3-Deoxyjesaconitine | 69787-27-5

• 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: 3-Deoxyjesaconitine
• 英文别名: deoxyjesaconitine；[(1S,2R,3R,4R,5R,6S,7S,8R,9R,13S,16S,17R,18R)-8-acetyloxy-11-ethyl-5,7-dihydroxy-6,16,18-trimethoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl] 4-methoxybenzoate
• CAS: 69787-27-5
• 化学式: C₃₅H₄₉NO₁₁
• 分子量: 659.774
• InChiKey: FCLBIQAIAWTNDU-YFOMEKLUSA-N

物化性质

• 沸点：
  711.9±60.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  jesaconitine 在 platinum(IV) oxide 氯化亚砜 、 氢气 作用下， 以 乙醇 为溶剂， 反应 4.5h， 生成 3-Deoxyjesaconitine
  参考文献：
  名称：

  Studies on the constituents of Aconitum species. XII. Syntheses of jasaconitine derivatives and their analgesic and toxic activities.

  摘要：

  研究人员还考察了3-O-乙酰基西沙康尼汀（2）、3-O-甲酰西沙康尼汀（3）和3-脱氧西沙康尼汀（6）的C3和C8取代基对西沙康尼汀诱导的镇痛和毒性所起的作用。3-O-Acetyljesaconitine (2)、3-O-anisoyljesaconitine (3)和 3-deoxyjesaconitine (6)显示出剂量依赖性镇痛作用，它们的化合物诱导镇痛和毒性的效力均低于 1。结果表明，1 的 C3 羟基功能参与了毒性而非镇痛的诱导。8-O-Linoleoyl-14-anisoylaconine (5)、8-O-甲基-14-anisoylaconine (7)、8-O-乙基-14-anisoylaconine (8)、14-anisoylaconine (4) 和 8-deoxy-14-anisoylaconine (9) 在诱导镇痛和毒性方面的活性低于 jesaconitine。7 的镇痛活性与 8 几乎相同，但 7 的毒性低于 8；9 的镇痛活性低于 4，但两种衍生物的毒性均不明显。这些事实表明，1 的 C8 功能对诱导镇痛和毒性非常重要，而且该功能在诱导镇痛和毒性方面的参与程度不同。随后，有人认为 1 的 C3 和 C8 取代物在诱导镇痛和毒性方面发挥了重要作用，而且这种参与镇痛和毒性的方式也不尽相同。

  DOI：

  10.1248/cpb.39.379

文献信息

• Mori, Takao; Bando, Hideo; Kanaiwa, Yoshio, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 8, p. 2884 - 2886
  作者：Mori, Takao、Bando, Hideo、Kanaiwa, Yoshio、Wada, Koji、Amiya, Takashi

  DOI：——

  日期：——
• Studies on the constituents of Aconitum species. XII. Syntheses of jasaconitine derivatives and their analgesic and toxic activities.
  作者：Takao MORI、Mitsuo MURAYAMA、Hideo BANDO、Norio KAWAHARA

  DOI：10.1248/cpb.39.379

  日期：——

  The role of the substituents at C3 and C8 of jesaconitine (1) on jesaconitine-induced analgesia and toxicity was examined. 3-O-Acetyljesaconitine (2), 3-O-anisoyljesaconitine (3), and 3-deoxyjesaconitine (6) showed dose-dependent analgesic action, and the potency of their compound-induced analgesia and toxicity was lower than those of 1. The most remarkable difference was found in the toxicity. The results indicate that the C3 hydroxy function of 1 participate in the induction of toxicity rather than of analgesia. 8-O-Linoleoyl-14-anisoylaconine (5), 8-O-methyl-14-anisoylaconine (7), 8-O-ethyl-14-anisoylaconine (8), 14-anisoylaconine (4) and 8-deoxy-14-anisoylaconine (9) showed lower activities than jesaconitine-induced analgesia and toxicity. The analgestic activity of 7 was almost the same as that of 8, but the toxicity of 7 was lower than that of 8. The analgesic activity of 9 was lower than that of 4, but the toxicities of both derivatives were not apparent. These facts indicate that the C8 function of 1 is important to the induction of analgesia and toxicity, and also that this function participates differently in the induction of the analgesia and toxicity. Subsequently, it was suggested that substitutents at C3 and C8 of 1 played important roles of the induction of the analgesia and toxicity, and that the modes of this participation were not the same in analgesia and toxicity.

  研究人员还考察了3-O-乙酰基西沙康尼汀（2）、3-O-甲酰西沙康尼汀（3）和3-脱氧西沙康尼汀（6）的C3和C8取代基对西沙康尼汀诱导的镇痛和毒性所起的作用。3-O-Acetyljesaconitine (2)、3-O-anisoyljesaconitine (3)和 3-deoxyjesaconitine (6)显示出剂量依赖性镇痛作用，它们的化合物诱导镇痛和毒性的效力均低于 1。结果表明，1 的 C3 羟基功能参与了毒性而非镇痛的诱导。8-O-Linoleoyl-14-anisoylaconine (5)、8-O-甲基-14-anisoylaconine (7)、8-O-乙基-14-anisoylaconine (8)、14-anisoylaconine (4) 和 8-deoxy-14-anisoylaconine (9) 在诱导镇痛和毒性方面的活性低于 jesaconitine。7 的镇痛活性与 8 几乎相同，但 7 的毒性低于 8；9 的镇痛活性低于 4，但两种衍生物的毒性均不明显。这些事实表明，1 的 C8 功能对诱导镇痛和毒性非常重要，而且该功能在诱导镇痛和毒性方面的参与程度不同。随后，有人认为 1 的 C3 和 C8 取代物在诱导镇痛和毒性方面发挥了重要作用，而且这种参与镇痛和毒性的方式也不尽相同。