(S)-2-[N(2)-[(tert-butyloxy)carbonyl]amino]-N-methoxyl-N-methyl-5-hexenoic amide | 208522-14-9

• 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: (S)-2-[N(2)-[(tert-butyloxy)carbonyl]amino]-N-methoxyl-N-methyl-5-hexenoic amide
• 英文别名: tert-butyl N-[(2S)-1-[methoxy(methyl)amino]-1-oxohex-5-en-2-yl]carbamate
• CAS: 208522-14-9
• 化学式: C₁₃H₂₄N₂O₄
• 分子量: 272.345
• InChiKey: PLZAHSMZSIEELI-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-[N(2)-[(tert-butyloxy)carbonyl]amino]-N-methoxyl-N-methyl-5-hexenoic amide 在 4-二甲氨基吡啶 四氢化物钛 、 lithium aluminium tetrahydride 、 Grubbs catalyst first generation 、 TEA 、 氢气 、 铜 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hexamethyldisilazane 、 锌 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 [(3S,6S,13S)-3-Methyl-13-((2S,4R)-4-methyl-5-oxo-tetrahydro-furan-2-yl)-2,5-dioxo-1,4-diaza-cyclotridec-6-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Macrocyclic peptidomimetic inhibitors of β-secretase (BACE): First X-ray structure of a macrocyclic peptidomimetic-BACE complex

  摘要：

  The synthesis of novel macrocyclic peptidomimetic inhibitors of the enzyme BACE1 is described. These macrocycles are derived from a hydroxypthylene core structure. Compound 7 was co-crystallized with BACE1 and the X-ray structure of the complex elucidated at 1.6 angstrom resolution. This molecule inhibits the production of the A beta peptide in HEK293 cells overexpressing APP751sw. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.003
• 作为产物：
  描述：

  (S)-2-tert-butoxycarbonylamino-hex-5-enoic acid methyl ester 在 N-甲基吗啉 、 caesium carbonate 、 氯甲酸异丁酯 作用下， 生成 (S)-2-[N(2)-[(tert-butyloxy)carbonyl]amino]-N-methoxyl-N-methyl-5-hexenoic amide
  参考文献：
  名称：

  Macrocyclic peptidomimetic inhibitors of β-secretase (BACE): First X-ray structure of a macrocyclic peptidomimetic-BACE complex

  摘要：

  The synthesis of novel macrocyclic peptidomimetic inhibitors of the enzyme BACE1 is described. These macrocycles are derived from a hydroxypthylene core structure. Compound 7 was co-crystallized with BACE1 and the X-ray structure of the complex elucidated at 1.6 angstrom resolution. This molecule inhibits the production of the A beta peptide in HEK293 cells overexpressing APP751sw. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.003

文献信息

• Synthesis of macrocyclic trypanosomal cysteine protease inhibitors
  作者：Yen Ting Chen、Ricardo Lira、Elizabeth Hansell、James H. McKerrow、William R. Roush

  DOI：10.1016/j.bmcl.2008.06.012

  日期：2008.11

  The importance of cysteine proteases in parasites, compounded with the lack of redundancy compared to their mammalian hosts makes proteases attractive targets for the development of new therapeutic agents. The binding mode of K11002 to cruzain, the major cysteine protease of Trypanosoma cruzi was used in the design of conformationally constrained inhibitors. Vinyl sulfone-containing macrocycles were

  半胱氨酸蛋白酶在寄生虫中的重要性，再加上与其哺乳动物宿主相比缺乏冗余，使得蛋白酶成为开发新治疗剂的有吸引力的目标。K11002 与 cruzain（克氏锥虫的主要半胱氨酸蛋白酶）的结合模式被用于构象受限抑​​制剂的设计。含乙烯基砜的大环化合物是通过烯烃闭环复分解合成的，并针对 cruzain 和密切相关的半胱氨酸蛋白酶罗得沙因进行了评估。
• Macrocyclic peptidomimetic inhibitors of β-secretase (BACE): First X-ray structure of a macrocyclic peptidomimetic-BACE complex
  作者：Isabel Rojo、José Alfredo Martín、Howard Broughton、David Timm、Jon Erickson、Hsiu-Chiung Yang、James R. McCarthy

  DOI：10.1016/j.bmcl.2005.09.003

  日期：2006.1

  The synthesis of novel macrocyclic peptidomimetic inhibitors of the enzyme BACE1 is described. These macrocycles are derived from a hydroxypthylene core structure. Compound 7 was co-crystallized with BACE1 and the X-ray structure of the complex elucidated at 1.6 angstrom resolution. This molecule inhibits the production of the A beta peptide in HEK293 cells overexpressing APP751sw. (c) 2005 Elsevier Ltd. All rights reserved.