(R)-3-Amino-6-phenyl-hexanoic acid | 177839-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-Amino-6-phenyl-hexanoic acid
• 英文别名: (R)-3-Amino-6-phenylhexanoic acid；(3R)-3-amino-6-phenylhexanoic acid
• CAS: 177839-87-1
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: KPJNDHVABVUHPG-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 (R)-3-Amino-6-phenyl-hexanoic acid 在 碳酸氢钠 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以0.3 g的产率得到(R)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-phenylhexanoic acid
  参考文献：
  名称：

  Noncovalent Tripeptidyl Benzyl- and Cyclohexyl-Amine Inhibitors of the Cysteine Protease Caspase-1

  摘要：

  Potent and noncovalent inhibitors of caspase-1 were produced by incorporating a secondary amine (reduced amide) isostere in place of the conventional electrophile (e.g., aldehyde) that normally confers high potency to cysteine protease inhibitors. Benzyl- or cyclohexylamines produced potent, reversible, and competitive inhibitors that were selective for caspase-1 (e.g., K-i = 47 nM) over caspases 3 and 8 with minimal cytotoxicity. Unlike most cysteine protease inhibitors, these compounds do not react covalently and indiscriminately with thiols.

  DOI：

  10.1021/jm901790w
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 反应 0.25h， 生成 (R)-3-Amino-6-phenyl-hexanoic acid
  参考文献：
  名称：

  Noncovalent Tripeptidyl Benzyl- and Cyclohexyl-Amine Inhibitors of the Cysteine Protease Caspase-1

  摘要：

  Potent and noncovalent inhibitors of caspase-1 were produced by incorporating a secondary amine (reduced amide) isostere in place of the conventional electrophile (e.g., aldehyde) that normally confers high potency to cysteine protease inhibitors. Benzyl- or cyclohexylamines produced potent, reversible, and competitive inhibitors that were selective for caspase-1 (e.g., K-i = 47 nM) over caspases 3 and 8 with minimal cytotoxicity. Unlike most cysteine protease inhibitors, these compounds do not react covalently and indiscriminately with thiols.

  DOI：

  10.1021/jm901790w

文献信息

• A novel approach to homochiral β-amino acids
  作者：Masahiko Seki、Kazuo Matsumoto

  DOI：10.1016/0040-4039(96)00518-7

  日期：1996.4

  An efficient synthesis of γ-aryl or alkyl substituted β-amino acids starting from N-Cbz-L-homoserine lactone via the formation of α-amino aryl, alkenyl or alkynyl ketones with the original α-carbon chirality retained as such is described.

  描述了从N -Cbz-L-高丝氨酸内酯开始，通过形成保留了原始α-碳手性的α-氨基芳基，烯基或炔基酮，有效合成γ-芳基或烷基取代的β-氨基酸的方法。
• Noncovalent Tripeptidyl Benzyl- and Cyclohexyl-Amine Inhibitors of the Cysteine Protease Caspase-1
  作者：Reik Löser、Giovanni Abbenante、Praveen K. Madala、Maria Halili、Giang T. Le、David P. Fairlie

  DOI：10.1021/jm901790w

  日期：2010.3.25

  Potent and noncovalent inhibitors of caspase-1 were produced by incorporating a secondary amine (reduced amide) isostere in place of the conventional electrophile (e.g., aldehyde) that normally confers high potency to cysteine protease inhibitors. Benzyl- or cyclohexylamines produced potent, reversible, and competitive inhibitors that were selective for caspase-1 (e.g., K-i = 47 nM) over caspases 3 and 8 with minimal cytotoxicity. Unlike most cysteine protease inhibitors, these compounds do not react covalently and indiscriminately with thiols.