2012 Elsevier Ltd. All rights reserved.
• Pouilhes, Annie; Langlois, Yves, Heterocycles, 1985, vol. 23, # 4, p. 935 - 938
  作者：Pouilhes, Annie、Langlois, Yves

  DOI：——

  日期：——
• Structure-activity relationship for a series of 2-substituted 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indoles: Potent subtype-selective inhibitors of (NMDA) receptors
  作者：Amir P. Tamiz、Edward R. Whittemore、Richard M. Woodward、Ravindra B. Upasani、John F.W. Keana

  DOI：10.1016/s0960-894x(99)00248-6

  日期：1999.6

  series of 2-substituted 1,2,3,4-tetrahydro-9H-pyrido[3,4-b] indoles was synthesized as potential antagonists for the NR1A/2B subtype of N-methyl-D-aspartate (NMDA) receptors. Assayed by electrical recording under steady-state conditions, 7-hydroxy-2-(4-phenylbutyl)-1,2,3,4-tetrahydropyrido-[3,4-b]indole (30) was the most potent compound in the series having an IC50 value of 50 nM at the MR1A/2B receptors. (C) 1999 Elsevier Science Ltd. All rights reserved.
• POUILHES, A.;LANGLOIS, Y., HETEROCYCLES, 1985, 23, N 4, 935-938
  作者：POUILHES, A.、LANGLOIS, Y.

  DOI：——

  日期：——