1-((1-hydroxy-4-phenylbutan-2-ylcarbamoyl)-3-methylbutyl)morpholine-4-carboxamide | 1256776-41-6

• 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: 1-((1-hydroxy-4-phenylbutan-2-ylcarbamoyl)-3-methylbutyl)morpholine-4-carboxamide
• CAS: 1256776-41-6
• 化学式: C₂₁H₃₃N₃O₄
• 分子量: 391.511
• InChiKey: FTDWNXXDZNQRJV-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  28.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  90.9
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-((1-hydroxy-4-phenylbutan-2-ylcarbamoyl)-3-methylbutyl)morpholine-4-carboxamide 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以53%的产率得到1-((1-formyl-3-phenylpropylcarbamoyl)-3-methylbutyl)morpholine-4-carboxamide
  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-(4-methyl-2-(morpholine-4-carboxamido)pentanoylamino)-4-phenylbutanoic acid methyl ester 在 sodium tetrahydroborate 、 calcium chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 以92%的产率得到1-((1-hydroxy-4-phenylbutan-2-ylcarbamoyl)-3-methylbutyl)morpholine-4-carboxamide
  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