2-ethyl-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole | 3584-36-9

• 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: 2-ethyl-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• 英文别名: 2-ethyl-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline；2-ethyl-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline；1-Phenyl-2-ethyl-1,2,3,4-tetrahydro-β-carbolin；2-Ethyl-1-phenyl-1,3,4,9-tetrahydropyrido[3,4-b]indole
• CAS: 3584-36-9
• 化学式: C₁₉H₂₀N₂
• 分子量: 276.381
• InChiKey: IREGPWOWWJSLQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  19.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-ethyl-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 365.83h， 生成 methyl 3-ethyl-7-[(4-methylphenyl)sulfonyl]-6-phenyl-2,3,6,7-tetrahydro-1H-azocino[5,4-b]indole-5-carboxylate
  参考文献：
  名称：

  Synthesis of 6-aryl-Substituted Azocino-[5,4-b]indoles from 1-aryl-Substituted 2-Ethyltetrahydro-β-Carbolines

  摘要：

  We optimized the reaction of tetrahydropyridine ring expansion in 1-aryl-substituted tetrahydro-beta-carbolines by the action of activated alkynes and achieved higher than 70% yields of the target indoloazocines. The substituents in the 1-aryl ring and at the indole nitrogen atom were shown to affect the rate and selectivity of this transformation.

  DOI：

  10.1007/s10593-014-1518-z
• 作为产物：
  描述：

  苯甲醛 在 silica gel 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 2-ethyl-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
  参考文献：
  名称：

  Discovery of 3,3′-pyrrolidinyl-spirooxindoles as cardioprotectant prohibitin ligands

  摘要：

  The scaffold proteins prohibitins-1 and 2 (PHB1/2) play many important roles in coordinating many cell signaling pathways and represent emerging targets in cardiology and oncology. We previously reported that a family of natural products derivatives, flavaglines, binds to PHB1/2 to exert cardioprotectant and anti-cancer effects. However, flavaglines also target the initiation factor of translation elF4A, which doesn't contribute to cardioprotection and may even induce some adverse effects. Herein, we report the development of a convenient and robust synthesis of the new PHB2 ligand 2'-phenylpyrrolidinyl-spirooxindole, and its analogues. We discovered that these compounds displays cardioprotective effect against doxorubicin mediated cardiotoxicity and uncovered the structural requirement for this activity. We identified in particular some analogues that are more cardioprotectant than flavaglines. Pull-down experiments demonstrated that these compounds bind not only to PHB2 but also PHB1. These novel PHB ligands may provide the basis for the development of new drugs candidates to protect the heart against the adverse effects of anticancer treatments. (C) 2019 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.111859