methyl 1-hydroxy-6-(N-methyl-N-(4-(trifluoromethyl)phenyl)sulfamoyl)-1H-indole-2-carboxylate | 1303576-57-9

• 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: methyl 1-hydroxy-6-(N-methyl-N-(4-(trifluoromethyl)phenyl)sulfamoyl)-1H-indole-2-carboxylate
• 英文别名: Methyl 1-hydroxy-6-[methyl-[4-(trifluoromethyl)phenyl]sulfamoyl]indole-2-carboxylate
• CAS: 1303576-57-9
• 化学式: C₁₈H₁₅F₃N₂O₅S
• 分子量: 428.389
• InChiKey: OSNICTKUIHNCQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  97.2
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 1-hydroxy-6-(N-methyl-N-(4-(trifluoromethyl)phenyl)sulfamoyl)-1H-indole-2-carboxylate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以86%的产率得到1-hydroxy-6-(N-methyl-N-(4-(trifluoromethyl)phenyl)sulfamoyl)-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of sulfonamide-containing N-hydroxyindole-2-carboxylates as inhibitors of human lactate dehydrogenase-isoform 5

  摘要：

  N-Hydroxyindole-2-carboxylates possessing sulfonamide-substituents at either position 5 or 6 were designed and synthesized. The inhibitory activities of these compounds against isoforms 1 and 5 of human lactate dehydrogenase were analysed, and K-i values of the most efficient inhibitors were determined by standard enzyme kinetic studies. Some of these compounds displayed state-of-the-art inhibitory potencies against isoform 5 (K-i values as low as 5.6 mu M) and behaved as competitive inhibitors versus both the substrate and the cofactor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.031
• 作为产物：
  描述：

  4-甲基-3-硝基苯磺酰氯 在 吡啶 、 4-二甲氨基吡啶 、 lead 、 sodium hydride 、 甲酸:三乙胺 1:1 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成 methyl 1-hydroxy-6-(N-methyl-N-(4-(trifluoromethyl)phenyl)sulfamoyl)-1H-indole-2-carboxylate
  参考文献：
  名称：

  Synthesis of sulfonamide-containing N-hydroxyindole-2-carboxylates as inhibitors of human lactate dehydrogenase-isoform 5

  摘要：

  N-Hydroxyindole-2-carboxylates possessing sulfonamide-substituents at either position 5 or 6 were designed and synthesized. The inhibitory activities of these compounds against isoforms 1 and 5 of human lactate dehydrogenase were analysed, and K-i values of the most efficient inhibitors were determined by standard enzyme kinetic studies. Some of these compounds displayed state-of-the-art inhibitory potencies against isoform 5 (K-i values as low as 5.6 mu M) and behaved as competitive inhibitors versus both the substrate and the cofactor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.031