4-((S)-6-(((allyloxy)carbonyl)amino)-2-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)hexanamido)benzyl (2,4,6-tris(((tert-butyldimethylsilyl)oxy)methyl)phenyl)carbamate | 1179988-83-0

• 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: 4-((S)-6-(((allyloxy)carbonyl)amino)-2-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)hexanamido)benzyl (2,4,6-tris(((tert-butyldimethylsilyl)oxy)methyl)phenyl)carbamate
• CAS: 1179988-83-0
• 化学式: C₅₉H₉₅N₅O₁₁Si₃
• 分子量: 1134.69
• InChiKey: NRCGZRDLSUQQFW-GTMCEHENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.64
• 重原子数：
  78.0
• 可旋转键数：
  26.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  200.88
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  4-((S)-6-(((allyloxy)carbonyl)amino)-2-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)hexanamido)benzyl (2,4,6-tris(((tert-butyldimethylsilyl)oxy)methyl)phenyl)carbamate 在 amberlyst-15 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以71%的产率得到4-((S)-6-(((allyloxy)carbonyl)amino)-2-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)hexanamido)benzyl (2,4,6-tris(hydroxymethyl)phenyl)carbamate
  参考文献：
  名称：

  Enhanced cytotoxicity of a polymer–drug conjugate with triple payload of paclitaxel

  摘要：

  The development of targeting approaches to selectively release chemotherapeutic drugs into malignant tissue is a major challenge in anticancer therapy. We have synthesized an N-(2-hydroxypropyl)-methacrylamide (HPMA) copolymer-drug conjugate with an AB(3) self-immolative dendritic linker. HPMA copolymers are known to accumulate selectively in tumors. The water-soluble polymer-drug conjugate was designed to release a triple payload of the hydrophobic drug paclitaxel as a result of cleavage by the endogenous enzyme cathepsin B. The polymer-drug conjugate exhibited enhanced cytotoxicity on murine prostate adenocarcinoma (TRAMP C2) cells in comparison to a classic monomeric drug-polymer conjugate. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.028
• 作为产物：
  描述：

  、 tert-butyl ((S)-1-(((S)-6-(((allyloxy)carbonyl)amino)-1-((4-(hydroxymethyl)phenyl)amino)-1-oxohexan-2-yl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以52%的产率得到4-((S)-6-(((allyloxy)carbonyl)amino)-2-((S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)hexanamido)benzyl (2,4,6-tris(((tert-butyldimethylsilyl)oxy)methyl)phenyl)carbamate
  参考文献：
  名称：

  Enhanced cytotoxicity of a polymer–drug conjugate with triple payload of paclitaxel

  摘要：

  The development of targeting approaches to selectively release chemotherapeutic drugs into malignant tissue is a major challenge in anticancer therapy. We have synthesized an N-(2-hydroxypropyl)-methacrylamide (HPMA) copolymer-drug conjugate with an AB(3) self-immolative dendritic linker. HPMA copolymers are known to accumulate selectively in tumors. The water-soluble polymer-drug conjugate was designed to release a triple payload of the hydrophobic drug paclitaxel as a result of cleavage by the endogenous enzyme cathepsin B. The polymer-drug conjugate exhibited enhanced cytotoxicity on murine prostate adenocarcinoma (TRAMP C2) cells in comparison to a classic monomeric drug-polymer conjugate. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.028