5-[1,2]Dithiolan-3-yl-pentanoic acid (2-{(S)-1-[(S)-1-(4-chloro-benzyl)-2-ethylcarbamoyl-2-hydroxy-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-ethyl)-amide | 949882-67-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: 5-[1,2]Dithiolan-3-yl-pentanoic acid (2-{(S)-1-[(S)-1-(4-chloro-benzyl)-2-ethylcarbamoyl-2-hydroxy-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-ethyl)-amide
• CAS: 949882-67-1
• 化学式: C₂₈H₄₃ClN₄O₅S₂
• 分子量: 615.258
• InChiKey: WGIUBCPZXXGCIU-WWLAAKCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  40.0
• 可旋转键数：
  17.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  136.63
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-[1,2]Dithiolan-3-yl-pentanoic acid (2-{(S)-1-[(S)-1-(4-chloro-benzyl)-2-ethylcarbamoyl-2-hydroxy-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-ethyl)-amide 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (2S)-N-[(2S)-1-(4-chlorophenyl)-4-(ethylamino)-3,4-dioxobutan-2-yl]-2-[3-[5-(dithiolan-3-yl)pentanoylamino]propanoylamino]-3-methylbutanamide
  参考文献：
  名称：

  Novel cell-penetrating α-keto-amide calpain inhibitors as potential treatment for muscular dystrophy

  摘要：

  Dipeptide-derived alpha-keto-amide compounds with potent calpain inhibitory activity have been identified. These reversible covalent inhibitors have IC50 values down to 25 nM and exhibit greatly improved activity in muscle cells compared to the reference compound MDL28170. Several novel calpain inhibitors have shown positive effects on histological parameters in an animal model of Duchenne muscular dystrophy demonstrating their potential as a treatment option for this fatal disease. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.064
• 作为产物：
  描述：

  tert-butyl (S)-(1-(4-chlorophenyl)-3-oxopropan-2-yl)carbamate 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-[1,2]Dithiolan-3-yl-pentanoic acid (2-{(S)-1-[(S)-1-(4-chloro-benzyl)-2-ethylcarbamoyl-2-hydroxy-ethylcarbamoyl]-2-methyl-propylcarbamoyl}-ethyl)-amide
  参考文献：
  名称：

  Novel cell-penetrating α-keto-amide calpain inhibitors as potential treatment for muscular dystrophy

  摘要：

  Dipeptide-derived alpha-keto-amide compounds with potent calpain inhibitory activity have been identified. These reversible covalent inhibitors have IC50 values down to 25 nM and exhibit greatly improved activity in muscle cells compared to the reference compound MDL28170. Several novel calpain inhibitors have shown positive effects on histological parameters in an animal model of Duchenne muscular dystrophy demonstrating their potential as a treatment option for this fatal disease. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.08.064