1-(4-(9H-pyrido[3,4-b]indol-1-yl)butyl)guanidine | 1329087-07-1

• 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-(4-(9H-pyrido[3,4-b]indol-1-yl)butyl)guanidine
• 英文别名: 2-[4-(9H-pyrido[3,4-b]indol-1-yl)butyl]guanidine
• CAS: 1329087-07-1
• 化学式: C₁₆H₁₉N₅
• 分子量: 281.36
• InChiKey: DJUXGCPKJDHXCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  93.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-(9H-pyrido[3,4-b]indol-1-yl)butyl)guanidine 、 三氟乙酸 以 甲醇 为溶剂， 以0.008 g的产率得到1-(4-(9H-pyrido[3,4-b]indol-1-yl)butyl)guanidine ditrifluoroacetic acid salt
  参考文献：
  名称：

  Antimalarial β-Carbolines from the New Zealand Ascidian Pseudodistoma opacum

  摘要：

  One tetrahydro-beta-carboline, (-)-7-bromohomotrypargine (1), and three alkylguanidine-substituted beta-carbolines, opacalines A, B, and C (2-4), have been isolated from the New Zealand ascidian Pseudodistoma opacum. The structures of the metabolites were determined by analysis of mass spectrometric and 2D NMR spectroscopic data. Natural products 2 and 3, synthetic debromo analogues 8 and 9, and intermediate 16 exhibited moderate antimalarial activity toward a chloroquine-resistant strain of Plasmodium falciparum, with an IC50 range of 2.5-14 mu M. The biosynthesis of 1-4 is proposed to proceed via a Pictet-Spengler condensation of 6-bromotryptamine and the alpha-keto acid transamination product of either arginine or homoarginine. Cell separation and H-1 NMR analysis of P. opacum identified tetrahydro-beta-carboline 1 to be principally located in the zooids, while fully aromatized analogues 2-4 were localized to the test.

  DOI：

  10.1021/np200509g
• 作为产物：
  描述：

  1-(4-butylamino)-β-carboline 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.5h， 生成 1-(4-(9H-pyrido[3,4-b]indol-1-yl)butyl)guanidine
  参考文献：
  名称：

  Antimalarial β-Carbolines from the New Zealand Ascidian Pseudodistoma opacum

  摘要：

  One tetrahydro-beta-carboline, (-)-7-bromohomotrypargine (1), and three alkylguanidine-substituted beta-carbolines, opacalines A, B, and C (2-4), have been isolated from the New Zealand ascidian Pseudodistoma opacum. The structures of the metabolites were determined by analysis of mass spectrometric and 2D NMR spectroscopic data. Natural products 2 and 3, synthetic debromo analogues 8 and 9, and intermediate 16 exhibited moderate antimalarial activity toward a chloroquine-resistant strain of Plasmodium falciparum, with an IC50 range of 2.5-14 mu M. The biosynthesis of 1-4 is proposed to proceed via a Pictet-Spengler condensation of 6-bromotryptamine and the alpha-keto acid transamination product of either arginine or homoarginine. Cell separation and H-1 NMR analysis of P. opacum identified tetrahydro-beta-carboline 1 to be principally located in the zooids, while fully aromatized analogues 2-4 were localized to the test.

  DOI：

  10.1021/np200509g