(2S)-2-[2-(1H-indol-3-yl)-2-oxoacetylamino]pentanedioic acid dimethyl ester | 1571841-83-2

• 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-(1H-indol-3-yl)-2-oxoacetylamino]pentanedioic acid dimethyl ester
• 英文别名: 2-[2-(1H-indol-3-yl)-2-oxoacetylamino]pentanedioic acid dimethyl ester；dimethyl (2-(1H-indol-3-yl)-2-oxoacetyl)glutamate；dimethyl (2S)-2-[[2-(1H-indol-3-yl)-2-oxoacetyl]amino]pentanedioate
• CAS: 1571841-83-2
• 化学式: C₁₇H₁₈N₂O₆
• 分子量: 346.34
• InChiKey: WQQBTNYLUGEZRL-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-2-[2-(1H-indol-3-yl)-2-oxoacetylamino]pentanedioic acid dimethyl ester 在 sodium hydride 、 sodium ascorbate 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 14.0h， 生成 dimethyl (2-(1-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-1H-indol-3-yl)-2oxoacetyl)glutamate
  参考文献：
  名称：

  Rational modification of a lead molecule: Improving the antifungal activity of indole – triazole – amino acid conjugates

  摘要：

  The modification of a molecule that was identified as highly efficacious in the previous studies could considerably improve the biological activity of the resulting compounds. While targeting lanosterol 14-alpha demethylase, the molecular modelling studies convinced that the extension of the phenyl ring of compound 1 deep into the hydrophobic pocket of the enzyme may increase the enzyme ligand interactions and hence improve the anti-fungal profile of the molecules. As a result, the newly designed compounds 2 were synthesized and screened for their anti-microbial properties and these compounds were found to exhibit considerably better activity than the previous molecule 1. Some of the compounds in this series exhibited MIC90 16 mu g mL(-1) and 32 mu g mL(-1) against Candida albicans and Aspergillus niger, respectively as against 312 mu g mL(-1) for compound 1. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.06.039
• 作为产物：
  描述：

  吲哚 在 potassium carbonate 作用下， 以 乙醚 、 乙腈 为溶剂， 生成 (2S)-2-[2-(1H-indol-3-yl)-2-oxoacetylamino]pentanedioic acid dimethyl ester
  参考文献：
  名称：

  Identification of an indole–triazole–amino acid conjugate as a highly effective antifungal agent

  摘要：

  通过将氨基酸和三唑与吲哚基团进行嫁接构建的化合物已合成并用于抗真菌活性研究，其中一种化合物表现出非常有前景的结果。

  DOI：

  10.1039/c5md00156k

文献信息

• Lead modification: Amino acid appended indoles as highly effective 5-LOX inhibitors
  作者：Parteek Prasher、Pooja、Palwinder Singh

  DOI：10.1016/j.bmc.2014.01.027

  日期：2014.3

  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.