(-)-O-N,N-(dimethylamino-ethyl)-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-(dimethylamino-ethyl)-cubebin
• 英文别名: (-)-O-(N,N-dimethylaminoethyl)-cubebin；2-[(3R,4R)-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-ZJWBFHOUSA-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 8.0h， 以71%的产率得到(-)-O-N,N-(dimethylamino-ethyl)-cubebin
  参考文献：
  名称：

  Analgesic and anti-inflammatory activities evaluation of (-)-O-acetyl, (-)-O-methyl, (-)-O-dimethylethylamine cubebin and their preparation from (-)-cubebin

  摘要：

  The anti-inflammatory and antinociceptive effects of the acetylated (2), methylated (3) and aminated (4) derivatives of cubebin (1), obtained by its reaction with acetic anhydride, methyl iodide and dimethylethylamine chloride, respectively, were investigated, using different animal models. The compound (2) was the most effective anti-inflammatory one in the carrageenin-induced paw edema in rats and was the only one which showed dose-response correlation for this assay with r = 0.993 and Y = 64.58x + 0.22. Besides, compounds (2) and (4) were more effective than cubebin in inhibiting acetic acid-induced writhing in mice, producing dose-response correlation with doses of 10, 20 and 30 mg/kg, respectively. Regarding the hot plate and the cell migration tests in rats, none of the four tested compounds showed activity. Overall, the results showed that the acetylation and amination of cubebin were efficient in enhancing its analgesic activity, as well as its anti-inflammatory activity.

  DOI：

  10.1016/j.farmac.2003.07.012

文献信息

• WO2007/9201
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2006/113981
  申请人：——

  公开号：——

  公开（公告）日：——
• PROCESS TO OBTAIN DIBENZYLBUTYROLACTONIC LIGNANS, PROCESS TO OBTAIN SYNTHETIC DERIVATIVES FROM LIGNANS BEARING ANTI-CHAGAS CHEMOPROPHYLACTIC AND THERAPEUTICAL ACTIVITIES
  申请人：SILVA Marcio Luis Andrade

  公开号：US20080090901A1

  公开（公告）日：2008-04-17

  The invention refers to a process to obtain lignans, especially to obtain cubebin and methylpluviatolide from leaves of Zanthoxylum naranjillo or Piper cubeba. It also refers to a process to obtain semi-synthetic derivatives of cubebin, especially dibenzylbutirloactonic lignans, such as: hinokinin, o-acetyl cubebin, o-methyl cubebin, 6,6′-dinitrohinokinin and o-dimethylethylamine cubebin and other derivatives which may be obtained, as well as to obtain methylpluviatolide derivatives, which are used to manufacture drugs to provide activity at least five times higher than observed for gentian violet and other compounds used heretofore for blood treatment and Chagas' disease prophylaxis.
• 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.
• US7317114B2
  申请人：——

  公开号：US7317114B2

  公开（公告）日：2008-01-08