| 1303575-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• CAS: 1303575-44-1
• 化学式: C₂₀H₁₅NO₅
• 分子量: 349.343
• InChiKey: AAIBBPBESLBYSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  86.51
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 tin(II) chloride dihdyrate 、 苯硫酚 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 0.08h， 生成 1-hydroxy-6-(naphthalen-1-yl)-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  N-Hydroxyindole-based inhibitors of lactate dehydrogenase against cancer cell proliferation

  摘要：

  Current cancer research is being increasingly focused on the study of distinctive characters of tumour metabolism, resulting in a switch from oxidative phosphorylation to glycolysis (Warburg effect). Isoform 5 of human lactate dehydrogenase (hLDH5), which catalyzes the final step in the glycolytic cascade (pyruvate to lactate), constitutes a relatively new and untapped anti-cancer target. In this study, careful design and synthesis of a selected series of aryl-substituted N-hydroxyindole-2-carboxylates (NHIs) has led to several hLDH5-inhibitors, showing "first-in-class" potency and isoform selectivity. Enzyme kinetics studies indicated that these inhibitors exhibit a competitive mode of inhibition. Some representative examples were tested against two human pancreatic carcinoma cell lines, and displayed a good antiproliferative activity, which was even more evident under hypoxic conditions. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.046
• 作为产物：
  描述：

  4-溴-2-硝基甲苯 在 四丁基溴化铵 、 palladium diacetate 、 sodium hydride 、 sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  N-Hydroxyindole-based inhibitors of lactate dehydrogenase against cancer cell proliferation

  摘要：

  Current cancer research is being increasingly focused on the study of distinctive characters of tumour metabolism, resulting in a switch from oxidative phosphorylation to glycolysis (Warburg effect). Isoform 5 of human lactate dehydrogenase (hLDH5), which catalyzes the final step in the glycolytic cascade (pyruvate to lactate), constitutes a relatively new and untapped anti-cancer target. In this study, careful design and synthesis of a selected series of aryl-substituted N-hydroxyindole-2-carboxylates (NHIs) has led to several hLDH5-inhibitors, showing "first-in-class" potency and isoform selectivity. Enzyme kinetics studies indicated that these inhibitors exhibit a competitive mode of inhibition. Some representative examples were tested against two human pancreatic carcinoma cell lines, and displayed a good antiproliferative activity, which was even more evident under hypoxic conditions. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.046