methyl (2-(1H-indol-3-yl)-2-oxoacetyl)tyrosinate | 94732-20-4

• 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: methyl (2-(1H-indol-3-yl)-2-oxoacetyl)tyrosinate
• 英文别名: methyl (2S)-3-(4-hydroxyphenyl)-2-[[2-(1H-indol-3-yl)-2-oxoacetyl]amino]propanoate
• CAS: 94732-20-4
• 化学式: C₂₀H₁₈N₂O₅
• 分子量: 366.373
• InChiKey: FUJASGUZAYMJFC-KRWDZBQOSA-N

物化性质

• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2-(1H-indol-3-yl)-2-oxoacetyl)tyrosinate 在 sodium hydride 、 sodium ascorbate 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 14.0h， 生成 methyl (S)-3-(4-((1-benzyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-2-(2-(1-((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)-1Hindol-3-yl)-2-oxoacetamido)propanoate
  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， 反应 3.0h， 生成 methyl (2-(1H-indol-3-yl)-2-oxoacetyl)tyrosinate
  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

文献信息

• Synthetic studies towards oxazinins. An expedient first total synthesis and proof of the absolute stereochemistry of oxazinin-3
  作者：Elias A. Couladouros、Vassilios I. Moutsos、Emmanuel N. Pitsinos

  DOI：10.1016/j.tetlet.2004.08.054

  日期：2004.10

  A synthetic strategy, based on intramolecular addition of an appropriate hydroxyl substituent to a 3-methyleneindolenine, towards the naturally occurring marine toxins oxazinin-1, -2 and -3 is presented. The expedient first total synthesis of oxazinin-3, thus accomplished, demonstrated the efficiency of the approach and established the absolute stereochernistry of oxazinin-3 as 2S,5S. (C) 2004 Elsevier Ltd. All rights reserved.
• Rational modification of a lead molecule: Improving the antifungal activity of indole – triazole – amino acid conjugates
  作者：Sahil Mishra、Manpreet Kaur、Subhash Chander、Sankaranarayanan Murugesan、Lovedeep Nim、D.S. Arora、Palwinder Singh

  DOI：10.1016/j.ejmech.2018.06.039

  日期：2018.7

  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.