(S)-(+)-aegeline

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (S)-(+)-aegeline
• 英文别名: (S)-(-)-aegeline；(-)-aegeline；(E)-N-[(2S)-2-hydroxy-2-(4-methoxyphenyl)ethyl]-3-phenylprop-2-enamide
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: QRFDENJATPJOKG-SNQZOLJRSA-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：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-azido-1-(4-methoxyphenyl)ethanol 在 palladium on activated charcoal Pseudomonas cepacia lipase immobilized on ceramic particles 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 异丙醚 为溶剂， 20.0~40.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 (S)-(+)-aegeline
  参考文献：
  名称：

  Chemoenzymatic synthesis of (R)- and (S)-tembamide, aegeline and denopamine by a one-pot lipase resolution protocol

  摘要：

  An efficient synthesis of optically active beta-azido alcohols from their ketoazides by a one-pot reduction and an in situ lipase resolution protocol is described. The synthetic utility of this procedure has been illustrated by its application in the practical synthesis of both enantiomers of the natural hydroxyamides, tembamide, aegeline and the cardiac drug denopamine, with high enantioselectivities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.013

文献信息

• Simultaneous Determination of Aegeline and Six Coumarins from Different Parts of the Plant Aegle marmelos Using UHPLC-PDA-MS and Chiral Separation of Aegeline Enantiomers Using HPLC-ToF-MS
  作者：Bharathi Avula、Amar Chittiboyina、Yan-Hong Wang、Satyanarayanaraju Sagi、Vijayasankar Raman、Mei Wang、Ikhlas Khan

  DOI：10.1055/s-0042-103160

  日期：——

  A fast UHPLC-PDA method was developed for the simultaneous analysis of one alkaloid, aegeline, and six coumarins, viz., umbelliferone, scopoletin, marmesinin, 8-hydroxypsoralen, angelicin, and marmelosin, from the leaf, fruit, root, and bark of Aegle marmelos. The UHPLC method was validated for linearity, accuracy, repeatability, limits of detection and limits of quantification. The linearity range

  开发了一种快速 UHPLC-PDA 方法，用于同时分析叶、果实、根和树皮中的一种生物碱、aegeline 和 6 种香豆素，即伞形酮、东莨菪碱、marmesinin、8-羟基补骨脂素、当归素和 marmelosin Aegle 马梅洛斯。UHPLC 方法的线性度、准确度、重复性、检测限和定量限均经过验证。七种化合物的线性范围 (r(2) > 0.99) 为 0.5-250 µg/mL，七种化合物的检测限和定量限分别为 0.1 和 0.5 µg/mL，分别。开发的 UHPLC 方法简单、快速，特别适用于 A. marmelos 和商业膳食补充剂中香豆素和 aegeline 的质量控制分析。单四极杆质谱用于鉴定和确认来自不同植物部位和膳食补充剂的香豆素和 aegeline。此外，还开发了一种新的手性 HPLC-ToF-MS 方法来拆分 aegeline 对映异构体。通过应用这种手性方法，首次报道了来自
• Phenylethyl cinnamides: A new series of α-glucosidase inhibitors from the leaves of Aegle marmelos
  作者：Preecha Phuwapraisirisan、Thanchanok Puksasook、Jonkolnee Jong-aramruang、Udom Kokpol

  DOI：10.1016/j.bmcl.2008.08.024

  日期：2008.9

  A series of phenylethyl cinnamides, which included new compounds named anhydromarmeline (1), aegelinosides A (7) and B (8), were isolated from Aegle marmelos leaves as a-glucosidase inhibitors. The structures of new compounds were characterized by spectroscopic data and chemical degradation. Of compounds isolated, anhydroaegeline (2) revealed the most potent inhibitory effect against a-glucosidase with IC50 value of 35.8 mu M. The present result also supports ethnopharmacological use of A. marmelos as a remedy for diabetes mellitus. (C) 2008 Elsevier Ltd. All rights reserved.
• Chemoenzymatic synthesis of (R)- and (S)-tembamide, aegeline and denopamine by a one-pot lipase resolution protocol
  作者：Ahmed Kamal、Ahmad Ali Shaik、Mahendra Sandbhor、M. Shaheer Malik

  DOI：10.1016/j.tetasy.2004.11.013

  日期：2004.12

  An efficient synthesis of optically active beta-azido alcohols from their ketoazides by a one-pot reduction and an in situ lipase resolution protocol is described. The synthetic utility of this procedure has been illustrated by its application in the practical synthesis of both enantiomers of the natural hydroxyamides, tembamide, aegeline and the cardiac drug denopamine, with high enantioselectivities. (C) 2004 Elsevier Ltd. All rights reserved.