3(S),2(R)-N-[(1,1-dimethylethoxy)carbonyl]-3-amino-2-hydroxy-4-phenylbutyronitrile | 105116-40-3

• 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(S),2(R)-N-[(1,1-dimethylethoxy)carbonyl]-3-amino-2-hydroxy-4-phenylbutyronitrile
• 英文别名: tert-butyl [(1S,2R)-1-benzyl-2-cyano-2-hydroxyethyl]carbamate；tert-butyl N-[(1R,2S)-1-cyano-1-hydroxy-3-phenylpropan-2-yl]carbamate
• CAS: 105116-40-3
• 化学式: C₁₅H₂₀N₂O₃
• 分子量: 276.335
• InChiKey: WACJTFSTSJLBSQ-STQMWFEESA-N

物化性质

• 沸点：
  489.4±45.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3(S),2(R)-N-[(1,1-dimethylethoxy)carbonyl]-3-amino-2-hydroxy-4-phenylbutyronitrile 在 盐酸 、 sodium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 diborane(6) 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 80.0h， 生成 5-chloro-N-[(2S,3R)-3,4-dihydroxy-1-phenylbutan-2-yl]-1H-indole-2-carboxamide
  参考文献：
  名称：

  人肝糖原磷酸化酶的吲哚-2-羧酰胺抑制剂。

  摘要：

  DOI：

  10.1021/jm980264k
• 作为产物：
  描述：

  N-叔丁氧羰基-L-苯丙氨酸甲酯 在 二异丁基氢化铝 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 生成 3(S),2(R)-N-[(1,1-dimethylethoxy)carbonyl]-3-amino-2-hydroxy-4-phenylbutyronitrile
  参考文献：
  名称：

  Nonpeptidic Lysosomal Modulators Derived from Z-Phe-Ala-Diazomethylketone for Treating Protein Accumulation Diseases

  摘要：

  Lysosomes are involved in protein turnover and removing misfolded species, and their enzymes have the potential to offset the defect in proteolytic clearance that contributes to the age-related dementia Alzheimer's disease (AD). The weak cathepsin B and L inhibitor Z-Phe-Ala-diazomethylketone (PADK) enhances lysosomal cathepsin levels at low concentrations, thereby eliciting protective clearance of PHF-tau and A beta 42 in the hippocampus and other brain regions. Here, a class of positive modulators is established with compounds decoupled from the cathepsin inhibitory properties. We utilized PADK as a departure point to develop nonpeptidic structures with the hydroxyethyl isostere. The first-in-class modulators SD1002 and SD1003 exhibit: : improved levels of cathepsin up-regulation but almost complete removal of cathepsin inhibitory properties as compared to PADK. Isomers of the lead compound SD1002 were synthesized, and the modulatory activity was determined to be stereoselective. In addition, the lead compound was tested in transgenic mice with results indicating protection against AD-type protein accumulation pathology.

  DOI：

  10.1021/ml300197h

文献信息

• Substituted n-(indole-2-carbonyl-) amides and derivatives as glycogen phosphorylase inhibitors
  申请人：Pfizer Inc.

  公开号：US06297269B1

  公开（公告）日：2001-10-02

  Compounds of the formula I: and their compositions are useful as glycogen phosphorylase inhibitors.

  公式I的化合物及其组合物可用作糖原磷酸化酶抑制剂。
• Unique Stereocontrol in Europium(III)-Catalyzed Cyanosilylation of Chiral α-Alkoxy and α-Amino Aldehydes
  作者：Jin-Hua Gu、Mikako Okamoto、Masahiro Terada、Koichi Mikami、Takeshi Nakai

  DOI：10.1246/cl.1992.1169

  日期：1992.7

  The Eu(III)-catalyzed cyanosilylations of chiral α-alkoxy and α-amino aldehydes are shown to exhibit syn diastereofacial selection, the degree increasing with an increase in steric bulk of the alkyl chain in the aldehydes. The mechanism of this catalytic process is discussed.

  研究表明，Eu(III)催化的手性α-烷氧基和α-氨基醛的氰硅化反应展现出了syn二面体选择性，且随着醛中烷基链空间位阻的增加，其选择性也增强。同时还讨论了这一催化过程的机理。
• Amino acid derivatives having renin inhibiting activity
  申请人：Hoffmann-La Roche Inc.

  公开号：US05393875A1

  公开（公告）日：1995-02-28

  The compounds of the formula ##STR1## wherein A, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the significance given in claim 1, in the form of optically pure diastereomers, mixtures of diastereomers, diastereomeric racemates or mixtures of diastereomeric racemates as well as pharmaceutically usable salts thereof inhibit the activity of the natural enzyme renin and can accordingly be used in the form of pharamaceutical preparations in the control or prevention of high blood pressure and cardiac insufficiency. They can be manufactured according to various methods which are known per se.

  该式的化合物##STR1##，其中A、R.sup.1、R.sup.2、R.sup.3、R.sup.4和R.sup.5的含义如权利要求1所述，在光学纯的对映体、对映体混合物、对映体拉克酸盐或对映体拉克酸盐混合物的形式中，抑制天然酶肾素的活性，并因此可以用作药用制剂的形式，用于控制或预防高血压和心脏功能不全。它们可以根据已知的各种方法制造。
• Orally active renin inhibitors
  申请人：PFIZER INC.

  公开号：EP0438233A2

  公开（公告）日：1991-07-24

  This invention relates to compounds of the formula wherein Q, Z, D, E, R3, R4, R5 and R6 are defined as below, and the pharmaceutically acceptable salts thereof are disclosed. The compounds are useful as antihypertensive agents.

  本发明涉及如下式的化合物 其中 Q、Z、D、E、R3、R4、R5 和 R6 的定义如下，本发明公开了其药学上可接受的盐类。这些化合物可用作降压药。
• HOOVER, DENNIS J.
  作者：HOOVER, DENNIS J.

  DOI：——

  日期：——