(6-methoxy-9H-β-carbolin-1-yl)(4-methoxyphenyl)methanone

• 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: (6-methoxy-9H-β-carbolin-1-yl)(4-methoxyphenyl)methanone
• 英文别名: (4-methoxyphenyl)-(6-methoxy-9H-pyrido[3,4-b]indol-1-yl)methanone
• 化学式: C₂₀H₁₆N₂O₃
• 分子量: 332.359
• InChiKey: AUXWNNNZBPKLSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  64.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6-methoxy-9H-β-carbolin-1-yl)(4-methoxyphenyl)methanone 在 氢溴酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 24.0h， 以30%的产率得到linderaggrine A
  参考文献：
  名称：

  Synthesis and structural characterization of an anti-inflammatory principle purified from Lindera aggregata

  摘要：

  Linderaggrine A (1) was characterized from the roots of Lindera aggregata and its chemical structure was established by the spectral analysis and chemical transformation. The chemical preparation of 1 and its isomer 2 provide unambiguous evidences for the structural determination of the naturally isolated compound. In addition, the inhibition of superoxide anion generation and elastase release by human neutrophils in response to FMLP/cytochalasin B of these synthetic products had been examined and among the tested compounds, linderaggrine A (1) displayed significant potential against the superoxide anion generation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.126
• 作为产物：
  描述：

  5-甲氧基色胺 、 2-(4-甲氧基苯基)-2-氧代乙醛 在 盐酸 、 manganese(IV) oxide 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 96.0h， 以38%的产率得到(6-methoxy-9H-β-carbolin-1-yl)(4-methoxyphenyl)methanone
  参考文献：
  名称：

  Synthesis and structural characterization of an anti-inflammatory principle purified from Lindera aggregata

  摘要：

  Linderaggrine A (1) was characterized from the roots of Lindera aggregata and its chemical structure was established by the spectral analysis and chemical transformation. The chemical preparation of 1 and its isomer 2 provide unambiguous evidences for the structural determination of the naturally isolated compound. In addition, the inhibition of superoxide anion generation and elastase release by human neutrophils in response to FMLP/cytochalasin B of these synthetic products had been examined and among the tested compounds, linderaggrine A (1) displayed significant potential against the superoxide anion generation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.126

文献信息

• A versatile route to the synthesis of 1-substituted β-carbolines by a single step Pictet–Spengler cyclization
  作者：Mei-Lin Yang、Ping-Chung Kuo、Amooru G. Damu、Ren-Jie Chang、Wen-Fei Chiou、Tian-Shung Wu

  DOI：10.1016/j.tet.2006.08.081

  日期：2006.11

  A one-step conversion of L-tryptophan and activated aldehydes (1,2-dicarbonyl compounds) directly to 1-substituted beta-carbolines without formation of the tetrahydro derivatives under modified Pictet-Spengler conditions was described. Moreover, a practical application for the synthesis of a natural 1-substituted beta-carboline, luzongerine A, isolated from Illigera luzonensis was also successfully carried out utilizing this protocol. The effects of synthetic compounds 11 and 11a on nitric oxide (NO) production in LPS/IFN-gamma stimulated RAW 264.7 macrophage cells were evaluated in vitro. They displayed significant dose-dependent inhibition of inducible nitric oxide synthase (iNOS). (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and structural characterization of an anti-inflammatory principle purified from Lindera aggregata
  作者：Ping-Chung Kuo、Yue-Chiun Li、Tsong-Long Hwang、Guo-Hao Ma、Mei-Lin Yang、E-Jian Lee、Tian-Shung Wu

  DOI：10.1016/j.tetlet.2013.10.126

  日期：2014.1

  Linderaggrine A (1) was characterized from the roots of Lindera aggregata and its chemical structure was established by the spectral analysis and chemical transformation. The chemical preparation of 1 and its isomer 2 provide unambiguous evidences for the structural determination of the naturally isolated compound. In addition, the inhibition of superoxide anion generation and elastase release by human neutrophils in response to FMLP/cytochalasin B of these synthetic products had been examined and among the tested compounds, linderaggrine A (1) displayed significant potential against the superoxide anion generation. (C) 2013 Elsevier Ltd. All rights reserved.