methyl (3S)-6-[[amino(nitramido)methylidene]amino]-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate | 187740-86-9

• 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: methyl (3S)-6-[[amino(nitramido)methylidene]amino]-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 187740-86-9
• 化学式: C₁₃H₂₅N₅O₇
• 分子量: 363.371
• InChiKey: OPMHCGZPBONORC-IENPIDJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.71
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  178.41
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl (3S)-6-[[amino(nitramido)methylidene]amino]-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 以95%的产率得到
  参考文献：
  名称：

  RATIONAL DESIGN, SYNTHESIS, AND SERINE PROTEASE INHIBITORY ACTIVITY OF NOVEL P1-ARGININOYL HETEROCYCLES

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(97)00227-8
• 作为产物：
  描述：

  甲醇 、 二碳酸二叔丁酯 、 在 盐酸 、 碳酸氢钠 作用下， 生成 methyl (3S)-6-[[amino(nitramido)methylidene]amino]-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
  参考文献：
  名称：

  RATIONAL DESIGN, SYNTHESIS, AND SERINE PROTEASE INHIBITORY ACTIVITY OF NOVEL P1-ARGININOYL HETEROCYCLES

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(97)00227-8

文献信息

• 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.
• Peptide inhibitors of dengue virus NS3 protease. Part 1: Warhead
  作者：Zheng Yin、Sejal J. Patel、Wei-Ling Wang、Gang Wang、Wai-Ling Chan、K.R. Ranga Rao、Jenefer Alam、Duraiswamy A. Jeyaraj、Xinyi Ngew、Viral Patel、David Beer、Siew Pheng Lim、Subhash G. Vasudevan、Thomas H. Keller

  DOI：10.1016/j.bmcl.2005.09.062

  日期：2006.1

  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.