2-(5-nitro-1H-indol-1-yl)ethanol | 578725-96-9

• 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: 2-(5-nitro-1H-indol-1-yl)ethanol
• 英文别名: 2-(5-Nitroindol-1-yl)ethanol
• CAS: 578725-96-9
• 化学式: C₁₀H₁₀N₂O₃
• 分子量: 206.201
• InChiKey: GHIRDRNMZFKKQG-UHFFFAOYSA-N

物化性质

• 沸点：
  421.7±25.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-nitro-1H-indol-1-yl)ethanol 在 calcium sulfate 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 二苯醚 、 乙醇 、 乙酸乙酯 为溶剂， 50.0~250.0 ℃ 、101.33 kPa 条件下， 反应 39.25h， 生成 3-(2-hydroxyethyl)-7-phenyl-3H-pyrrolo[3,2-f]quinolin-9(6H)-one
  参考文献：
  名称：

  Novel 3-Substituted 7-Phenylpyrrolo[3,2-f]quinolin-9(6H)-ones as Single Entities with Multitarget Antiproliferative Activity

  摘要：

  A series of chemically modified 7-phenylpyrrolo[3,2-f]quinolinones was synthesized and evaluated as anticancer agents. Among them, the most cytotoxic (subnanomolar GI(50) values) amidic derivative 5f was shown to act as an inhibitor of tubulin polymerization (IC50, 0.99 mu M) by binding to the colchicine site with high affinity. Moreover, 5f induced cell cycle arrest in the G2/M phase of the cell cycle in a concentration dependent manner, followed by caspase-dependent apoptotic cell death. Compound 5f also showed lower toxicity in nontumoral cells, suggesting selectivity toward cancer cells. Additional experiments revealed that 5f inhibited the enzymatic activity of multiple kinases, including AURKA, FLT3, GSK3A, MAP3K, MEK, RSK2, RSK4, PLK4, ULK1, and JAK1. Computational studies showed that 5f can be properly accommodated in the colchicine binding site of tubulin as well as in the ATP binding clefts of all examined kinases. Our data indicate that the excellent antiproliferative profile of 5f may be derived from its interactions with multiple cellular targets.

  DOI：

  10.1021/acs.jmedchem.5b00805
• 作为产物：
  描述：

  5-硝基吲哚 在 sodium hydride 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.5h， 生成 2-(5-nitro-1H-indol-1-yl)ethanol
  参考文献：
  名称：

  Tethered Dimers as NAD Synthetase Inhibitors with Antibacterial Activity

  摘要：

  The solution-phase parallel synthesis of tethered dimers was employed to identify lead inhibitors of bacterial NAD synthetase. Active dimers contained two aromatic end groups joined by a polymethylene linker, with one end group containing a permanent positive charge. Effective inhibitors of NAD synthetase also inhibited the growth of Gram-positive (but not Gram-negative) bacteria, including antibiotic-resistant strains. The desmethyl precursors of active inhibitors lacked a permanent positive charge and were inactive as either enzyme inhibitors or antibacterial agents. Similarly, a close structural analogue of the most active inhibitors contained two additional ether oxygens in the tether and was inactive in both assays. These results are consistent with the premise that NAD synthetase inhibition is responsible for the antibacterial actions and support further studies on NAD synthetase as a new target for antibacterial agents.

  DOI：

  10.1021/jm030003x