(4Z,12bS)-4-[[[(2E)-3,7-dimethylocta-2,6-dienyl]amino]methylidene]-5-hydroxy-12b-methyl-1,2-dihydrobenzo[a]anthracene-3,6,8,11-tetrone | 1276044-68-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (4Z,12bS)-4-[[[(2E)-3,7-dimethylocta-2,6-dienyl]amino]methylidene]-5-hydroxy-12b-methyl-1,2-dihydrobenzo[a]anthracene-3,6,8,11-tetrone
• CAS: 1276044-68-8
• 化学式: C₃₀H₃₁NO₅
• 分子量: 485.58
• InChiKey: FNZBUQICLHBVJP-UYYJKTCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  100.54
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  香叶胺 、 (12bS)-12b-甲基-1H-四苯o[5,4-Bc]呋喃-3,6,8,11(2H,12bH)-四酮 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以78%的产率得到(4Z,12bS)-4-[[[(2E)-3,7-dimethylocta-2,6-dienyl]amino]methylidene]-5-hydroxy-12b-methyl-1,2-dihydrobenzo[a]anthracene-3,6,8,11-tetrone
  参考文献：
  名称：

  Chemical and biological explorations of the electrophilic reactivity of the bioactive marine natural product halenaquinone with biomimetic nucleophiles

  摘要：

  The electrophilic reactivity of the bioactive marine sponge natural product halenaquinone has been investigated by reaction with the biomimetic nucleophiles N-acetyl-L-cysteine and N-alpha-acetyl-L-lysine. While cysteine reacted at the vacant quinone positions C-14 and C-15, lysine was found to react preferentially at the keto-furan position C-1. A small library of analogues was prepared by reaction of halenaquinone with primary amines, and evaluated against a range of biological targets including phospholipase A(2), farnesyltransferases (FTases) and Plasmodium falciparum. Geranylamine analogue 11 exhibited the most potent activity towards FTases (IC50 0.017-0.031 mu M) and malaria (IC50 0.53-0.62 mu M). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.056

文献信息

• Chemical and biological explorations of the electrophilic reactivity of the bioactive marine natural product halenaquinone with biomimetic nucleophiles
  作者：Jiayi Wang、Marie-Lise Bourguet-Kondracki、Arlette Longeon、Joëlle Dubois、Alexis Valentin、Brent R. Copp

  DOI：10.1016/j.bmcl.2010.12.056

  日期：2011.2

  The electrophilic reactivity of the bioactive marine sponge natural product halenaquinone has been investigated by reaction with the biomimetic nucleophiles N-acetyl-L-cysteine and N-alpha-acetyl-L-lysine. While cysteine reacted at the vacant quinone positions C-14 and C-15, lysine was found to react preferentially at the keto-furan position C-1. A small library of analogues was prepared by reaction of halenaquinone with primary amines, and evaluated against a range of biological targets including phospholipase A(2), farnesyltransferases (FTases) and Plasmodium falciparum. Geranylamine analogue 11 exhibited the most potent activity towards FTases (IC50 0.017-0.031 mu M) and malaria (IC50 0.53-0.62 mu M). (C) 2010 Elsevier Ltd. All rights reserved.