N-[(1S)-1-({2-[(2-{4-[(2-{[2-(4-{[2-({2-[(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-phenylpropanamido]ethyl}disulfanyl)ethyl]carbamoyl}butanamido)ethyl]disulfanyl}ethyl)carbamoyl]butanamido}ethyl)disulfanyl]ethyl}carbamoyl)-2-phenylethyl]carbamic acid tert-butyl ester | 1313492-41-9

• 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-[(1S)-1-({2-[(2-{4-[(2-{[2-(4-{[2-({2-[(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-phenylpropanamido]ethyl}disulfanyl)ethyl]carbamoyl}butanamido)ethyl]disulfanyl}ethyl)carbamoyl]butanamido}ethyl)disulfanyl]ethyl}carbamoyl)-2-phenylethyl]carbamic acid tert-butyl ester
• CAS: 1313492-41-9
• 化学式: C₅₀H₇₈N₈O₁₀S₆
• 分子量: 1143.61
• InChiKey: GLYLOTJFGRSYTB-ZAQUEYBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  74.0
• 可旋转键数：
  37.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  251.26
• 氢给体数：
  8.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  N-[(1S)-1-({2-[(2-{4-[(2-{[2-(4-{[2-({2-[(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-phenylpropanamido]ethyl}disulfanyl)ethyl]carbamoyl}butanamido)ethyl]disulfanyl}ethyl)carbamoyl]butanamido}ethyl)disulfanyl]ethyl}carbamoyl)-2-phenylethyl]carbamic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以90%的产率得到N'-[2-[2-[[(2S)-2-amino-3-phenylpropanoyl]amino]ethyldisulfanyl]ethyl]-N-[2-[2-[[5-[2-[2-[[(2S)-2-amino-3-phenylpropanoyl]amino]ethyldisulfanyl]ethylamino]-5-oxopentanoyl]amino]ethyldisulfanyl]ethyl]pentanediamide;hydrochloride
  参考文献：
  名称：

  Synthesis and in vitro evaluation of novel pro-drugs for the treatment of nephropathic cystinosis

  摘要：

  As part of our continuing work to obtain new pro-drugs for the treatment of nephropathic cystinosis, a number of glutaric and succinic acid derivatives of cystamine have been designed, synthesised and biologically evaluated in vitro. These compounds have been designed as odourless and tasteless pro-drugs which will release multiple molecules of cysteamine upon administration. All of the synthesised compounds evaluated in this study were non-cytotoxic and displayed a greater ability than cysteamine to deplete the levels of cystine in cultured fibroblasts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.022
• 作为产物：
  描述：

  N,N'-diglutaroylcystamine 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N-[(1S)-1-({2-[(2-{4-[(2-{[2-(4-{[2-({2-[(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-phenylpropanamido]ethyl}disulfanyl)ethyl]carbamoyl}butanamido)ethyl]disulfanyl}ethyl)carbamoyl]butanamido}ethyl)disulfanyl]ethyl}carbamoyl)-2-phenylethyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and in vitro evaluation of novel pro-drugs for the treatment of nephropathic cystinosis

  摘要：

  As part of our continuing work to obtain new pro-drugs for the treatment of nephropathic cystinosis, a number of glutaric and succinic acid derivatives of cystamine have been designed, synthesised and biologically evaluated in vitro. These compounds have been designed as odourless and tasteless pro-drugs which will release multiple molecules of cysteamine upon administration. All of the synthesised compounds evaluated in this study were non-cytotoxic and displayed a greater ability than cysteamine to deplete the levels of cystine in cultured fibroblasts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.022