E-64c | 1056464-93-7

• 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: E-64c
• 英文别名: (2R,3S)-3-[[(2S)-4-methyl-1-(3-methylbutylamino)-1-oxopentan-2-yl]carbamoyl]oxirane-2-carboxylic acid
• CAS: 1056464-93-7
• 化学式: C₁₅H₂₆N₂O₅
• 分子量: 314.382
• InChiKey: SCMSYZJDIQPSDI-SDDRHHMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  E-64c 、 乙醇 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以30%的产率得到loxistatine
  参考文献：
  名称：

  Stereoselective synthesis of E-64 and related cysteine proteases inhibitors from 2,3-epoxyamides

  摘要：

  The stereoselective synthesis of cathepsin inhibitors from indoline type epoxyamides is described. The use of this type of epoxyamides permitted the preparation of E-64 and CA-074 related compounds depending on the order in which the key steps, the oxidation of indoline amides to indole amides and oxidative acetal cleavage were undertaken. By taking advantage of the facile substitution of the indole of the corresponding indole epoxyamides, with various nucleophiles, we were able to prepare different epoxysuccinic acids derivatives as potential cathepsin inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.018
• 作为产物：
  描述：

  在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 以82%的产率得到E-64c
  参考文献：
  名称：

  Stereoselective synthesis of E-64 and related cysteine proteases inhibitors from 2,3-epoxyamides

  摘要：

  The stereoselective synthesis of cathepsin inhibitors from indoline type epoxyamides is described. The use of this type of epoxyamides permitted the preparation of E-64 and CA-074 related compounds depending on the order in which the key steps, the oxidation of indoline amides to indole amides and oxidative acetal cleavage were undertaken. By taking advantage of the facile substitution of the indole of the corresponding indole epoxyamides, with various nucleophiles, we were able to prepare different epoxysuccinic acids derivatives as potential cathepsin inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.018

文献信息

• Stereoselective synthesis of E-64 and related cysteine proteases inhibitors from 2,3-epoxyamides
  作者：Francisco Sarabia、Antonio Sánchez-Ruiz、Samy Chammaa

  DOI：10.1016/j.bmc.2004.12.018

  日期：2005.3.1

  The stereoselective synthesis of cathepsin inhibitors from indoline type epoxyamides is described. The use of this type of epoxyamides permitted the preparation of E-64 and CA-074 related compounds depending on the order in which the key steps, the oxidation of indoline amides to indole amides and oxidative acetal cleavage were undertaken. By taking advantage of the facile substitution of the indole of the corresponding indole epoxyamides, with various nucleophiles, we were able to prepare different epoxysuccinic acids derivatives as potential cathepsin inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.