anthranoyllycoctonine | 22413-78-1

• 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: anthranoyllycoctonine
• 英文别名: inuline；[(1S,2R,3R,4S,5R,6S,8R,9S,13S,16S,17R,18S)-11-ethyl-8,9-dihydroxy-4,6,16,18-tetramethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-13-yl]methyl 2-aminobenzoate
• CAS: 22413-78-1
• 化学式: C₃₂H₄₆N₂O₈
• 分子量: 586.726
• InChiKey: NNDHDYDFEDRMGH-CAEIVAEBSA-N

物化性质

• 沸点：
  642.86°C (rough estimate)
• 密度：
  1.1777 (rough estimate)
• 熔点：
  154-155 °C(Solv: ethanol (64-17-5))

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  [3H]-methyllycaconitine 在 4-二甲氨基吡啶 、 氢氧化钾 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 anthranoyllycoctonine
  参考文献：
  名称：

  Nudicauline and Elatine as Potent Norditerpenoid Ligands at Rat Neuronal α-Bungarotoxin Binding Sites:  Importance of the 2-(Methylsuccinimido)benzoyl Moiety for Neuronal Nicotinic Acetylcholine Receptor Binding

  摘要：

  Methyllycaconitine (MLA, 1) is a novel, potent probe for mammalian and insect nicotinic acetylcholine receptors (nAChR) and displays remarkable selectivity toward neuronal [I-125]- alpha-bungarotoxin (alpha BgTX) binding sites that correspond to alpha 7-type nAChR in mammalian brain. We have shown that, among a number of selected norditerpenoid alkaloids, elatine (2) and nudicauline (3) are equipotent with, or better than, MLA (1) in binding to brain [I-125]-alpha BgTX binding sites, with IC50 values of 6.1, 1.7, and 7.6 nM, respectively. The 2-((S)-methylsuccinimido)benzoyl moiety of these Ligands is crucial for high-affinity binding, whereas structural modifications to the norditerpenoid core of the ligand can be tolerated without loss of activity or selectivity. In addition to MLA (1), elatine (2), and nudicauline (3), we have examined lycoctonine (4), inuline (6), lappaconitine (7), N-desacetyllappaconitine (8), delsoline (10), delcorine (11), deltaline (12), condelphine (13), and karacoline (14). This study therefore extends the range of norditerpenoids, other than MLA, which can be used to probe this important class of nAChR. All 12 alkaloids were assessed for activity at [H-3]nicotine binding sites which are considered to represent alpha 4 beta 2 nAChR. Furthermore, the H-1 and C-13 NMR spectroscopic data of MLA and elatine have been critically compared.

  DOI：

  10.1021/jm9604991

文献信息

• Pelletier, S. William; Desai, Haridutt K.; Kulathaivel, Palaniappan, Heterocycles, 1987, vol. 26, # 11, p. 2835 - 2840
  作者：Pelletier, S. William、Desai, Haridutt K.、Kulathaivel, Palaniappan、Joshi, Balawant S.

  DOI：——

  日期：——
• Nudicauline and Elatine as Potent Norditerpenoid Ligands at Rat Neuronal α-Bungarotoxin Binding Sites:  Importance of the 2-(Methylsuccinimido)benzoyl Moiety for Neuronal Nicotinic Acetylcholine Receptor Binding
  作者：David J. Hardick、Ian S. Blagbrough、Gary Cooper、Barry V. L. Potter、Trevor Critchley、Susan Wonnacott

  DOI：10.1021/jm9604991

  日期：1996.1.1

  Methyllycaconitine (MLA, 1) is a novel, potent probe for mammalian and insect nicotinic acetylcholine receptors (nAChR) and displays remarkable selectivity toward neuronal [I-125]- alpha-bungarotoxin (alpha BgTX) binding sites that correspond to alpha 7-type nAChR in mammalian brain. We have shown that, among a number of selected norditerpenoid alkaloids, elatine (2) and nudicauline (3) are equipotent with, or better than, MLA (1) in binding to brain [I-125]-alpha BgTX binding sites, with IC50 values of 6.1, 1.7, and 7.6 nM, respectively. The 2-((S)-methylsuccinimido)benzoyl moiety of these Ligands is crucial for high-affinity binding, whereas structural modifications to the norditerpenoid core of the ligand can be tolerated without loss of activity or selectivity. In addition to MLA (1), elatine (2), and nudicauline (3), we have examined lycoctonine (4), inuline (6), lappaconitine (7), N-desacetyllappaconitine (8), delsoline (10), delcorine (11), deltaline (12), condelphine (13), and karacoline (14). This study therefore extends the range of norditerpenoids, other than MLA, which can be used to probe this important class of nAChR. All 12 alkaloids were assessed for activity at [H-3]nicotine binding sites which are considered to represent alpha 4 beta 2 nAChR. Furthermore, the H-1 and C-13 NMR spectroscopic data of MLA and elatine have been critically compared.