N-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl}-N'-{2-[2-(4-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethylcarbamoyl}-butyrylamino)-ethyldisulfanyl]-ethyl}-butyryamide | 1268342-49-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl}-N'-{2-[2-(4-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethylcarbamoyl}-butyrylamino)-ethyldisulfanyl]-ethyl}-butyryamide
• 英文别名: N-[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-N'-[2-[2-[[5-[2-[2-(2-methoxyethoxy)ethoxy]ethylamino]-5-oxopentanoyl]amino]ethyldisulfanyl]ethyl]pentanediamide
• CAS: 1268342-49-9
• 化学式: C₂₈H₅₄N₄O₁₀S₂
• 分子量: 670.89
• InChiKey: ZYNSTOINBVHDCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  44
• 可旋转键数：
  33
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  222
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  5-imidazol-1-yl-5-oxo-pentanoic acid {2-[2-(5-imidazol-1-yl-5-oxo-pentanoylamino)ethyldisulfanyl]ethyl}amide 、 3,6,9-三氧杂-1-氨基癸烷 以 N,N-二甲基甲酰胺 为溶剂， 以64%的产率得到N-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl}-N'-{2-[2-(4-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethylcarbamoyl}-butyrylamino)-ethyldisulfanyl]-ethyl}-butyryamide
  参考文献：
  名称：

  PEGylated derivatives of cystamine as enhanced treatments for nephropathic cystinosis

  摘要：

  The genetic disease, nephropathic cystinosis is characterized by lysosomal accumulation of the amino acid cystine. Crystallization of cystine in affected organs, if untreated, results in mortality of the affected individuals by their middle to late teens. The only approved treatment for cystinosis is administration of cysteamine. However, cysteamine is associated with an offending odor and taste and this, coupled to a rapid first pass metabolism and a 6 h dosing regimen, suggest a clear need to improve the therapy. A number of PEGylated derivatives of cystamine, the disulfide counterpart of cysteamine, have been synthesised and evaluated in cultured cystinotic fibroblasts for toxicity and efficacy. All of the tested compounds were non-cytotoxic and displayed a remarkable depletion of intralysosomal cystine. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.085

文献信息

• PEGylated derivatives of cystamine as enhanced treatments for nephropathic cystinosis
  作者：Ziad Omran、Graeme Kay、Alberto Di Salvo、Rachel M. Knott、Donald Cairns

  DOI：10.1016/j.bmcl.2010.11.085

  日期：2011.1

  The genetic disease, nephropathic cystinosis is characterized by lysosomal accumulation of the amino acid cystine. Crystallization of cystine in affected organs, if untreated, results in mortality of the affected individuals by their middle to late teens. The only approved treatment for cystinosis is administration of cysteamine. However, cysteamine is associated with an offending odor and taste and this, coupled to a rapid first pass metabolism and a 6 h dosing regimen, suggest a clear need to improve the therapy. A number of PEGylated derivatives of cystamine, the disulfide counterpart of cysteamine, have been synthesised and evaluated in cultured cystinotic fibroblasts for toxicity and efficacy. All of the tested compounds were non-cytotoxic and displayed a remarkable depletion of intralysosomal cystine. (C) 2010 Elsevier Ltd. All rights reserved.