(3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-6-(3-nitroguanidino)hexanoic acid | 186370-73-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-6-(3-nitroguanidino)hexanoic acid
• CAS: 186370-73-0
• 化学式: C₁₂H₂₃N₅O₇
• 分子量: 349.344
• InChiKey: FRTHDAZCVUNTBU-JAMMHHFISA-N

物化性质

• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  189.41
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-6-(3-nitroguanidino)hexanoic acid 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 溶剂黄146 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Peptide inhibitors of dengue virus NS3 protease. Part 1: Warhead

  摘要：

  Substrate-based tetrapeptide inhibitors with various warheads were designed, synthesized, and evaluated against the Dengue virus NS3 protease. Effective inhibition was achieved by peptide inhibitors with electrophilic warheads such as aldehyde, trifluoromethyl ketone, and boronic acid. A boronic acid has the highest affinity, exhibiting a K-i of 43 nM. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.062
• 作为产物：
  描述：

  在 盐酸 、 lithium hydroxide 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 生成 (3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-6-(3-nitroguanidino)hexanoic acid
  参考文献：
  名称：

  Peptide inhibitors of dengue virus NS3 protease. Part 1: Warhead

  摘要：

  Substrate-based tetrapeptide inhibitors with various warheads were designed, synthesized, and evaluated against the Dengue virus NS3 protease. Effective inhibition was achieved by peptide inhibitors with electrophilic warheads such as aldehyde, trifluoromethyl ketone, and boronic acid. A boronic acid has the highest affinity, exhibiting a K-i of 43 nM. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.062

文献信息

• New Synthetic Technology for Efficient Construction of α-Hydroxy-β-amino Amides via the Passerini Reaction¹
  作者：J. Edward Semple、Timothy D. Owens、Khanh Nguyen、Odile E. Levy

  DOI：10.1021/ol0061485

  日期：2000.9.1

  [reaction: see text] The Passerini reaction of N-protected amino aldehydes, isonitriles, and TFA using pyridine-type bases proceeds under mild conditions and directly affords alpha-hydroxy-beta-amino amide derivatives in moderate to high yields. These adducts are readily hydrolyzed to alpha-hydroxy-beta-amino carboxylic acids. Application of these key intermediates to concise syntheses of P(1)-alpha-ketoamide

  [反应：见正文]使用吡啶型碱的N-保护的氨基醛，异腈和TFA的Passerini反应在温和的条件下进行，并以中等至高收率直接提供α-羟基-β-氨基酰胺衍生物。这些加合物容易水解成α-羟基-β-氨基羧酸。说明了这些关键中间体在简明P（1）-α-酮酰胺蛋白酶抑制剂合成中的应用。
• Synthesis and biological activity of P2–P4 azapeptidomimetic P1-argininal and P1-ketoargininamide derivatives: a novel class of serine protease inhibitors
  作者：J.Edward Semple、David C. Rowley、Terence K. Brunck、William C. Ripka

  DOI：10.1016/s0960-894x(97)00005-x

  日期：1997.2

  Molecular modeling and topographic considerations of the thrombin-specific sequences Boc-Asp-Pro-Arg-TS or Ac-d-Phe-Pro-Arg-TS (TS = transition state analog electrophilic center) and related scaffolds led to the design of novel P-2-P-4-azapeptidomimetic P-1-argininal and P-1-ketoargininamide derivatives (3a-j). The synthesis and biological activity of these potential serine protease inhibitors are presented. (C) 1997, Elsevier Science Ltd.
• RATIONAL DESIGN, SYNTHESIS, AND SERINE PROTEASE INHIBITORY ACTIVITY OF NOVEL P1-ARGININOYL HETEROCYCLES
  作者：Susan Y Tamura、Brian M Shamblin、Terence K Brunck、William C Ripka

  DOI：10.1016/s0960-894x(97)00227-8

  日期：1997.5

  Peptidomimetic derivatives featuring a P-1-argininoyl heterocycle were designed. The preparation of two key building blocks containing benzoxazole or benzimidazole rings and their incorporation into thrombin and factor Xa specific sequences is described. The serine protease inhibitory activity of these targets was evaluated. Molecular modeling of two representative structures is presented. (C) 1997 Elsevier Science Ltd.