9-n-hexyl-β-carboline-1-carboxaldehyde

• 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: 9-n-hexyl-β-carboline-1-carboxaldehyde
• 英文别名: 9-hexyl-β-carboline-1-carbaldehyde；9-Hexylpyrido[3,4-b]indole-1-carbaldehyde；9-hexylpyrido[3,4-b]indole-1-carbaldehyde
• 化学式: C₁₈H₂₀N₂O
• 分子量: 280.37
• InChiKey: MAHGJOLQKFZSFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-n-hexyl-β-carboline-1-carboxaldehyde 在 sodium cyanoborohydride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 N,N-bis[(9-hexyl-β-carboline-1-yl)methyl]hexane-1,6-diamine
  参考文献：
  名称：

  Synthesis and biological evaluation of novel alkyl diamine linked bivalent β-carbolines as angiogenesis inhibitors

  摘要：

  We have synthesized and evaluated a series of novel alkyl diamine linked bivalent beta-carbolines as potent angiogenesis inhibitors. The results demonstrated that most bivalent beta-carbolines exhibited significant antiproliferative effects against human umbilical vein cell lines EA.HY926. Compound 4m was found to be the most potent antiproliferative agent with IC50 value of 2.16 mu M against EA.HY926 cell lines. Mechanism investigations revealed that compound 4m could significantly inhibit EA.HY926 cells migration and tube formation in a dose-dependent manner. Moreover, compound 4m also showed obvious angiogenesis inhibitory effects in CAM assay, and the antiangiogenetic potency was more potent than the reference drug Endostar. The bivalent beta-carbolines might be served as candidates for the development of vascular targeting antitumor drugs. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.08.050
• 作为产物：
  描述：

  9-n-hexyl-1-methyl-β-carboline 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以61%的产率得到9-n-hexyl-β-carboline-1-carboxaldehyde
  参考文献：
  名称：

  Synthesis and biological evaluation of novel alkyl diamine linked bivalent β-carbolines as angiogenesis inhibitors

  摘要：

  We have synthesized and evaluated a series of novel alkyl diamine linked bivalent beta-carbolines as potent angiogenesis inhibitors. The results demonstrated that most bivalent beta-carbolines exhibited significant antiproliferative effects against human umbilical vein cell lines EA.HY926. Compound 4m was found to be the most potent antiproliferative agent with IC50 value of 2.16 mu M against EA.HY926 cell lines. Mechanism investigations revealed that compound 4m could significantly inhibit EA.HY926 cells migration and tube formation in a dose-dependent manner. Moreover, compound 4m also showed obvious angiogenesis inhibitory effects in CAM assay, and the antiangiogenetic potency was more potent than the reference drug Endostar. The bivalent beta-carbolines might be served as candidates for the development of vascular targeting antitumor drugs. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.08.050