N-(4-{[3-((4-benzothiazol-2-yl-benzyl)-{4-[3,5-bis-(4-hydroxy-3-methoxy-benzylidene)-4-oxo-piperidin-1-yl]-4-oxo-butyryl}-amino)-propyl]-tert-butoxycarbonyl-amino}-butyl)-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester | 1247874-49-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(4-{[3-((4-benzothiazol-2-yl-benzyl)-{4-[3,5-bis-(4-hydroxy-3-methoxy-benzylidene)-4-oxo-piperidin-1-yl]-4-oxo-butyryl}-amino)-propyl]-tert-butoxycarbonyl-amino}-butyl)-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[3-[[4-(1,3-benzothiazol-2-yl)phenyl]methyl-[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: 1247874-49-2
• 化学式: C₆₄H₈₂N₆O₁₃S
• 分子量: 1175.45
• InChiKey: NQFXKCIDKBABPQ-TZRJFHBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  84
• 可旋转键数：
  29
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  255
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  N-(4-{[3-((4-benzothiazol-2-yl-benzyl)-{4-[3,5-bis-(4-hydroxy-3-methoxy-benzylidene)-4-oxo-piperidin-1-yl]-4-oxo-butyryl}-amino)-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}-N-(4-benzothiazol-2-yl-benzyl)-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-(4-benzothiazol-2-yl-benzyl)-N-[3-(tert-butoxycarbonyl-{4-[tert-butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-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 N-(4-{[3-((4-benzothiazol-2-yl-benzyl)-{4-[3,5-bis-(4-hydroxy-3-methoxy-benzylidene)-4-oxo-piperidin-1-yl]-4-oxo-butyryl}-amino)-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