(2RS,3S)-3-(benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanenitrile | 243842-83-3

• 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: (2RS,3S)-3-(benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanenitrile
• 英文别名: benzyl N-[(2S)-1-cyano-1-hydroxy-3-phenylpropan-2-yl]carbamate
• CAS: 243842-83-3
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: LYNUWPBDPHNCGM-BHWOMJMDSA-N

物化性质

• 沸点：
  570.7±50.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  (2RS,3S)-3-(benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanenitrile 在 palladium on activated charcoal 盐酸 、 氢气 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙酸乙酯 、 乙腈 为溶剂， 生成 (2S)-1-[(3S)-3-amino-2-hydroxy-4-phenylbutanoyl]-N-tert-butylpyrrolidine-2-carboxamide
  参考文献：
  名称：

  Development of a New Type of Protease Inhibitors, Efficacious against FIV and HIV Variants

  摘要：

  Based on the structural analysis of FIV protease and drug-resistant HIV proteases and molecular modeling, a new type of inhibitors with a small P3 residue has been developed. These inhibitors are effective against HIV and its drug-resistant mutants, as well as SIV and FIV. Modification of existing HIV protease inhibitors by reducing the size of the P3 residue has the same effect. This finding provides a new strategy for the development of HIV protease inhibitors effective against the wild-type and drug-resistant mutants. It further supports the use of FIV protease as a useful model for drug-resistant HIV proteases, which often have a more constricted binding region for the P3 group or the combined P3 and P1 groups.

  DOI：

  10.1021/ja982893p
• 作为产物：
  描述：

  Z-L-苯丙氨醇 在 swern reagent 、 sodium hydrogensulfite 作用下， 生成 (2RS,3S)-3-(benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanenitrile
  参考文献：
  名称：

  Development of a New Type of Protease Inhibitors, Efficacious against FIV and HIV Variants

  摘要：

  Based on the structural analysis of FIV protease and drug-resistant HIV proteases and molecular modeling, a new type of inhibitors with a small P3 residue has been developed. These inhibitors are effective against HIV and its drug-resistant mutants, as well as SIV and FIV. Modification of existing HIV protease inhibitors by reducing the size of the P3 residue has the same effect. This finding provides a new strategy for the development of HIV protease inhibitors effective against the wild-type and drug-resistant mutants. It further supports the use of FIV protease as a useful model for drug-resistant HIV proteases, which often have a more constricted binding region for the P3 group or the combined P3 and P1 groups.

  DOI：

  10.1021/ja982893p

文献信息

• IgE ANTIBODY PRODUCTION INHIBITORS AND AUTOIMMUNE DISEASES INHIBITORS
  申请人：Welfide Corporation

  公开号：EP1062949A1

  公开（公告）日：2000-12-27

  The present invention relates to an IgE antibody production inhibitor and an autoimmune disease suppressant containing a heterocyclic amide compound represented by the following general formula (1) or a pharmaceutically acceptable salt thereof as an active ingredient wherein R represents a hydrogen atom, alkyl, -CHO, -COOH, etc.; R5, R6 and R7 represent each hydrogen, alkyl, aryl, etc.; M represents a carbon atom or a nitrogen atom; Y represents aryl, etc.; and Z represents hydrogen, alkyl, aryl, etc.

  本发明涉及一种 IgE 抗体产生抑制剂和一种自身免疫性疾病抑制剂，其活性成分含有下 列通式 (1) 所代表的杂环酰胺化合物或其药学上可接受的盐 其中 R 代表氢原子、烷基、-CHO、-COOH 等；R5、R6 和 R7 分别代表氢、烷基、芳基等；M 代表碳原子或氮原子；Y 代表芳基等；Z 代表氢、烷基、芳基等。
• Inactivation of serine protease, α-chymotrypsin by fluorinated phenylalanine analogues
  作者：Tsuyoshi Ohba、Eitatsu Ikeda、Hisashi Takei

  DOI：10.1016/0960-894x(96)00342-3

  日期：1996.8

  Fluorinated phenylalanine analogues were found to be slow-binding or reversible competitive inhibitors of alpha-chymotrypsin. A series of these compounds were designed to inactivate alpha-chymotrypsin as a result of the formation of hydrogen-bonding between fluorine atom of the inhibitors and the amide protons known as oxy-anion hole in the active-site of serine and cysteine proteases. Copyright (C) 1996 Elsevier Science Ltd
• US6528514B1
  申请人：——

  公开号：US6528514B1

  公开（公告）日：2003-03-04
• US6713472B1
  申请人：——

  公开号：US6713472B1

  公开（公告）日：2004-03-30
• US6960575B2
  申请人：——

  公开号：US6960575B2

  公开（公告）日：2005-11-01