lappaconitine | 32854-75-4

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: lappaconitine
• 英文别名: (+)-Lappaconitine；[(1S,2S,3S,4S,5R,6S,8S,9S,10R,13S,16S,17S)-11-ethyl-3,8-dihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-13-yl] 2-acetamidobenzoate
• CAS: 32854-75-4
• 化学式: C₃₂H₄₄N₂O₈
• 分子量: 584.71
• InChiKey: NWBWCXBPKTTZNQ-QOQRDJBUSA-N

物化性质

• 熔点：
  217-218°
• 比旋光度：
  D18 +27° (chloroform)
• 沸点：
  641.72°C (rough estimate)
• 密度：
  1.1897 (rough estimate)
• 溶解度：
  氯仿：30mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  127
• 氢给体数：
  3
• 氢受体数：
  9

制备方法与用途

生物活性高乌甲素（Lappaconitine）是从高乌头中分离出的一种天然产物，具有显著的镇痛作用。

化学性质上，高乌甲素为白色针状结晶，可溶于甲醇、乙醇及DMSO等有机溶剂。它来源于毛茛科植物如高乌头根、川乌和附子。

用途方面，高乌甲素不仅具有抗炎、消肿、解热、局麻和镇痛的效果，还用于含量测定、鉴定以及药理实验等。

具体药理药效包括强效镇痛、降温消热、抗炎消热及增强免疫力等功能。其应用范围广泛，主要用于治疗癌痛、头痛、牙痛、肩臂痛、颈椎痛、腰痛、结石痛、外伤疼痛、风湿痛、胃肠溃疡疼痛、神经性疼痛、坐骨神经痛以及由妇炎症引发的各种疼痛等。此外，它在术后镇痛方面也有显著效果。

反应信息

• 作为反应物：
  描述：

  lappaconitine 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 7.0h， 生成 20-ethyl-1α,16β-dimethoxyaconitane-4,8,9,14α-tetrol
  参考文献：
  名称：

  Study of alkaloids of the Siberian and Altai flora. 11. Synthesis of new lappaconitine derivatives

  摘要：

  A convenient procedure was developed for the preparation of N-deacetyllappaconitine by acid hydrolysis of lappaconitine. The crystal and molecular structures of by-products of acid hydrolysis of lappaconitine, viz., 14- and 16-demetliyl-N-deacetyllappaconitines, were established by X-ray diffraction analysis. Azocoupling of diazonium chlorides that were prepared from lappaconitine N-deacetylation products with beta-naplithol afforded the corresponding 1,2-naphthoquinone 1-hydrazones.

  DOI：

  10.1023/b:rucb.0000012376.73950.84
• 作为产物：
  描述：

  4β-(2-acetylaminobenzoyloxy)-1α,14α,16β-trimethoxyaconitane-8,9-diol 、 溴乙烷 反应 96.0h， 以70%的产率得到lappaconitine
  参考文献：
  名称：

  Study of alkaloids of the Siberian and Altai flora. 10. Synthesis of N(20)-deethyllappaconitine derivatives

  摘要：

  Efficient procedures were developed for N-deethylation of lappaconitine to give N(20)-deethyllappaconitine. Alkyl derivatives of N(20)-deethyllappaconitine, including labeled lappaconitine, and N(20)-acetoxy-N(20)-deethyllappaconitine were prepared for the first time. The assignments of the signals for the carbon atoms in the C-13 NMR spectra of lappaconitine and related lappaconine were refined using C-13-C-13 2D INADEQUATE and 2D C-13-H-1 correlation experiments.

  DOI：

  10.1023/b:rucb.0000012375.59390.38

文献信息

• Study of alkaloids of the Siberian and Altai flora
  作者：S. A. Osadchii、E. E. Shul’ts、E. V. Polukhina、M. M. Shakirov、G. A. Tolstikov

  DOI：10.1007/s11172-006-0380-2

  日期：2006.6

  Lappaconitine and N-deacetyllappaconitine derivatives containing bromine and iodine atoms in the aromatic moiety were synthesized. The Heck cross-coupling of these halides with ethyl acrylate or 2-methyl-5-vinylpyridine afforded new olefinated lappaconitine derivatives.

  合成了含有溴和碘原子的芳香环拉帕克尼丁（Lappaconitine）和去乙酰拉帕克尼丁（N-deacetyllappaconitine）衍生物。这些卤化物与乙基丙烯酸酯或2-甲基-5-乙烯基吡啶进行Heck交叉偶联反应，得到了新的 olefinated拉帕克尼丁衍生物。
• Molecular structure of 5′-bromolappaconitine
  作者：V. E. Romanov、Yu. V. Gatilov、E. E. Shul′ts、G. A. Tolstikov

  DOI：10.1007/s10600-009-9186-4

  日期：2008.11

  The structure of 5′-bromolappaconitine that was synthesized by an alternate method was solved by XSA.

  通过另一种方法合成的5′-溴拉帕科宁的结构通过XSA解析。
• Synthesis of acetylene derivatives of lappaconitine
  作者：S. F. Vasilevskii、S. A. Osadchii、E. E. Shults、E. V. Polukhina、A. A. Stepanov、G. A. Tolstikov

  DOI：10.1134/s0012500807080010

  日期：2007.8
• Design, synthesis and anti-inflammatory activity of diterpenoid alkaloids and non-steroidal anti-inflammatory drug hybrids based on molecular hybridization strategy
  作者：Ming-Hao Guo、Peng Wen、Yao Xiao、Wan-Sheng Ji、Xian-Li Zhou、Feng Gao、Lian-Hai Shan

  DOI：10.1016/j.fitote.2023.105536

  日期：2023.7
• Study of alkaloids of the Siberian and Altai flora. 10. Synthesis of N(20)-deethyllappaconitine derivatives
  作者：N. A. Pankrushina、I. A. Nikitina、N. V. Anferova、S. A. Osadchii、M. M. Shakirov、E. E. Shults、G. A. Tolstikov

  DOI：10.1023/b:rucb.0000012375.59390.38

  日期：2003.11

  Efficient procedures were developed for N-deethylation of lappaconitine to give N(20)-deethyllappaconitine. Alkyl derivatives of N(20)-deethyllappaconitine, including labeled lappaconitine, and N(20)-acetoxy-N(20)-deethyllappaconitine were prepared for the first time. The assignments of the signals for the carbon atoms in the C-13 NMR spectra of lappaconitine and related lappaconine were refined using C-13-C-13 2D INADEQUATE and 2D C-13-H-1 correlation experiments.