2-[(S)-2-((S)-2-Cyclohexyl-1-methyl-ethoxycarbonylamino)-1-hydroxy-hexyl]-4-methyl-thiazole-5-carboxylic acid ethyl ester | 865537-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[(S)-2-((S)-2-Cyclohexyl-1-methyl-ethoxycarbonylamino)-1-hydroxy-hexyl]-4-methyl-thiazole-5-carboxylic acid ethyl ester
• CAS: 865537-84-4
• 化学式: C₂₃H₃₈N₂O₅S
• 分子量: 454.631
• InChiKey: XWKNOSXLZLSBOM-SIYBWXAISA-N

物化性质

• 沸点：
  575.9±50.0 °C(predicted)
• 密度：
  1.132±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  31.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  97.75
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-[(S)-2-((S)-2-Cyclohexyl-1-methyl-ethoxycarbonylamino)-1-hydroxy-hexyl]-4-methyl-thiazole-5-carboxylic acid ethyl ester 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 potassium bromide 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl 2-[(2S)-2-[[(2S)-1-cyclohexylpropan-2-yl]oxycarbonylamino]hexanoyl]-4-methyl-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  Ketoheterocycle-based inhibitors of cathepsin K: A novel entry into the synthesis of peptidic ketoheterocycles

  摘要：

  Ketoheterocyclic inhibitors of cathepsin K have been disclosed. SAR of potency enhancing P-2-P-3 groups coupled with ketoheterocyclic warheads to provide cathepsin K inhibitors have been described. In addition, a novel route to access alpha-ketothiazoles using a key thioamide functionality has been disclosed. The mild method employed allows for the presence of diverse functional groups, such as amide and carbamate functionalities, commonly found in protease inhibitors that have peptidomimetic scaffolds. This new method should provide a quick entry into functionally diverse protease inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.091
• 作为产物：
  描述：

  N-Boc-L-正亮氨酸 在 N-甲基吗啉 、 potassium cyanide 、 sodium tetrahydroborate 、 18-冠醚-6 、 三氧化硫吡啶 、 二硫代磷酸二乙酯 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 生成 2-[(S)-2-((S)-2-Cyclohexyl-1-methyl-ethoxycarbonylamino)-1-hydroxy-hexyl]-4-methyl-thiazole-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Ketoheterocycle-based inhibitors of cathepsin K: A novel entry into the synthesis of peptidic ketoheterocycles

  摘要：

  Ketoheterocyclic inhibitors of cathepsin K have been disclosed. SAR of potency enhancing P-2-P-3 groups coupled with ketoheterocyclic warheads to provide cathepsin K inhibitors have been described. In addition, a novel route to access alpha-ketothiazoles using a key thioamide functionality has been disclosed. The mild method employed allows for the presence of diverse functional groups, such as amide and carbamate functionalities, commonly found in protease inhibitors that have peptidomimetic scaffolds. This new method should provide a quick entry into functionally diverse protease inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.091