3-氨基-2-羟基丁酸甲酯 | 106746-17-2

• 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
• 中文名称: 3-氨基-2-羟基丁酸甲酯
• 英文名称: methyl 3-amino-2-hydroxybutanoate
• CAS: 106746-17-2
• 化学式: C₅H₁₁NO₃
• 分子量: 133.147
• InChiKey: ZWEUQQKBVZDPQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  235.6±25.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氨基-2-羟基丁酸甲酯 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 2.92h， 生成 N-acetyl-L-prolyl-L-alanyl-N-(3-methoxy-1-methyl-2,3-dioxopropyl)-L-prolinamide
  参考文献：
  名称：

  Synthesis of peptidyl fluoromethyl ketones and peptidyl .alpha.-keto esters as inhibitors of porcine pancreatic elastase, human neutrophil elastase, and rat and human neutrophil cathepsin G

  摘要：

  Comparison of MeO-Suc-Val-Pro-Phe-CO2Me (29) and MeO-Suc-Ala-Ala-Pro-Phe- CO2Me (25) with their corresponding trifluoromethyl ketones 9a and 9b, respectively, in rat and human neutrophil cathepsin G assays showed the alpha-keto esters to be more potent inhibitors. Likewise, Ac-Pro-Ala-Pro-Ala-CO2Me (21) was more potent than its corresponding trifluoromethyl ketone (9c) in both porcine pancreatic elastase and human neutrophil elastase assays. Within a set of Ala-Ala-Pro-Val-CF3 elastase inhibitors, the carbobenzyloxy (Cbz) N-protecting group conferred greater potency as a P5 site recognition unit for elastase than did dansyl, methoxysuccinyl, or tert-butyloxycarbonyl. Initial inhibition of elastase was greater when trifluoromethyl ketone 9f was added from a stock solution of dimethyl sulfoxide than when it had been buffer-equilibrated prior to assay, which suggests that the nonhydrated ketone is the more effective form of the inhibitor. The most potent elastase inhibitor we report is Na-(Ad-SO2)-N epsilon-(MeO-Suc)Lys-Pro-Val-CF3 (16) which has a Ki of 0.58 nM.

  DOI：

  10.1021/jm00163a063
• 作为产物：
  描述：

  (3-S)-3-Amino-2-hydroxybutanoic acid 生成 3-氨基-2-羟基丁酸甲酯
  参考文献：
  名称：

  PEET, NORTON P.;BURKHART, JOSEPH P.;ANGELASTRO, MICHAEL R.;GIROUX, EUGENE+, J. MED. CHEM., 33,(1990) N, C. 394-407

  摘要：

  DOI：

文献信息

• Trifluoromethylphenyl as P2 for ketoamide-based cathepsin S inhibitors
  作者：Jiaqiang Cai、John Robinson、Simone Belshaw、Kathryn Everett、Xavier Fradera、Mario van Zeeland、Leon van Berkom、Peter van Rijnsbergen、Lucy Popplestone、Mark Baugh、Maureen Dempster、John Bruin、William Hamilton、Emma Kinghorn、Paul Westwood、Jennifer Kerr、Zoran Rankovic、Wullie Arbuckle、D. Jonathan Bennett、Philip S. Jones、Clive Long、Iain Martin、Joost C.M. Uitdehaag、Tommi Meulemans

  DOI：10.1016/j.bmcl.2010.10.012

  日期：2010.12

  The trifluoromethylphenyl P2 motif from previously reported heteroarylnitrile series has been successfully applied for the design and synthesis of highly potent novel ketoamide-based cathepsin S inhibitors. The key in this process is the change of the torsion angle between the P2 phenyl ring and the attached secondary amide by adding a small Cl, F, or Me group at the 2-position. (C) 2010 Elsevier Ltd. All rights reserved.