2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl-[2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]acetyl]amino]acetic acid | 1415728-15-2

• 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: 2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl-[2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]acetyl]amino]acetic acid
• CAS: 1415728-15-2
• 化学式: C₃₆H₄₄N₂O₉
• 分子量: 648.753
• InChiKey: UKXFTLUYDKCEGG-JFKGNKFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  47
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[2-aminoethyl-[2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]acetyl]amino]acetate 、 2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl-[2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]acetyl]amino]acetic acid 在 2,6-二甲基吡啶 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 以88%的产率得到tert-butyl 2-[2-[[2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl-[2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]acetyl]amino]acetyl]amino]ethyl-[2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]acetyl]amino]acetate
  参考文献：
  名称：

  Facile synthesis and anticancer activity of C-10 non-acetal deoxoartemisinin dimers

  摘要：

  In this research, N-(2-aminoethyl)glycine-linked C-10 non-acetal deoxoartemisinin dimers were synthesized by using solution phase peptide synthesis approach. In addition, chemical modification of the C-10 non-acetal deoxoartemisinin monomers and dimers by adding a lysine unit to the N-terminus has been performed. The biological activities of all synthesized compounds were evaluated against the colon cancer cell line (Caco-2). The non-acetal deoxoartemisinin monomers 12a, 15a-c and dimers 13a, 16a-c were active against Caco-2 cells and more potent than dihydroartemisinin. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.020
• 作为产物：
  描述：

  双氢青蒿素 在 吡啶 、 2,6-二甲基吡啶 、 potassium permanganate 、 sodium periodate 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 64.5h， 生成 2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl-[2-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]acetyl]amino]acetic acid
  参考文献：
  名称：

  Facile synthesis and anticancer activity of C-10 non-acetal deoxoartemisinin dimers

  摘要：

  In this research, N-(2-aminoethyl)glycine-linked C-10 non-acetal deoxoartemisinin dimers were synthesized by using solution phase peptide synthesis approach. In addition, chemical modification of the C-10 non-acetal deoxoartemisinin monomers and dimers by adding a lysine unit to the N-terminus has been performed. The biological activities of all synthesized compounds were evaluated against the colon cancer cell line (Caco-2). The non-acetal deoxoartemisinin monomers 12a, 15a-c and dimers 13a, 16a-c were active against Caco-2 cells and more potent than dihydroartemisinin. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.020