(RS)-1-(4-phthalimidobutyl)-1,2,3,4-tetrahydro-β-carboline | 163980-67-4

• 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: (RS)-1-(4-phthalimidobutyl)-1,2,3,4-tetrahydro-β-carboline
• 英文别名: 2-[4-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)butyl]isoindole-1,3-dione
• CAS: 163980-67-4
• 化学式: C₂₃H₂₃N₃O₂
• 分子量: 373.455
• InChiKey: WBZAFUXBJDTNHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  (RS)-1-(4-phthalimidobutyl)-1,2,3,4-tetrahydro-β-carboline 在 2-氯-1-甲基吡啶碘化物 、 一水合肼 、 三乙胺 、 三氟乙酸 、 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 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.62h， 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
• 作为产物：
  描述：

  1-(4-phthalimidobutyl)-3,4-dihydro-β-carboline 在 镍 乙醇 、 氨 、 氢气 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以71%的产率得到(RS)-1-(4-phthalimidobutyl)-1,2,3,4-tetrahydro-β-carboline
  参考文献：
  名称：

  (RS) - 和 (S) - (-) - Nazlinin 和 (RS) - 和 (+) - 6-azacyclodeca [5,4-b] indol-1-amines 的合成

  摘要：

  (RS)-1-(4-氨基丁基)-1,2,3,4-四氢-β-咔啉((RS)-1)以两种不同的方式合成。(S) - (-) - 1 的制备通过 ⩾ 95% ee 的不对称还原和 (S) - (+) - 3 的合成进行。从该化合物还以高对映选择性制备了 (+) - 6 - azacyclodeca [5,4 - b] 吲哚 - 1 - 胺 ((+) - 2)。

  DOI：

  10.1002/ardp.19953280415

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.
• Syntheses of (RS)- and (S)-(−)-Nazlinin and (RS)- and (+)-6-Azacyclodeca[5,4-b]indol-1-amine
  作者：Siavosh Mahboobi、Wolfgang Wagner、Thomas Burgemeister

  DOI：10.1002/ardp.19953280415

  日期：——

  (RS)‐1‐(4‐Aminobutyl)‐1,2,3,4‐tetrahydro‐β‐carboline ((RS)‐1) was synthesized in two different ways. The preparation of (S)‐(−)‐1 was performed both by asymmetric reduction with ⩾ 95% ee and by synthesis from (S)‐(+)‐3. From this compound also (+)‐6‐azacyclodeca[5,4‐b]indol‐1‐amine ((+)‐2) was prepared with high enantioselectivity.

  (RS)-1-(4-氨基丁基)-1,2,3,4-四氢-β-咔啉((RS)-1)以两种不同的方式合成。(S) - (-) - 1 的制备通过 ⩾ 95% ee 的不对称还原和 (S) - (+) - 3 的合成进行。从该化合物还以高对映选择性制备了 (+) - 6 - azacyclodeca [5,4 - b] 吲哚 - 1 - 胺 ((+) - 2)。