(Z)-(+/-)-11-ethylidene-9,10-dihydro-2-methoxy-7-methyl-5,9-methanocyclooctapyridine-5(6H)-carboxylic acid methyl ester | 173328-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-(+/-)-11-ethylidene-9,10-dihydro-2-methoxy-7-methyl-5,9-methanocyclooctapyridine-5(6H)-carboxylic acid methyl ester
• 英文别名: (Z)-(+/-)-11-ethylidene-9,10-dihydro-2-methoxy-7-methyl-5,9-methanocycloocta[b]pyridine-5(6H)-carboxylic acid methyl ester；Methyl 13-ethylidene-5-methoxy-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraene-1-carboxylate
• CAS: 173328-00-2
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: HYPRSWDGWDBYQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,4-环己二酮单乙二醇缩酮 在 4-二甲氨基吡啶 、 palladium diacetate 、 Wilkinson's catalyst 、 三苯基膦 盐酸 、 偶氮二异丁腈 、 oxonium 、 氨 、 sodium acetate 、 potassium hydride 、 sodium hydride 、 三乙胺 、 silver carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 溶剂黄146 、 丙酮 为溶剂， 反应 71.0h， 生成 (Z)-(+/-)-11-ethylidene-9,10-dihydro-2-methoxy-7-methyl-5,9-methanocyclooctapyridine-5(6H)-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of huperzine A, its analogs, and their anticholinesterase activity

  摘要：

  Huperzine A is a new alkaloid isolated from the club moss Huperzia serrata (Thunb.) Trev., a Chinese folk medicine. This alkaloid exhibits potent activity as an inhibitor of acetylcholinesterase. Consequently, the compound is presently being investigated in China for the treatment of individuals suffering from various forms of memory impairment including Alzheimer's dementia. Details of the total synthesis of (+/-)-huperzine A are described as well as the preparation of a variety of huperzine analogues including its presumed pharmacophore. The extent of these new compounds to inhibit acetylcholinesterase is presented along with a discussion of the effects of the structural changes on biological activity.

  DOI：

  10.1021/jo00015a014

文献信息

• Synthetic chemistry, neurotransmission and second messengers
  作者：Alan P. Kozikowski

  DOI：10.1002/jhet.5570270108

  日期：1990.1
• Synthesis and biological evaluation of (±)-Z-huperzine A
  作者：Alan P. Kozikowski、Fumio Yamada、X.-C. Tang、Israel Hanin

  DOI：10.1016/s0040-4039(00)97013-8

  日期：1990.1
• Synthesis of huperzine A, its analogs, and their anticholinesterase activity
  作者：Alan P. Kozikowski、Yan Xia、E. Rajarathnam Reddy、Werner Tuckmantel、Israel Hanin、X. C. Tang

  DOI：10.1021/jo00015a014

  日期：1991.7

  Huperzine A is a new alkaloid isolated from the club moss Huperzia serrata (Thunb.) Trev., a Chinese folk medicine. This alkaloid exhibits potent activity as an inhibitor of acetylcholinesterase. Consequently, the compound is presently being investigated in China for the treatment of individuals suffering from various forms of memory impairment including Alzheimer's dementia. Details of the total synthesis of (+/-)-huperzine A are described as well as the preparation of a variety of huperzine analogues including its presumed pharmacophore. The extent of these new compounds to inhibit acetylcholinesterase is presented along with a discussion of the effects of the structural changes on biological activity.