(-)-O-(N,N-dimethylaminoethyl)-cubebin

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (-)-O-(N,N-dimethylaminoethyl)-cubebin
• 英文别名: 2-[(3S,4S)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-yl]oxy-N,N-dimethylethanamine
• 化学式: C₂₄H₂₉NO₆
• 分子量: 427.497
• InChiKey: UBTZIBNJIZJWIK-WEAPTXNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (-)-cubebin 、 2-氯-N,N-二甲基乙胺 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以71%的产率得到(-)-O-(N,N-dimethylaminoethyl)-cubebin
  参考文献：
  名称：

  Trypanocidal activity of (−)-cubebin derivatives against free amastigote forms of Trypanosoma cruzi

  摘要：

  Five (-)-cubebin derivative compounds, (-)-O-acetyl cubebin (3), (-)-O-benzyl cubebin (4), (-)-O-(N,N-dimethylaminoethyl)-cubebin (5), (-)-hinokinin (6) and (-)-6,6'-dinitrohinokinin (7), previously synthesised by our research group, were evaluated on in vitro assay against free amastigote forms of Trypanosoina cruzi, the asogic agent of Chagas' disease. It was observed that 6 was the most active compound (IC50 = 0.7 muM), and that 4 and 5 displayed moderate activity against the parasite, giving IC50 values of 5.7 and 4.7 muM, respectively. In contrast, it was observed that compound 3 was inactive and that 7 displayed low activity with IC50 values of congruent to1.5 x 10(4) and 95.3 muM, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.10.079

文献信息

• Process To Obtain Dibenzylbutyrolactonic, Tetrahydrofuranic Lignans And Their Synthetic And Semi-Synthetic Derivatives, Their Analgesic And Anti-Inflammatory Activities, Topical And/Or Systemic Formulations Containing Said Lignans And Their Respective Therapeutic Method
  申请人：Silva Marcio Luis Andrade e

  公开号：US20080214661A1

  公开（公告）日：2008-09-04

  A process to obtain dibenzylbutyrolactonic lignans from (-)-cubebin, isolated from a Piperaceae, especially Piper cubeba, and from (-)-methylpluviatolide, isolated from a Rutacea, especially Zanthoxylum naranjillo; their synthetic and semi-synthetic derivatives and tetrahydrofuranic lignans, such as galgravin and veragensin, isolated from Nectandra megapotamica, as well as the analgesic and anti-inflammatory activities of said lignans, and the topical and/or systemic formulations. Also presented is a therapeutic method using topic and/or systemic formulations based on said lignans for the treatment of inflammation and/or pain. Further, a process to obtain synthetic and semi-synthetic derivatives of (-)-cubebin, such as: (-)—O-acetyl cubebin; (-)—O-methyl cubebin; (-)—O—(N,N-dimethylamino-ethyl)-cubebin; (-)-hinokinin; (-)- 6,6 ′-dinitroinokinin; (-)—O-benzyl cubebin; (-)- 6,6 ′-diaminohinokinin and other synthetic derivatives which may be obtained, and synthetic and semi-synthetic derivatives of (-)-methylpluviatolide, such as (-)- 6,6 ′-dinitromethylpluviatolide and (-)- 6,6 ′-diaminomethylpluviatolide, to be used in the manufacture of medicine that has analgesic and anti-inflammatory activity is presented.
• Trypanocidal activity of (−)-cubebin derivatives against free amastigote forms of Trypanosoma cruzi
  作者：Vanessa A. de Souza、Rosangela da Silva、Ana C. Pereira、Vanessa de A. Royo、Juliana Saraiva、Marisa Montanheiro、Gustavo H.B. de Souza、Ademar A. da Silva Filho、Marcella D. Grando、Paulo M. Donate、Jairo K. Bastos、Sérgio Albuquerque、Márcio L.A. e Silva

  DOI：10.1016/j.bmcl.2004.10.079

  日期：2005.1

  Five (-)-cubebin derivative compounds, (-)-O-acetyl cubebin (3), (-)-O-benzyl cubebin (4), (-)-O-(N,N-dimethylaminoethyl)-cubebin (5), (-)-hinokinin (6) and (-)-6,6'-dinitrohinokinin (7), previously synthesised by our research group, were evaluated on in vitro assay against free amastigote forms of Trypanosoina cruzi, the asogic agent of Chagas' disease. It was observed that 6 was the most active compound (IC50 = 0.7 muM), and that 4 and 5 displayed moderate activity against the parasite, giving IC50 values of 5.7 and 4.7 muM, respectively. In contrast, it was observed that compound 3 was inactive and that 7 displayed low activity with IC50 values of congruent to1.5 x 10(4) and 95.3 muM, respectively. (C) 2004 Elsevier Ltd. All rights reserved.