{4-[(3-{4-[3,5-bis-(4-hydroxy-3-methoxy-benzylidene)-4-oxo-piperidin-1-yl]-4-oxo-butyrylamino}-propyl)-tert-butoxycarbonyl-amino]-butyl}-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester | 1247874-41-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: {4-[(3-{4-[3,5-bis-(4-hydroxy-3-methoxy-benzylidene)-4-oxo-piperidin-1-yl]-4-oxo-butyrylamino}-propyl)-tert-butoxycarbonyl-amino]-butyl}-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[3-[[4-[(3E,5E)-3,5-bis[(4-hydroxy-3-methoxyphenyl)methylidene]-4-oxopiperidin-1-yl]-4-oxobutanoyl]amino]propyl]-N-[4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]butyl]carbamate
• CAS: 1247874-41-4
• 化学式: C₅₀H₇₃N₅O₁₃
• 分子量: 952.155
• InChiKey: KBHDJMSEGVXHEJ-AQLKTEAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  68
• 可旋转键数：
  26
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  223
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  {4-[(3-{4-[3,5-bis-(4-hydroxy-3-methoxy-benzylidene)-4-oxo-piperidin-1-yl]-4-oxo-butyrylamino}-propyl)-tert-butoxycarbonyl-amino]-butyl}-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester 、 三氟乙酸 以 二氯甲烷 为溶剂， 以100%的产率得到N-{3-[4-(3-amino-propylamino)butylamino]-propyl}-4-[3,5-bis-(4-hydroxy-3-methoxybenzylidene)-4-oxo-piperidin-1-yl]-4-oxo-butyramide trifluoroacetate
  参考文献：
  名称：

  Polyamine Conjugation of Curcumin Analogues toward the Discovery of Mitochondria-Directed Neuroprotective Agents

  摘要：

  Mitochondria-directed antioxidants 2-5 were designed by conjugating curcumin congeners with different polyamine motifs as vehicle tools. The conjugates emerged as efficient antioxidants in mitochondria and fibroblasts and also exerted a protecting role through heme oxygenase-1 activation. Notably, the insertion of a polyamine function into the curcumin-like moiety allowed an efficient intracellular uptake and mitochondria targeting. It also resulted in a significant decrease in the cytotoxicity effects. 2-5 are therefore promising molecules for neuroprotectant lead discovery.

  DOI：

  10.1021/jm100637k
• 作为产物：
  描述：

  3,5-bis(4-hydroxy-3-methoxybenz-(E)-ylidene)-4-piperidone hydrochloride 、 N-[3-(tert-butoxycarbonyl-(4-[tert-butoxycarbonyl-(3-tert-butoxycarbonylaminopropyl)amino]butyl)amino)propyl]succinamic acid 在 1-丙基磷酸酐 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 {4-[(3-{4-[3,5-bis-(4-hydroxy-3-methoxy-benzylidene)-4-oxo-piperidin-1-yl]-4-oxo-butyrylamino}-propyl)-tert-butoxycarbonyl-amino]-butyl}-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Polyamine Conjugation of Curcumin Analogues toward the Discovery of Mitochondria-Directed Neuroprotective Agents

  摘要：

  Mitochondria-directed antioxidants 2-5 were designed by conjugating curcumin congeners with different polyamine motifs as vehicle tools. The conjugates emerged as efficient antioxidants in mitochondria and fibroblasts and also exerted a protecting role through heme oxygenase-1 activation. Notably, the insertion of a polyamine function into the curcumin-like moiety allowed an efficient intracellular uptake and mitochondria targeting. It also resulted in a significant decrease in the cytotoxicity effects. 2-5 are therefore promising molecules for neuroprotectant lead discovery.

  DOI：

  10.1021/jm100637k

文献信息

• Polyamine Conjugation of Curcumin Analogues toward the Discovery of Mitochondria-Directed Neuroprotective Agents
  作者：Elena Simoni、Christian Bergamini、Romana Fato、Andrea Tarozzi、Sandip Bains、Roberto Motterlini、Andrea Cavalli、Maria Laura Bolognesi、Anna Minarini、Patrizia Hrelia、Giorgio Lenaz、Michela Rosini、Carlo Melchiorre

  DOI：10.1021/jm100637k

  日期：2010.10.14

  Mitochondria-directed antioxidants 2-5 were designed by conjugating curcumin congeners with different polyamine motifs as vehicle tools. The conjugates emerged as efficient antioxidants in mitochondria and fibroblasts and also exerted a protecting role through heme oxygenase-1 activation. Notably, the insertion of a polyamine function into the curcumin-like moiety allowed an efficient intracellular uptake and mitochondria targeting. It also resulted in a significant decrease in the cytotoxicity effects. 2-5 are therefore promising molecules for neuroprotectant lead discovery.