(1R,9R,10R)-16-methyl-14-prop-2-enoyl-6,14-diazatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,16-trien-5-one | 845717-73-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: (1R,9R,10R)-16-methyl-14-prop-2-enoyl-6,14-diazatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,16-trien-5-one
• CAS: 845717-73-9
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: KLEPJDCEBXWTMF-IQUTYRLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-二甲基-1,6-己二胺 、 (1R,9R,10R)-16-methyl-14-prop-2-enoyl-6,14-diazatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,16-trien-5-one 在 silica gel 作用下， 以 乙腈 为溶剂， 生成 N,N'-dimethyl-N,N'-bis[2-(1-oxo-8,15-didehydrolycodinocarbonyl)ethyl]-1,6-hexanediamine
  参考文献：
  名称：

  Bis-huperzine B:  Highly Potent and Selective Acetylcholinesterase Inhibitors

  摘要：

  By targeting dual active sites of AChE, a series of bis-huperzine B analogues with various lengths of the tether were designed, synthesized, and tested for their inhibition and selectivity. The most potent bis-huperzine B (5g) exhibited 3900-fold increase in AChE inhibition and 930-fold greater in selectivity for AChE vs BuChE than its parent huperzine B.

  DOI：

  10.1021/jm0496178
• 作为产物：
  描述：

  石杉碱乙 、 丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以95%的产率得到(1R,9R,10R)-16-methyl-14-prop-2-enoyl-6,14-diazatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,16-trien-5-one
  参考文献：
  名称：

  Bis-huperzine B:  Highly Potent and Selective Acetylcholinesterase Inhibitors

  摘要：

  By targeting dual active sites of AChE, a series of bis-huperzine B analogues with various lengths of the tether were designed, synthesized, and tested for their inhibition and selectivity. The most potent bis-huperzine B (5g) exhibited 3900-fold increase in AChE inhibition and 930-fold greater in selectivity for AChE vs BuChE than its parent huperzine B.

  DOI：

  10.1021/jm0496178

文献信息

• Bis-huperzine B:  Highly Potent and Selective Acetylcholinesterase Inhibitors
  作者：Song Feng、Zhifei Wang、Xuchang He、Suxin Zheng、Yu Xia、Hualiang Jiang、Xican Tang、Donglu Bai

  DOI：10.1021/jm0496178

  日期：2005.2.1

  By targeting dual active sites of AChE, a series of bis-huperzine B analogues with various lengths of the tether were designed, synthesized, and tested for their inhibition and selectivity. The most potent bis-huperzine B (5g) exhibited 3900-fold increase in AChE inhibition and 930-fold greater in selectivity for AChE vs BuChE than its parent huperzine B.
• Study on dual-site inhibitors of acetylcholinesterase: Highly potent derivatives of bis- and bifunctional huperzine B
  作者：Xu-Chang He、Song Feng、Zhi-Fei Wang、Yufang Shi、Suxin Zheng、Yu Xia、Hualiang Jiang、Xi-can Tang、Donglu Bai

  DOI：10.1016/j.bmc.2006.11.009

  日期：2007.2.1

  Natural (-)-huperzine B (HupB), isolated from Chinese medicinal herb, displayed moderate inhibitory activity of acetylcholinesterase (AChE). Based on the active dual-site of AChE, a series of novel derivatives of bis- and bifunctional HupB were designed and synthesized. The AChE inhibition potency of most derivatives of HupB was enhanced about 2-3 orders of magnitude as compared with the parental HupB. Among bis-HupB derivatives, 12h exhibited the most potent in the AChE inhibition and has been evaluated for its pharmacological actions in vivo on ChE inhibition, cognitive enhancement, and neuroprotection. The docking study on the bis-HupB derivatives 12 series with TcAChE has demonstrated that the ligands bound to the dual-site of the enzyme in different level. (c) 2006 Elsevier Ltd. All rights reserved.