tert-butyl (S)-(1-((2-((2-aminoethyl)disulfaneyl)ethyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate | 217655-65-7

• 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: tert-butyl (S)-(1-((2-((2-aminoethyl)disulfaneyl)ethyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
• CAS: 217655-65-7
• 化学式: C₁₈H₂₉N₃O₃S₂
• 分子量: 399.579
• InChiKey: PXRWVQWGCFFGHW-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  26.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  93.45
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-imidazol-1-yl-5-oxo-pentanoic acid {2-[2-(5-imidazol-1-yl-5-oxo-pentanoylamino)ethyldisulfanyl]ethyl}amide 、 tert-butyl (S)-(1-((2-((2-aminoethyl)disulfaneyl)ethyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 以 N,N-二甲基甲酰胺 为溶剂， 以47%的产率得到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
• 作为产物：
  描述：

  cystamine dihydrochioride 、 BOC-L-苯丙氨酸琥珀酰亚胺酯 在 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 以58%的产率得到tert-butyl (S)-(1-((2-((2-aminoethyl)disulfaneyl)ethyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
  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