3-Amino-2-hydroxy-4-phenylbutanenitrile | 176751-62-5

• 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: 3-Amino-2-hydroxy-4-phenylbutanenitrile
• CAS: 176751-62-5
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: OICVFXGCUDALIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Amino-2-hydroxy-4-phenylbutanenitrile 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 3-氨基-2-羟基-4-苯丁酰胺
  参考文献：
  名称：

  Synthesis and biological evaluation of novel piperidine carboxamide derived calpain inhibitors

  摘要：

  Calpain inhibitors which are derived from piperidine carboxamides in the P-2 legion were prepared and evaluated for mu-calpain inhibition. In particular, the keto amides 11f and 11j have K-i of 30 and 9 nM and display a more than 100-fold selectivity over the closely related cysteine protease cathepsin B. Furthermore, these compounds inhibit NMDA induced convulsions in mice indicating that calpain inhibition in brain results in some anticonvulsive properties. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00430-3
• 作为产物：
  描述：

  DL-2-氨基-3-苯基-1-丙醇 在 三氧化硫吡啶 、 二甲基亚砜 作用下， 生成 3-Amino-2-hydroxy-4-phenylbutanenitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of novel piperidine carboxamide derived calpain inhibitors

  摘要：

  Calpain inhibitors which are derived from piperidine carboxamides in the P-2 legion were prepared and evaluated for mu-calpain inhibition. In particular, the keto amides 11f and 11j have K-i of 30 and 9 nM and display a more than 100-fold selectivity over the closely related cysteine protease cathepsin B. Furthermore, these compounds inhibit NMDA induced convulsions in mice indicating that calpain inhibition in brain results in some anticonvulsive properties. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00430-3

文献信息

• Process for the preparation of 3-amino-2-hydroxy-4-phenylbutyronitrile derivatives
  申请人：KURARAY CO., LTD.

  公开号：EP0849257A1

  公开（公告）日：1998-06-24

  According to the present invention, there is provided a process for the preparation of a 3-amino-2-hydroxy-4-phenylbutyronitrile derivative represented by the formula (3), which comprises reacting an aminoaldehyde derivative represented by the formula (1) with a cyanohydrin derivative represented by the formula (2) in the presence of a metallic compound, base or acid; wherein R1 and R2 each independently represents a hydrogen atom or a protective group for an amino group, R3 and R4 each represents an alkyl or cycloalkyl group or R3 and R4 may be coupled together to form a tetramethylene or pentamethylene group.

  根据本发明，提供了一种制备式(3)代表的 3-氨基-2-羟基-4-苯基丁腈衍生物 的工艺，该工艺包括在金属化合物、碱或酸存在下，使式(1)代表的氨基醛衍生物 与式(2)代表的氰醇衍生物反应； 其中 R1 和 R2 各自独立地代表一个氢原子或一个氨基的保护基团，R3 和 R4 各自代表一个烷基或环烷基，或 R3 和 R4 可连接在一起形成一个四亚甲基或五亚甲基。
• US4189604A
  申请人：——

  公开号：US4189604A

  公开（公告）日：1980-02-19
• US4240975A
  申请人：——

  公开号：US4240975A

  公开（公告）日：1980-12-23
• US5834618A
  申请人：——

  公开号：US5834618A

  公开（公告）日：1998-11-10
• Synthesis and biological evaluation of novel piperidine carboxamide derived calpain inhibitors
  作者：W. Lubisch、H.P. Hofmann、H.J. Treiber、A. Möller

  DOI：10.1016/s0960-894x(00)00430-3

  日期：2000.10

  Calpain inhibitors which are derived from piperidine carboxamides in the P-2 legion were prepared and evaluated for mu-calpain inhibition. In particular, the keto amides 11f and 11j have K-i of 30 and 9 nM and display a more than 100-fold selectivity over the closely related cysteine protease cathepsin B. Furthermore, these compounds inhibit NMDA induced convulsions in mice indicating that calpain inhibition in brain results in some anticonvulsive properties. (C) 2000 Elsevier Science Ltd. All rights reserved.