2-(2-{[(benzyloxy)carbonyl]amino}-4-methylpentanoylamino)-4-phenylbutanoic acid | 1256776-43-8

• 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
• 英文名称: 2-(2-{[(benzyloxy)carbonyl]amino}-4-methylpentanoylamino)-4-phenylbutanoic acid
• 英文别名: (2S)-2-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]-4-phenylbutanoic acid
• CAS: 1256776-43-8
• 化学式: C₂₄H₃₀N₂O₅
• 分子量: 426.513
• InChiKey: CFNLSPVEMBIQHA-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-{[(benzyloxy)carbonyl]amino}-4-methylpentanoylamino)-4-phenylbutanoic acid 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 magnesium 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 mercury dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 benzyl 1-(2-oxo-1-phenoxy-5-phenylpentan-3-ylcarbamoyl)-3-methylbutylcarbamate
  参考文献：
  名称：

  Endoperoxide Carbonyl Falcipain 2/3 Inhibitor Hybrids: Toward Combination Chemotherapy of Malaria through a Single Chemical Entity

  摘要：

  We extend our approach of combination chemotherapy through a single prodrug entity (O'Neill et al. Angew. Chem., Int. Ed. 2004, 43, 4193) by using a 1,2,4-trioxolane as a protease inhibitor carbonyl-masking group. These molecules are designed to target the malaria parasite through two independent mechanisms of action: iron(II) decomposition releases the carbonyl protease inhibitor and potentially eytotoxic C-radical species in tandem. Using a proposed target "heme", we also demonstrate heme alkylation/carbonyl inhibitor release and quantitatively measure endoperoxide turnover in parasitized red blood cells.

  DOI：

  10.1021/jm1009567
• 作为产物：
  描述：

  2-(2-{[(benzyloxy)carbonyl]amino}-4-methylpentanoylamino)-4-phenylbutanoic acid methyl ester 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以98%的产率得到2-(2-{[(benzyloxy)carbonyl]amino}-4-methylpentanoylamino)-4-phenylbutanoic acid
  参考文献：
  名称：

  Endoperoxide Carbonyl Falcipain 2/3 Inhibitor Hybrids: Toward Combination Chemotherapy of Malaria through a Single Chemical Entity

  摘要：

  We extend our approach of combination chemotherapy through a single prodrug entity (O'Neill et al. Angew. Chem., Int. Ed. 2004, 43, 4193) by using a 1,2,4-trioxolane as a protease inhibitor carbonyl-masking group. These molecules are designed to target the malaria parasite through two independent mechanisms of action: iron(II) decomposition releases the carbonyl protease inhibitor and potentially eytotoxic C-radical species in tandem. Using a proposed target "heme", we also demonstrate heme alkylation/carbonyl inhibitor release and quantitatively measure endoperoxide turnover in parasitized red blood cells.

  DOI：

  10.1021/jm1009567