methyl 6-(4-(1H-indol-1-ylsulfonyl)phenyl)-1-hydroxy-1H-indole-2-carboxylate | 1350916-19-6

• 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 6-(4-(1H-indol-1-ylsulfonyl)phenyl)-1-hydroxy-1H-indole-2-carboxylate
• CAS: 1350916-19-6
• 化学式: C₂₄H₁₈N₂O₅S
• 分子量: 446.483
• InChiKey: IWTVQGWRCYWWHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  32.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  90.53
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 6-(4-(1H-indol-1-ylsulfonyl)phenyl)-1-hydroxy-1H-indole-2-carboxylate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以44%的产率得到6-(4-(1H-indol-1-ylsulfonyl)phenyl)-1-hydroxy-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-溴苯磺酰氯 在 tin(II) chloride dihdyrate 、 四丁基硫酸氢铵 、 palladium diacetate 、 sodium hydride 、 sodium carbonate 、 苯硫酚 、 三乙胺 、 三苯基膦 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 0.08h， 生成 methyl 6-(4-(1H-indol-1-ylsulfonyl)phenyl)-1-hydroxy-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