(2S)-2-{2-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]acetylamino}pentanedioic acid dimethyl ester | 1571842-11-9

• 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: (2S)-2-{2-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]acetylamino}pentanedioic acid dimethyl ester
• CAS: 1571842-11-9
• 化学式: C₂₄H₂₄N₂O₈S
• 分子量: 500.529
• InChiKey: KVBMVFBQTPCVFF-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  137.84
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S)-2-{2-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]acetylamino}pentanedioic acid dimethyl ester 在 水 、 sodium hydroxide 作用下， 以 丙酮 为溶剂， 以85%的产率得到(2S)-2-{2-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]acetylamino}pentanedioic acid
  参考文献：
  名称：

  Lead modification: Amino acid appended indoles as highly effective 5-LOX inhibitors

  摘要：

  N-1 tosyl indoles carrying amino acid as a part of C-3 substituent are identified with considerable 5-LOX inhibitory activities. On the basis of enzyme inhibitory activities and log P, it is found that these compounds are more suitable to use as ester prodrugs. In addition to the significant K-a and K-i for 5-LOX, advantageously the compounds under present investigation do not affect the viability of the cell. The experimental results were also supported by molecular docking of compounds in the active site of 5-LOX. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.027
• 作为产物：
  描述：

  吲哚 在 sodium hydride 、 potassium carbonate 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 0.5h， 生成 (2S)-2-{2-oxo-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]acetylamino}pentanedioic acid dimethyl ester
  参考文献：
  名称：

  Lead modification: Amino acid appended indoles as highly effective 5-LOX inhibitors

  摘要：

  N-1 tosyl indoles carrying amino acid as a part of C-3 substituent are identified with considerable 5-LOX inhibitory activities. On the basis of enzyme inhibitory activities and log P, it is found that these compounds are more suitable to use as ester prodrugs. In addition to the significant K-a and K-i for 5-LOX, advantageously the compounds under present investigation do not affect the viability of the cell. The experimental results were also supported by molecular docking of compounds in the active site of 5-LOX. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.027