4-{4-[(2R,3R,4R,5R)-2,3,5,6-Tetrahydroxy-4-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexanoyl]-piperazin-1-yl}-benzaldehyde | 918802-83-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-{4-[(2R,3R,4R,5R)-2,3,5,6-Tetrahydroxy-4-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexanoyl]-piperazin-1-yl}-benzaldehyde
• CAS: 918802-83-2
• 化学式: C₂₃H₃₄N₂O₁₂
• 分子量: 530.529
• InChiKey: GYYCNQRWHKJSHC-ZGPJYTKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.59
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  220.92
• 氢给体数：
  8.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  4-{4-[(2R,3R,4R,5R)-2,3,5,6-Tetrahydroxy-4-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexanoyl]-piperazin-1-yl}-benzaldehyde 、 吡咯 在 丙酸 作用下， 反应 0.5h， 以13.5%的产率得到5,10,15,20-tetra[4-(4'-galactosylpiperazinyl)phenyl]porphyrin
  参考文献：
  名称：

  Study on synthesis and biological activity of a galactosylated piperazinyl porphyrin

  摘要：

  In order to obtain an carcinoma-selective drug, the synthesis and characterization of. 5,10,15,20-tetra[4-(4'-galactosylpiperazinyl)phenyl]porphyrin (TGPP) is reported. The biological activity on cancer cells and the pharmacokinetics are also reported as preliminary results showing a very high liver to skin ratio and short retention time in tissues, and thus promising activity in photodynamic therapy. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.020
• 作为产物：
  描述：

  N-苯基哌嗪 在 四甲基乙二胺 、 N,N'-二环己基碳二亚胺 、 三氯氧磷 作用下， 生成 4-{4-[(2R,3R,4R,5R)-2,3,5,6-Tetrahydroxy-4-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexanoyl]-piperazin-1-yl}-benzaldehyde
  参考文献：
  名称：

  Study on synthesis and biological activity of a galactosylated piperazinyl porphyrin

  摘要：

  In order to obtain an carcinoma-selective drug, the synthesis and characterization of. 5,10,15,20-tetra[4-(4'-galactosylpiperazinyl)phenyl]porphyrin (TGPP) is reported. The biological activity on cancer cells and the pharmacokinetics are also reported as preliminary results showing a very high liver to skin ratio and short retention time in tissues, and thus promising activity in photodynamic therapy. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.020

文献信息

• Synthesis of lactosylated piperazinyl porphyrins and their hepatocyte-selective targeting
  作者：He-Ping Li、Zhong Cao、Hua-Wu Xiao

  DOI：10.1007/s00044-007-9007-x

  日期：2008.1

  The aim of this work was the synthesis of a new family of lactosylated piperazinly porphyrins in which the galactoside piperazine moieties are linked to the tetra- and monophenyl ring by an amide bond. Two compounds were designed, synthesized, and characterized by H-1-nuclear magnetic resonance (H-1-NMR), ultraviolet (UV)-visible, and matrix-assisted laser desorption/ionization (MALDI) mass spectra. The biological activity on cancer cells and the pharmacokinetics have also been evaluated, showing a very high liver-to-skin ratio and short retention time in tissues. It is suggested that such novel lactosylated piperazinyl porphyrins, as potential hepatocyte-selective targeting drugs, thus show promising activity in photodynamic therapy.