tert-butyl 2-[2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]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 | 1415728-18-5

• 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: tert-butyl 2-[2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]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
• CAS: 1415728-18-5
• 化学式: C₅₁H₇₂N₄O₁₂
• 分子量: 933.152
• InChiKey: BAXGYSAGBKLOHK-YLGAHFKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  67
• 可旋转键数：
  21
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  189
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]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 在 哌啶 、 盐酸 、 水 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 tert-butyl 2-[2-[[(2S)-2,6-diaminohexanoyl]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 哌啶 、 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-) 、 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 81.0h， 生成 tert-butyl 2-[2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]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

文献信息

• Facile synthesis and anticancer activity of C-10 non-acetal deoxoartemisinin dimers
  作者：Supannee Phothongkam、Sirirat Chancharunee、Angkana Saovapakhiran、Uthai Wichai、Manat Pohmakotr

  DOI：10.1016/j.bmcl.2012.10.020

  日期：2012.12

  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.