2-[3-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)propyl]isoindole-1,3-dione

• 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-[3-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)propyl]isoindole-1,3-dione
• 英文别名: 2-[3-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)propyl]isoindoline-1,3-dione；2-[3-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)propyl]isoindole-1,3-dione
• 化学式: C₂₂H₂₁N₃O₂
• 分子量: 359.428
• InChiKey: AEHPJWOORSYVKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[3-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)propyl]isoindole-1,3-dione 在 2-氯-1-甲基吡啶碘化物 、 一水合肼 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 96.08h， 生成 tert-butyl (3-(9H-pyrido[3,4-b]indol-1-yl)propylamino)(tert-butoxycarbonylamino)methylenecarbamate
  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：

  4-(1,3-二氧代异吲哚啉-2-基)丁醛 、 色胺 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到2-[3-(2,3,4,9-tetrahydro-1H-β-carbolin-1-yl)propyl]isoindole-1,3-dione
  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

文献信息

• Antimalarial β-Carbolines from the New Zealand Ascidian <i>Pseudodistoma opacum</i>
  作者：Susanna T. S. Chan、A. Norrie Pearce、Michael J. Page、Marcel Kaiser、Brent R. Copp

  DOI：10.1021/np200509g

  日期：2011.9.23

  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.