N-1',N-5-dimethyl-yuehchukene | 122284-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-1',N-5-dimethyl-yuehchukene
• 英文别名: N,N'-dimethylyuehchukene
• CAS: 122284-47-3
• 化学式: C₂₈H₃₀N₂
• 分子量: 394.56
• InChiKey: WITPDHKNRLNFCA-RFLWCCGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.89
• 重原子数：
  30.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  9.86
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  phenyl benzyl[3-methyl-1-(1-methyl-1H-indol-3-yl)but-2-en-1-yl]carbamate 在 三甲基氯硅烷 作用下， 以 乙二醇二甲醚 为溶剂， 反应 16.0h， 以35%的产率得到N-1',N-5-dimethyl-yuehchukene
  参考文献：
  名称：

  SHORT APPROACH TO BISINDOLE ALKALOID, YUEHCHUKENE, USING 2-INDOLYLCYANOCUPRATE

  摘要：

  A short total synthesis of a bisindole alkaloid, yuechukene, was achieved through the dimerization of beta-dehydroprenylindole generated in situ from 1-(indol-3-yl)-3-methylbut-2-en-1-amine.

  DOI：

  10.3987/com-12-s(n)49

文献信息

• Structure function relationship study of yuehchukene. I. Anti-implantation and estrogenic activities of substituted yuehchukene derivatives
  作者：WL Chan、DD Ho、CP Lau、KH Wat、YC Kong、KF Cheng、TT Wong、TY Chan

  DOI：10.1016/0223-5234(91)90099-9

  日期：1991.6

  (+/-)-Yuehchukene (YCK) is a novel bis-indole alkaloid with potent anti-implantation activity in rats. The present paper reports the activity of YCK derivatives by substitution on the parent compound. Substitutions on the indole nitrogens or on 2- and 5'- positions of the indole moiety abolished activity. N-1'-methylation of the free indole only permitted a 30% residual activity. Saturation of the C-9-C-10 cyclohexenyl double bond did not affect activity at all. Hydroxylation, whether on the C-9-C-10 double bond, or at C2 or C5, rendered the hydroxylated derivatives inactive. This suggests that the active metabolite in anti-implantation was probably not a hydroxylated derivative carrying estrogenic activity.

  (±)-Yuehchukene (YCK) 是一种具有强效抗着床活性的新型双吲哚生物碱。本文报告了YCK衍生物通过在母体化合物上进行的取代反应的活性。在吲哚的氮原子或吲哚基团的2-位和5'-位进行取代反应会使活性消失。仅对游离吲哚进行N-1'-甲基化处理，活性仅保持30%。饱和C-9-C-10环己烯基双键对活性没有任何影响。无论是对C-9-C-10双键、还是在C2或C5处进行羟基化处理，所得的羟基化衍生物均失去活性。这表明在抗着床活性的代谢产物中，很可能并非是具有雌激素活性的羟基化衍生物。