β-ethylenacetal of 1-(3,3-dimethyl-2-oxobutyl)indole-2,3-dione | 300588-82-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: β-ethylenacetal of 1-(3,3-dimethyl-2-oxobutyl)indole-2,3-dione
• 英文别名: 1'-(3,3-Dimethyl-2-oxobutyl)spiro[1,3-dioxolane-2,3'-indole]-2'-one
• CAS: 300588-82-3
• 化学式: C₁₆H₁₉NO₄
• mdl: MFCD00633115
• 分子量: 289.331
• InChiKey: MNPZLRXLBGZPCI-UHFFFAOYSA-N

物化性质

• 沸点：
  496.7±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  β-ethylenacetal of 1-(3,3-dimethyl-2-oxobutyl)indole-2,3-dione 在 盐酸 作用下， 以 乙醇 为溶剂， 以60%的产率得到1-(3,3-dimethyl-2-oxobutyl)indole-2,3-dione
  参考文献：
  名称：

  Synthesis of 2-(2,2-dimethyl-1-oxopropyl)-indole-3-carboxylic acid by the indoledione-indole rearrangement method in NaOH/AQ. DMSO

  摘要：

  DOI：

  10.1007/bf02315194
• 作为产物：
  描述：

  螺[1,3-二氧戊环-2,3'-[3H]吲哚]-2'(1'H)-酮 、 1-溴频哪酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到β-ethylenacetal of 1-(3,3-dimethyl-2-oxobutyl)indole-2,3-dione
  参考文献：
  名称：

  Discovery and Optimization of Two Eis Inhibitor Families as Kanamycin Adjuvants against Drug-Resistant M. tuberculosis

  摘要：

  Drug-resistant tuberculosis (TB) is a global threat and innovative approaches such as using adjuvants of anti-TB therapeutics are required to combat it. High-throughput screening yielded two lead scaffolds of inhibitors of Mycobacterium tuberculosis (Mtb) acetyltransferase Eis, whose upregulation causes resistance to the anti-TB drug kanamycin (KAN). Chemical optimization on these scaffolds resulted in potent Eis inhibitors. One compound restored the activity of KAN in a KAN-resistant Mtb strain. Model structures of Eis-inhibitor complexes explain the structure activity relationship.

  DOI：

  10.1021/acsmedchemlett.6b00261

文献信息

• Discovery and Optimization of Two Eis Inhibitor Families as Kanamycin Adjuvants against Drug-Resistant <i>M. tuberculosis</i>
  作者：Atefeh Garzan、Melisa J. Willby、Keith D. Green、Oleg V. Tsodikov、James E. Posey、Sylvie Garneau-Tsodikova

  DOI：10.1021/acsmedchemlett.6b00261

  日期：2016.12.8

  Drug-resistant tuberculosis (TB) is a global threat and innovative approaches such as using adjuvants of anti-TB therapeutics are required to combat it. High-throughput screening yielded two lead scaffolds of inhibitors of Mycobacterium tuberculosis (Mtb) acetyltransferase Eis, whose upregulation causes resistance to the anti-TB drug kanamycin (KAN). Chemical optimization on these scaffolds resulted in potent Eis inhibitors. One compound restored the activity of KAN in a KAN-resistant Mtb strain. Model structures of Eis-inhibitor complexes explain the structure activity relationship.
• Synthesis of 2-(2,2-dimethyl-1-oxopropyl)-indole-3-carboxylic acid by the indoledione-indole rearrangement method in NaOH/AQ. DMSO
  作者：M. A. Rekhter、B. A. Rekhter、I. G. Yazlovetskii、A. A. Panasenko

  DOI：10.1007/bf02315194

  日期：1998.2